Inside The ‘Insecure’ World | HuffPost Entertainment

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Issa Rae knows how to build a space to innovate and elevate. The 36-year-old actor, who in 2016 became the first Black woman to create and star in her own premium cable show, is wrapping up the fifth and final season of the groundbreaking HBO series “Insecure.” The Emmy Award-winning show’s impact — on Hollywood, on its cast and crew, on its audience — is almost impossible to measure.

“Insecure” has forever changed what it means to decenter whiteness on television and to position people of color and other marginalized groups at the center of their stories — in front of and behind the camera. Building that runway for talent is part of the enduring legacy of “Insecure,” and for Rae and showrunner Prentice Penny, cultivating an inclusive atmosphere was intentional at every step of the way.

That approach — taking chances on new talent, elevating creatives up the corporate ladder, and exploring hot topics in life, love and friendships — has already paid off for so many in the Issa Rae universe: Her co-stars Jay Ellis and Natasha Rothwell directed episodes of the series; writers Syreeta Singleton, Dayna Lynne North, Phil Augusta Jackson and others have inked deals with networks to develop TV shows. And several people who previously collaborated with Rae on her “Awkward Black Girl” web series — Amy Aniobi, Sujata Day, Tristen J. Winger — are starring in and building out other projects.

The success of “Insecure” proved to Hollywood that audiences want more real stories about everyday people, especially characters who look and sound just like them.

In this HuffPost project, we talked to dozens of “Insecure” actors, writers and directors who raved about their collaborative, inspiring and hella fun experiences working on the series. We learned fun facts about the audition process (several cast members auditioned to be Lawrence), reminisced on the team’s most memorable moments on set, and heard how “Insecure” taught everyone to dream even bigger.

Join HuffPost’s culture writers for a Twitter Spaces conversation about Sunday night’s episode and the season so far on Dec. 13 at 1 p.m. ET. Sign up to be notified when the Space begins here.

How has “Insecure” taught you to dream differently about your path in Hollywood?

I’ve been spoiled as a result of my experience working with Larry Wilmore, who was just so instrumental in making my voice clear and giving me the confidence that my story was worth telling. Then, of course, watching Prentice Penny as showrunner and being able to observe his dynamics and how much he respects writers and fosters relationships. He was just so incredibly gracious in making sure that I got to tell the story that I wanted to tell over five seasons, without ever feeling like there was an agenda on his side. When I think about an audience, I think about my friends and family and the people that this show was made for. To have that approval makes it clear that our stories are worthwhile and are marketable. That made me so proud and made me able to dream to tell more stories.

Prentice, who came from years of being the only person of color in writers rooms, wanted to create a pipeline for them to be promoted. Writers rooms would have diversity hires, and they would be capped at a certain level and wouldn’t be considered for other shows that weren’t written by people of color with people of color in mind.

For me, coming from the internet and having to really prove myself in a different medium, I had to prove that our stories were worth telling. I wanted other creatives that I respected to not have to go through that same process and to be able to have this opportunity where the door is open. If we only get a Season 1, you can say that you have this experience and get on to the next show.

Even with hiring directors for that very first season, we had several people who had never done television before, and a few who had experience. I remember considering Kevin Bray, who is the only director to direct an episode every season of our show, for the pilot because of the work that he had done on TBS, but it wasn’t considered HBO prestige work. So network execs were like, “Um, let’s think about other directors,” which ended up working in our favor because we got Melina Matsoukas, who is amazing. But then, after he directed an episode of Season 1, now he’s directing “Succession” and he’s just phenomenal. In cases like that where he can take a chance on someone and vouch for them, then they get to do something on a different level. He’s just been such a gift to our show. There have been so, there are countless instances like that on our show that we’re really proud of.

How has “Insecure” changed your life?

It’s definitely the thing that gave me my first big shot. Just being able to be on a show that was written by Black people, created by a Black person for nuanced Black characters, it shows what’s possible in the creative space. “Insecure” has been a phenomenal springboard. I’m hosting “Yearly Departed” later on this year. My book came out; I landed a comedy special on HBO. I got a chance to host “Ellen.” They’ve been amazing opportunities that have come because of the amazing reception of “Insecure,” so I’m forever grateful.

Tell us about a memorable moment on set.

I think the most memorable moments for me are when we were all together in those early seasons, and we would just clown each other. We really were a family: Jay coming in the hair and makeup trailer just to clown Issa and I or to have a musical breakout moment. Those are the memories that I will cherish and take with me.

I’ve always said I want to be a superhero. I want to tap into beautiful roles that really explore mother-daughter relations. I also just also want to bring humor and lightness into the world as well. I want to be a producer and a proponent for other people’s work and bring into the forefront new creatives.

Tell us about a memorable moment on set.

Wrapping this year was really special. Yvonne wrapped the night before Issa, and they shot this really beautiful scene together that Prentice was directing. He was doing an IG Story that day. His Story was just so poignant and so emotional and so everything that encapsulated our show and the love that we have for each other and the love we have for these characters. He turned the camera on himself at one point and started crying and said he wasn’t ready to let it go. We had one more take left with Issa and Yvonne. Then they came out of the room, and they were crying. Melina was there. It was just tears on tears on tears on tears. But it was so beautiful.

How has “Insecure” taught you to dream differently about your path in Hollywood?

It just feels like anything is possible. I walk around with this thought of “Well, why not?” Because why not a show about two Black girls based in LA that explores South LA in a way that’s never been explored on TV before? Why not have it be one of the biggest shows on this iconic network? Why not? No one can give a good enough answer as to why not for me to not be inspired to explore things and push envelopes and challenge previous conceptions of the way a show has to be made or a story has to be told or who has to be casted. Because we broke all of those conceptions with this show.

I haven’t really thought about the Lawrence chapter ending yet. I’m still in denial a little bit. I’m super excited for the world to get to see “Top Gun: Maverick.” I think it is absolutely beautiful and stunning and everything you want from a sequel. I’m very excited for the project I’m on now, “Somebody I Used to Know” with Alison Brie and Kiersey Clemons that Dave Franco is directing. I’m writing a book about my childhood imaginary friend, which has been a lot of fun, going into all these like childhood stories and talking about how they affected me in some way and how I carry them as lessons today.

How did “Insecure” change your life?

In probably every conceivable way. I moved to Los Angeles for the show. I don’t have any family in LA or California. The writers room became my family. I grew as a person, as a writer, as a creator by way of being on the show. Having started out as a staff writer and, in this final season, consulting producer, director and continuing with Kelli. So, I’m just grateful for the ride.

Tell me a memorable moment from being on set.

Oh my goodness. Five years’ worth of memorable moments. Honestly, I can’t even begin to answer that with any sort of modicum of truth without naming 3,000 moments. Ultimately, I think the common denominator is the people and being able to connect with other actors that I love and respect, directors that I admire and aspire to be like, and being able to tell stories that speak to the humanity of our people. I think the combination of those things — and I’m not being hyperbolic when I say this — every single day on set had that magic because of it.

Is there one “Insecure” character you wish you could build a bigger world around?

I’ve been doing so much press and literally everyone’s just like, More of you. I think it’s hard to say. I mean, comedically, I think Chad is so funny and such a dream to write for and see perform because of the rapid-fire way with which he delivers his lines. I want to know the world that man lives in, for sure.

How did “Insecure” teach you how to dream differently about what your path in Hollywood may look like?

I think for a lot of young creators of color — even without thinking — we are waiting for the industry to change and give us permission to tell our stories and look to them to tell us what stories to tell and how to tell them. There’s a lot of deference given to capital-H Hollywood. I think one of the things that Issa’s career has shown me is that we have the power to create the narratives and stories we want to tell. And, if given the opportunity, we have to be able to hold the elevator and even send it back down to bring more people up.

I think that’s one of the things that I’m consistently impressed by with Issa — not just what she’s created in “Insecure,” but in the careers she’s created from the show by supporting and uplifting diverse and marginalized voices. It’s evident when you look at the credits. You see a lot of women, and a lot of women of color, and reps from the LGBTQIA community and disabled people. I think that that has changed my relationship to Hollywood and understanding that I have power to be a part of the solution and not just wait for the industry to change. I can change, and thereby change the industry.

What has this character inspired you to do next?

I want to continue to write, portray, direct and tell stories in which the humanity of a plus-size Black woman isn’t a plot point. I think that’s the beauty of what Issa’s done with Kelli. Her role in the show is very specific. All the other characters are very utilitarian in that they serve the main character’s story, but she’s not a caricature. She’s a character. She’s also funny, and she’s sex-positive, and she’s not the butt of the joke. She’s in charge. I think more images of plus-size Black women and plus-size women being allowed to have stories and narratives that aren’t just there to justify her existence is so necessary.

That’s what’s exciting me about the work that I’m doing with Big Hattie Productions. It even influences the roles that I say yes to. When I put pen to paper, it really opens up a world of stories that I haven’t seen told and that are begging to be told. And so I’m excited to do it.

What about the role of Chad made you want to dive into the world of comedy?

So, I originally read for Lawrence. And didn’t get it, thank God, because it wasn’t for me. But then when they sent Chad, from the minute I read the lines, I was like, “Oh, I know that dude. I know Chad.” I might have been a little bit of Chad at one point in my life, but I knew that guy. Everybody knew a Chad, especially our people, Black people. We know Chad. Everybody know that dude. So, the opportunity to play him was just right up my alley.

When I had to go do the audition, I had two big auditions that day. And, thank God, I booked both of them. In the little bit of time I had, knocked it out, walked out, knew I had killed him. Everyone was screaming and laughing as I left.

The first days were stressful because I hadn’t done comedy. So, I wasn’t used to the pace and how it was done. And I really wanted to get it right. Keeping up with Chad, his speed of how he talked and getting used to the non sequitur ramblings of a madman who’s actually refreshingly honest, it was a bit scary. But as soon as we got on set and started chopping it up and started getting after it, it just felt like I was at home. I knew it was going to be something special because these guys were making me laugh.

Tell us about a memorable moment on set.

We were shooting at the start of the second season. We filmed two episodes that day. That day I had a breakdown. I was hurting. I felt inadequate. I felt small. I felt ugly. And I felt like I didn’t belong. And Jay Ellis and Prentice Penny took me off to the side, prayed with me, held me, talked to me through a dark, dark time. And then we put that thing on camera that you saw, which is hilarious. Everybody loved it.

But the fireworks going off in my head at that time: the lack of rest, the sleep but no rest. It was killing me. And those two men were warm, man. They were brothers. They were my brothers, they were my mothers, they were my fathers. They were everything I needed then. And that really stands out to me because they helped me until it didn’t hurt any more.

What does this show mean to you?

It’s a space to tell an honest, Black experience that doesn’t make us superheroes or supervillains. It just makes us human. It allows us to be human and fundamentally flawed and to explore the nuance of the human experience, honestly and hilariously. And that is special because we get to stand on strong shoulders that came before us and build on those shoulders and be even stronger for those that are going to stand on ours.

How has “Insecure” taught you to dream differently about your path in Hollywood?

When you first start out, like, oh, I want to be this famous actor. That went away after, like, five minutes. From then on, I just wanted to evolve and be the most believable and disappear into a character. I don’t care that people know my name. I care that they know the character’s name.

“Insecure” proved to me that I could do all the things that I wanted to do and pull out the other tools in my tool bag. And now people who are fans of “Insecure,” some are now watching me do some serious drama on “SEAL Team.” So, “Insecure” has really helped to open up that space and let me know that this house that I was in, that I had thought I had explored so much of and knew at least the nooks and crannies of all the rooms, it turns out I opened a door and I was just in the foyer of a bigger mansion. That’s what I’m exploring now.

What do you remember about the early days of the show?

I had originally auditioned for Lawrence and then Chad. I have a very specific memory of going into the callbacks for Chad, and it was the tiniest room. Issa, Melina Matsoukas, Prentice Penny and a few other execs were there. And there was an energy in the room; we were connected and I loved it. I had that callback for Chad, and it was amazing. I had worked here and there, but “Insecure” was big for me.

Tell us about a memorable moment on set.

Definitely the season finale of last season, when I’m running around with the girls. I really got to spend more time with Issa and Molly, the heart of the show. That whole episode was amazing. It’s the moments that surprise you; you’re just always finding new things where you’re just like, this is really fun and funny. It’s a rare thing where something really dope is happening in the moment, and I think that was just happening consistently, and it was really cool and special.

What did you learn from “Insecure” that you took to your other projects?

The funny thing is, I essentially went from being an indie filmmaker to pretty much only working on “Grown-ish” and “Insecure,” sprinkled with “Snowfall” and other real LA shows, which is cool for me ’cause I’m from LA. Both of those shows were a perfect spot for me to now be able to tell my own stories. It is both the how and the what: being able to mine your own life in a specific way that feels universal. And then there’s the how of it in terms of how to run a show and how to put it all together. All of that stuff was just incredibly helpful to experience.

What do you think the show captures so well about LA?

It shows the beauty of the parts of LA that never really got that treatment. LA is so sprawling, and it’s really segregated. “Insecure” came at that perfect time where Issa was able to show a city that people thought they knew and introduce them to new areas and businesses. That’s special because that’s literally generations of people who have lived in a city and think they know it, and then all of a sudden they see their own city and see it like this through the show’s eyes and it is a totally different thing.

How did “Insecure” change your life?

It was just an organic next chapter for my career. I wanted to work with Black creatives, and I was pretty unapologetic about it. My lawyer says that Black people are always depicted as either subhuman or superhuman; we have to either be demonized or criminalized, that hidden figure or someone who achieves something extraordinary. Meanwhile, mediocre white people get their stories told all the time. I really loved the messy gray area that Issa was bold enough to push for: We are human and we have our flaws; we have the potential to do so many things. I love the messiness of it; I love the hilarious moments of them just trying to figure things out. At the end of the day, sometimes they don’t get it right and sometimes it ends up way better than they expected, and just navigating that world and that experience. I got to play somebody from my hometown who is experiencing mental health issues. When I first got to LA and was pursuing acting, those characters weren’t around. He’s a regular-degular barber. There’s so many of our stories that I don’t think we get to see so hopefully it inspires more.

Tell us about a memorable moment on set.

During the uprisings, I was pretty depressed and frustrated and trying to heal, and there was nothing better than to have the support of my cast, not just because I work with them, but because they are Black and they uphold those same values and because they’re actually interested in being part of the work. So that’s one thing that was super heartwarming for me to see the donations, see them come out to the protests, to see folks actually speak out on my behalf. I felt protected and valued.

What does it mean to you to be on a show that pays homage to Black LA?

I’ve been out here almost 14 years, and I used to live in Ladera Heights. South LA has a very special place in my heart because I’ve built a community with folks that really cared about me and took care of me and brought me food when I was broke as hell. To see my hangout spots and neighborhoods showcased in that way is pretty special. I’ve done so much work in activism out here in LA, and “Insecure” is a revolutionary show without being about activism. We know our existence is resistance, right. And so showing us just being in South LA in an area that doesn’t usually get highlighted in TV and film is transformative, not only for storytelling, and what people see in broader America, but actually for the community. She invested in the community in real, entrepreneurial ways. I’m grateful to be a part of that; there’s so many things that could have built up my platform and given me more visibility, but to have something that actually blatantly expresses my same values in so many ways is something I couldn’t have ever predicted.

How did “Insecure” change your life?

I was a huge fan of the show, and of Issa’s work previous to that. Watching “Misadventures of Awkward Black Girl” as a theater grad student back in the day was so illuminating for me. It helped me realize I don’t have to just wait for some gatekeeper to give me the key. Issa’s disrupting the whole system and making her own thing about a girl that looks and feels like me. So just getting to be on that set was already huge.

It’s been a blessing as an actor because I’ve gotten to do things that I hadn’t done before. It’s been a blessing as a person, to work with people that I know I will work with again and I know are rooting for me and cheering for me as I go on, and I’m doing the same for them. And it’s been a blessing as a fan because I got to watch five seasons — or almost five seasons — of television on Sunday nights that I really enjoyed, and that I was able to look forward to seeing my community, my neighborhood — like, my literal neighborhood — and people who I know in real life on the screen every week. So it’s just been a humongous blessing, and I’m so grateful for it.

Tell me about a memorable moment on set.

I had not seen a set with so many Black people at every position, and never had I ever worked with so many Black executive producers, writers and decision-makers. And that was just mind-blowing. When we were discussing hair and makeup, I wasn’t having to explain the way my hair works. Just those little things. I miss it already. I really do. I think it’s a unicorn. The people who make that show happen, the actors, the crew, are just so dang good and so happy to be there, and the vibes are just right.

Was there something you learned from being on the show that you applied to another role or project?

One of the lessons I’ve learned, also as a fan of the show, and just watching what the show has done for the landscape of TV is that you can tell very specific, authentic stories about very specific groups of people. And there’s just no reason anymore that a studio executive can say, “Well, we just don’t know if other people will like it. We just don’t know if it’ll sell. We just don’t know if it’s relatable. How will it do internationally?” If you’re telling a good story, and you’re as authentic as you can be, it can be so specific and so relatable. Now, so many other networks are jumping on that bandwagon, and are like, “Oh, people do want to see young Black people? Oh, strange.” And so I think that’s a lesson for the industry in general, but also for my career in that, like, I can choose to do things that feel like me.

How did “Insecure” change your life?

It’s hard to quantify that, really. On a micro level, this show launched my career. This is a group of people who are not afraid to be bold in their casting choices, to cast who they believe are right for the role, not who has the biggest name at the moment. And for that, I’ll always be grateful. We refer to this show within the cast as the jump off, the platform from which so many careers have been launched. They conscientiously filled the room with Black and brown and multiethnic people. I think that really speaks to the unwavering commitment to the story they wanted to tell, rather than letting a studio or a network or any higher-ups take over any storytelling element.

How did “Insecure” change your life?

I was able to walk into more rooms with studio executives to pitch ideas for shows that I want to create. And that wouldn’t have happened without “Insecure.” Years prior to the show, I was dreaming of starting a production company. I was dreaming of producing my own show. I was dreaming of having meetings with high-level executives, and I’m able to do all of that. So “Insecure” has really been a key that was able to open some doors for me.

What does the show mean to you?

The show means walking into yourself, and in accepting yourself for who you are and being cool with it. It’s about falling in love with yourself. You have to love yourself in order to be there for other people and to be there for those around you. And I love Issa and Molly’s friendship, them trying to love themselves so they could be the best friends for each other. You know? You have to fall in love with yourself and accept who you are and where you are — and grow from there.

I’m curating a platform that will house short films from diverse filmmakers. Oftentimes you go to a film festival and you see some amazing short, and if they don’t get bought, they just disappear. It is also an opportunity for other filmmakers to create and collaborate with one another, and we’re providing resources for the filmmakers to learn the process. It’s a space that’s going to be funded by creators and supporters of films. My whole goal is to find a way to make short films profitable and create a launching pad for diverse filmmakers.

What do you remember about the process of getting the role and the early days of “Insecure”?

I remember auditioning with this scene where Frieda has this monologue about how highly educated Black women are less likely to get married, and it’s all in Issa’s head. Just from reading that, I knew there was nothing else like this show. It’s so smart, so funny. It’s honest. I booked it off of Skype and from then, I was so thrilled to see how it was received. With a lot of really smart, wonderful things, people don’t get it right away. But I feel like with “Insecure,” that wasn’t the case. People knew really early on how special it was.

Tell us a memorable moment from being on set.

Most of my stuff was with Issa and the kids, so it was always pretty fun. Just being able to play with them, and just letting the scenes be organic around who they were was really fun because you knew you were always gonna get genuine, fun kids stuff. I was kind of clumsy, and I would have to tell the kids a really serious thing, and then I’d run into these chimes that were in the corner. It was the scene at the end of Season 1, and we had the fundraising event at that fancy house, and I was telling the kids not to steal batteries. But I kept running into this set of wind chimes, so we had to keep doing it. I’m supposed to be the adult telling them what to do — and I can’t avoid the loud instruments on the wall.

What does the show mean to you?

As an actor, to have been a part of something that I believed in, from the beginning, and that became so loved was amazing. I just never knew if I’d have an opportunity like that in my career, to be a part of something that people really love and that people will stop you on the street and say they loved the show. It means so much to me. As an actor, you audition a lot; you put a lot of work out there, and a lot of times, nothing happens. And then an opportunity like “Insecure” comes along and you get that love back from the community of fans, and you see the impact. It makes you remember you can be a part of something that you believe in and that people also respond to and embrace. And that feels wonderful.

What does “Insecure” mean to you?

When people ask me about “Insecure,” I always say I was a small part of a BIG thing. I still remember shooting the pilot. We were at an office building in Leimert Park. I was there for the day. I had two scenes, no lines, and brought my own wardrobe. Set felt small and intimate that day. There were only about a couple dozen of us there, including Issa. Six months later when the show got picked up, I remember walking onto the Sony lot and seeing that exact same location recreated on a soundstage. We were filming Episode 2 of Season 1, and I’ll never forget looking across from Issa, seeing all the crew, the multitude of people and filmmakers now involved and thinking, “You did all of this. You created ALL of this. You created opportunity.”

I got to be surrounded by female writers, directors, producers, crew, cinematographers … and not only women, but women of color … and not only women of color, but many LGBTQ women of color. And the best part of all, is that even though I only played a small part, I still always felt like family.

How did “Insecure” change your life?

“Insecure” is one of the bravest, boldest, most provocative and funny shows on TV, so to be a part of the show was truly revelatory. I was, with every episode, thrilled and emboldened by the power of its messaging and the joy and love ingrained in the heart of its storylines. When I started my career, things were really different. I remember a different reality in an industry where cultural and gender diversity were not mandated or sought after in any real way. There has definitely been a change. I now see this every day I go to shoot: It was not really that long ago that I saw the first female director of photography on a shoot and certainly, until recently, you could count on one hand the number of women in any camera department at all.

Tell us about a memorable moment on set.

One of my most memorable moments on “Insecure” was when I drove up to the trailers on the lot. They were all grouped together like a family outing, and that’s when I realized that I was on a show where all were embraced. I clearly remember walking to my trailer, and looking around because something felt so different. And, then, it hit me with such joy that this was by far the most gender-diverse and culturally diverse crew that I’d ever worked with. It was electrifying. I stood in awe. I was so excited to be there. A moment I will not forget.

What has this character inspired you to do next? What do you hope to do next?

In playing the character of Joanne on “Insecure,” I was definitely inspired to up my game, be more fierce and hold fast to my courage. “Insecure” inspired me to always remember to flow and glow when shooting. As I currently shoot my next TV series this fall, I take inspiration from the creative boldness and freedom of so many of the actors on “Insecure,” led by the visionary Issa Rae.

How did “Insecure” change your life?

I literally quit my day job saying, “I’m on HBO!” “Insecure” not only gave me my first real part on a TV show, but allowed me to try new things and develop a character. I also got to be along for the ride and witness the behind the scenes of how it all worked and morphed from the table read, to set, to screen. In the first season, the magic and vulnerability was palpable and I think everyone felt we were making something new and special. Plus, I love when random people yell, “OMG! You’re the annoying girl from Issa’s office!” I’m like, yep, that’s me.

Tell us about a memorable moment on set.

When we rode on the 10 Freeway in a loop on a school bus with our We Got Y’All kids screaming; our director Melina coaching the kids laughing loudly over the traffic, trying to get that beach day bus scene in Season 1, Episode 3. That was a hilarious and long day.

What has this character inspired you to do next?

I’d like to think Kitty is the original Karen. The well-meaning, entitled know-it-all who thinks she’s woke but is pretty clueless. Hopefully my character opened the door for more unlikable Karens and the hard, real stories they bring up where a conversation can start and hopefully lead to more understanding and change. I’m not afraid to play someone the audience loves to hate. I like uncomfortable conversations.

Is there a recent role that came for you based on your role on “Insecure”?

I’m lucky to lend my voice to four unlikable characters in “We Stay Looking” podcast, a spinoff from one of the faux TV shows Issa watches on “Insecure.” All of my voices have a tone of Kitty’s unabashed tone deafness, and it was fun to stretch and play with her again using just my voice.

Tell me about a memorable moment on set.

I showed up to set, and it was incredible to have remembered the first episode of shooting “Awkward Black Girl,” to being on an HBO set, surrounded by women of color that were in charge, and being in my trailer and getting my hair and makeup done and having wardrobe. It was such an emotional moment for me because it showed such growth and perseverance.

Another moment is when we were shooting the beach scene in Season 1. I was standing outside of the bus, watching the kids come down, and it all hit me at once, and I got really emotional, and tears started falling down my cheeks. One of the little girls looked up to me and was like, “Are you crying?” I was like, “No, no, it’s the beach, the wind, the air is, like, hitting my contacts!” I just lied. I’m looking around and there’s a crane and there’s the cinematographers and there’s video village, all the producers are there, Issa, the whole We Got Y’all family, and it just hit me. I remember filming in Issa’s dad’s doctor’s office in Inglewood with two other people, and now this is the actual show.

How has “Insecure” taught you to dream differently about your path in Hollywood?

Issa just inspired me to write more and write truer to my voice and my experiences. That’s what I supercharged myself into doing, and in that sense, that’s really where the premise and the seed of “Definition Please” came from. I’m gonna write about this girl who’s a former spelling bee champion and might not be the stereotype of what an Indian American character plays in the media. And I want to make it real and true for other people.

How did “Insecure” change your life?

It changed my life in so many ways. I am so grateful to be part of something that moved the needle for the culture. It introduced me to an audience, completed my goal to work with HBO, my daughter’s parents are both a part of the show, LOL, and elevated me all around. The show means EVERYTHING to me. The representation of us on an HBO series is golden. All walks of life. Us being people. The respect this show gets is more than deserved.

Tell us about a memorable moment on set.

Season 2, Episode 7. Derek’s birthday dinner. Between takes, the cast was at the table singing Donell Jones, Musiq, all types of Black classics, and it filled me with so much joy.

What has this character inspired you to do next? What do you hope to do next?

All my roles after have been because of “Insecure.” “Good Trouble,” “Games People Play,” guest-starring roles on shows and independent films. Meetings are easier to get, too. I’m just extremely grateful. I just want to do quality work with my people! Keep representing us in a real way. But I want to eventually get into some action and thrillers. Mix some things up. Put my athletic ability to use.

How did “Insecure” change your life?

It’s been a wonderful experience. I wanted to be on the show before it was a show because I was a fan of Issa and her web series. It just felt like it was going to be something important and big. And I was right. I love being included in that universe. Showrunner Prentice Penny, and Melina Matsoukas, the pilot director, they’ve just been very aggressively focused on making sure there’s representation not only in front of the camera, but behind the camera. I’ve seen people come in and get their first job and be promoted and elevated through the ranks in their own departments. And I think that’s just an amazing thing.

What does the show mean to you?

What I love about it is — even from the title — it puts us in a different light and shows us we can be messy and vulnerable, and have some struggles, and we should celebrate that. I think the comedy and the stories are very smart, and how it’s not preachy or heavy-handed. I think that’s a real testament to the writing, all the layers that are built in. It’s also a celebration of LA in a positive way. It’s great to see people out in Los Angeles, loving life, celebrating life in a way that seems realistic.

Tell me a memorable moment from being on set.

What’s great about Season 5 for my character, Torian, is we see a little bit more personality and backstory. The joke I made on set was like, “Oh, I finally get to smile.” I always have a lot of love for each of the writers on the show. I tested for Lawrence, and then came back and auditioned for Chad. So I’ve had several auditions to get me in the show, and it just didn’t work out. So then a phone call comes in and says, “Here’s a role. Do you want it?” There was nothing to read; they didn’t have it written yet. They just had a description: Torian, a lawyer at a new law firm. I believe that what is for you is for you, and so when it comes around, then that’s your job.

What has this character inspired you to do next?

The show really made me narrow in and appreciate projects that do more than just entertain. It feels good to be part of something that’s impactful and has an influence on all the culture. Issa, Prentice and the crew have basically laid the blueprint as to what you do when you get your foot in the door: You hold it open as wide as you can and let as many people through it as you can.

Tell me about your reflections on this journey from “Awkward Black Girl” to “Insecure.”

It’s heavy. It’s bittersweet. First of all, I feel grateful to be part of this journey. How beautiful that my introduction to the entertainment world professionally gets to be on an HBO show about my neighborhood. We’ve never seen South LA presented this way on television. Whenever we saw South LA before … We’ve never seen South LA represented in a way where it’s a beautiful place with lots of character and lots of characters, including people like Thug Yoda who, yes, has gang affiliations, but he’s just a dad. He’s really just a dad doing his best, living his life. I’m grateful to have played this part.

How did “Insecure” change your life?

I remember that at the time I had only done “Awkward Black Girl” and I did one commercial. That was cool. I was taking acting classes to prepare for whatever opportunity comes up. Then, sure enough, the opportunity just came up to be in “Insecure.” I read for another role at first for the pilot back in 2015. When that didn’t work out, Issa hit me up and was like, just know that you’ll be at the front of my mind. January 2016 came around and she was like, I have a perfect role for you: Thug Yoda. She sent me the scene. I thought it was hilarious. I auditioned. I booked it. Even in October 2016, when it first debuted, I still didn’t have an agent or representation at all.

When people saw this character, first of all, no one knew that it was also the Baby Voice Darius from “Awkward Black Girl,” it was just, this dude is funny. He’s changing all these C words to B words. That’s hilarious. This is great. That’s how I got my manager, who reached out through Jay Ellis, then I got representation. This role literally springboarded me into the career that I have today. I don’t think I would be here if it weren’t for this role and if it weren’t for Issa.

What does the show mean to you?

“Insecure” has already made history and to be a part of a project that changes how Hollywood as a whole perceives talent and creatives of color is humbling and truly inspiring. I value every experience on set, but working on this set pulled on heartstrings. You are invested on a different level when you know that what you are creating is widening that door and hopefully making it easier for other artists who look like you to walk through. I was aware that “Insecure” was the first on-set experience for some of the cast and crew, and it was emotional because you’re always thinking, are we all aware of how rare and beautiful this is? And you think maybe this moment changes the “rarity” and maybe one day THIS becomes common for my people.

Tell us about a memorable moment on set.

Entering the hair and makeup trailer that was full of African American hairstylists. I get chills thinking about it. To arrive on set and not have to have your own hair and makeup products stashed in your trailer because you know they can do your hair and makeup, it’s almost a religious experience. I get emotional because as an actor you can just relax and find your quiet place so that you can actually do your job and not be worried about having heat damage when you wrap. I’ve been acting 11 years, and this is the ONLY set that I didn’t have to consider my hair and makeup every day.

Was there something you learned from being on the show that you applied to another role or project?

Every project teaches you something; sometimes you learn what to do and other times you learn what not to do. This show freed me up to speak to the authenticity of the Black experience on other sets. For instance, don’t set a full plate of macaroni and cheese in front of my character because in the African-American community mac and cheese is not an entree; it’s a side dish. This show gave me the authenticity that we didn’t see before on television, and I’ll never give that back.

How did “Insecure” change your life?

Playing Trina was one of the most liberating things I’ve done as an actor. Comedy takes a brilliant sense of timing to nail it and that really intimidated me. “Insecure” set the stage for me to challenge myself, and ultimately, I got to thrive in doing so. I’ve been an Issa Rae fan since “Awkward Black Girl,” and I’ve gotten to see her take nuggets from that web series and create a show that honors the kaleidoscopic experience of Black millennials like no other! And, as an artist, I feel privileged to have been a part of that world.

Tell us about a memorable moment on set.

There are moments where we could barely make it through a take because we couldn’t stop laughing, and ones where even I had to judge Trina’s absurdity. But the one I cherish deeply, was my first day on set after “Bad Hair” had come out. I walked in after Issa, Yvonne, Natasha and Amanda were wrapping a scene, and they all turned to me and gave me such huge congratulations and cheers. I felt so seen and supported. I’m smiling just thinking about it.

Was there something you learned from being on the show that you applied to another role or project?

I’ve learned a lightheartedness that I’ll carry with me on every set. There’s a sense of play that I think I forgot in the pursuit of accomplishing my grandiose dreams. I grabbed a hold of that again, and I ain’t ever letting it go.

Tell us about a memorable moment on set.

The whole experience of me being on the show was a memorable moment, but if I had to choose one specific one, it was the way everybody who was on set was treating me, and how they were treating me like I was family and how they just had good vibes.

What has this role inspired you to do next?

The character inspired me to want to get more roles and inspired me to want to just do it more and get more experience of different sets. It also inspired me to do more comedy because I made people laugh, and I’ve seen people have joy in their face from my performances.

How has “Insecure” taught you to dream differently about your path in Hollywood?

It made me dream bigger because it made me want to be on the big screen, and it made me want to be on more TV shows, and it also made me want to inspire other young actors to want to do it too.

How has “Insecure” changed your life?

Oh, wow. I’m much cooler to my niece. One of the stories that I like to tell about my first episode was just watching Issa go from the makeup trailer to behind the camera later in the day when she was done doing her shots and just running things. And so I think it’s impacted me much the way it has the industry, which is this boom of Black creatives who are in front of and behind the camera and really, truly owning stories. And so seeing that up close and personal is both a personal and professional inspiration. And so I think that when you’re navigating the waters of the industry, especially as an artist of color, being able to look to real-world examples of “It can be done, just keep going.” It’s always impactful.

Tell us a memorable moment from being on set.

I had a lot of fun when Regina King directed. I’m a fan of her work and so it was really nice to have the opportunity to be directed by her. I love being directed by actors. There’s a shorthand that we have that certainly can be learned by directors who were not actors, but it’s kind of upfront and present.

How has “Insecure” taught you to dream differently about your path in Hollywood?

That’s the Issa effect. It is when you see people boldly telling their own stories unapologetically. She’s done interviews about how there were mandates in the beginning from TV execs, and that as the show grew and became more popular, her imprint grew so much that she could speak up even more. She shifted the show to what she ultimately always wanted it to be. Real-world examples like that in the industry are powerful.

How has “Insecure” changed your life?

It’s been great. Every time I go to the set, you see people of color and women in these positions of leadership and power and creativity. I’m probably one of the slightly older members of the cast. The struggles that I’ve had, being a professional actor, it’s just great to see people of color in decision-making positions. It’s been so positive to see that there is a generation coming up that are very clear on the message they want to send.

We live in a very different time now. I’m a child of the civil rights movements, but still, we live in a very different time after 2020 and the murder of George Floyd and a global pandemic. To see the messages that younger people of color, LGBTQ+ people, want to say, the stories and the narratives that they want to form, I find that really exciting. I find myself sometimes sitting back and learning a lot about what’s happening now with our brothers and sisters and I’m very proud of them.

Tell me one of the most memorable moments from being on set.

When Yvonne and I negotiated how she’s accepting me again. I didn’t realize how touching that was. I did cheat on my wife in earlier seasons. We’ve reconciled, my wife and I, but Yvonne Orji, who plays my daughter, has a hard time with it, even though it’s passed. She’s been having a hard time with reconciling her father’s infidelity.

That gesture of bringing out this pie to give to me, and looking at me in a way that said, “I’ve had a hard time with this, this is difficult, but you are my father. And you and Mom, I don’t know how you did it, because I wouldn’t have done it, I wouldn’t have reconciled with your butt afterwards,” but that was very touching, and the way Yvonne played it was just simple. Oh, I was so touched. That was so sentimental.

Also, I got to work with Kerry Washington. I was like a groupie. I was like a fan. I was like, “Oh my God! It’s Kerry Washington! Can you believe it?” She was a dear. Wow, to watch her work, she’s funny and she’s talented and she’s a terrific director, but just the fact that I got to work with her, for me, was yay!

How has “Insecure” taught you to dream differently about your path in Hollywood?

I want Black fathers and Black men that I portray from here on in, not that I haven’t before, but they should have grace and dignity and love and support, because that’s what my father did for us. That’s how our family survived. God knows mothers and sisters are the backbone of the family, but to see fathers actively be a positive force in their children’s lives, particularly brown and Black families, and I want to see that. I want to be a part of portraying fathers who helped get their children to the next level, who sacrificed everything to get their kids into school and to give them the opportunities that they didn’t have. That is something I want, because I think that’s important. I think somehow Black fathers have been marginalized in some way. Their contribution to the family has been sort of marginalized or looked over or lessened. But I really want to do roles that exemplify the importance of how men, how Black men, how Black fathers are integral in their family’s lives and their children’s lives. That would make me very, very proud.

How did “Insecure” change your life?

Honestly, I started off as a fan of the show. I remember the show aired back on Oct. 9, on my birthday, in 2016. As me and my wife were watching it, I remember looking over to her, and I said, “Yo, I’m going to be on this show.” And I end up being casted the next season. That’s how I knew being on this show was going to be a huge impact, not only to the culture, but to my life as well. It’s opened so many doors for me, honestly.

What does the show mean to you?

I love the show just because it shows Black people, predominantly Black women, just being themselves. I know we tend to like shows about the drugs, and the money, and the gangs, But that’s not every Black person’s life. I think Issa, Molly and Lawrence show you typical Black people moving through life, typical Black millennials who are trying to figure things out. I think “Insecure” has been so big just because it’s relatable to a lot of us.

Is there a role that’s come to you based on your role in “Insecure”?

Yeah, I actually did a film on Prime Video called “Perfectly Single.” I did that through “Insecure.” Some pilots did come about, unfortunately, they didn’t pan out the way I wanted to. But as far as the connections that I made, I’m really with the whole cast. And I say this wholeheartedly, it’s like being on set with your relatives. It’s like being on set with your cousins, and your aunts — it’s just a really feel-good environment. The end is bittersweet, but the culmination of Seasons 1 through 4 is really going to play out in Season 5, and it’s been a great ride, for real.

How has “Insecure” taught you to dream differently about your path in Hollywood?

Just to be authentic. I can’t give them enough praise. I love the fact that the “Insecure” cast and crew just embraced themselves. It taught me it’s OK to walk into these rooms, and say, “This is what I’m going to give you.” I’m not going to give some super over-the-top version, some exploited version of myself. I want to give you me, the authentic me. It’s so real, and I’m just blessed to be a part of it.

What does “Insecure” mean to you?

First of all, it has given me street cred to be affiliated with such a cool show. It means that I have become part of history. The show has broken all kinds of barriers and opened doors for many new creatives to get a start. We’ll be talking about this show for many years to come and the fact that I played some small part as Molly’s mom makes me very proud.

Tell us about one of the most memorable moments from being on set.

The most memorable moments have all occurred between takes or between setups. It is when all the actors are sitting together laughing and talking, cracking jokes, teasing and getting to know each other, bonding. That is when the real magic happens.

You’ve worked on a ton of TV series. How has working on “Insecure” felt different than other shows?

On every single show I have worked on, the entire team, top to bottom, in front of and behind the camera: They’re all working hard to create the very best storytelling for their audience. It includes long hours and sometimes tough conditions, but everybody is pulling together like a team. “Insecure” is no different in that regard. The only difference in this case is that the vast majority of the “Insecure” team are people of color and young creatives that haven’t previously had the opportunity to show what is possible. The thing that you don’t notice while it’s happening is that there is this easy shorthand that occurs. I will note that the ONE big thing on a show like “Insecure” is they honor and respect you as an elder. I am “Miss Scotty.”

How has “Insecure” taught you to dream differently about your path in Hollywood?

In a 40-year career, most of my dreams are in the rearview mirror now. I only dreamed of being a “working actress” because I didn’t see examples of more possibilities. As I look ahead, I am enjoying the collective dream of the next generation. Once upon a time, a woman of color at my age had nothing to look forward to. Now we do, because a show like “Insecure” teaches us that there are so many stories to be told, and ALL is possible.

How has “Insecure” changed your life?

This was really my first foray into television and filmmaking. I had done videos and commercials and for many years, was looking for something that spoke to me in the narrative space. I hadn’t really found anything. I would always get scripts that are musicals, or things that weren’t really in line with my taste in the narrative space. One of my agents sent me the pilot script for “Insecure.” I read the script and it just spoke to me in every way. I related to Issa Dee as a character, Issa Rae as a professional Black woman having to navigate through all these different spaces and speak all these different languages — and do it in her own way. It was something I was doing in my professional career as well. I always like using comedy as a way to survive, and it spoke to me. I knew I could really bring the story to life. I met Issa and we spoke the same language; it was so nice to not be othered for once and to really have a real partner and collaborator in Issa and Prentice. We made this beautiful piece of art that became the pilot. It was magic, and it got picked up very quickly. Then, we have this show that and I don’t think any of us knew it would have the kind of impact it has culturally. Having fans’ reactions in real time on Black Twitter every week is a really satisfying moment. To see that and then be able to take that with me, it was life changing.

Tell me a memorable moment from being on set.

The gender parity and also the diversity. There’s not many shows that are so diverse. We all come from different backgrounds and we want to represent a world in which it exists and to be able to create stories with people whose stories they actually are. Everything is authentic, from writing to the locations. What is memorable to me forever is, like, me and Deniese Davis, who’s another producer on the show, literally riding around in my car on weekends after we would shoot and knocking on doors so that we could find locations to shoot in those neighborhoods that were represented. Nothing was ever falsified. I remember in the first season, they’d be like, “Oh, well, we can fake Pasadena for Inglewood.” We’re like, “That’s not who we are. That’s not what we’re doing. We want to shoot in those communities. We want to represent them honestly and truly.” The dedication to authenticity is the most memorable part of it, and something I will take with me to every project. I feel like there’s no other way, really, to create real representation.

Is there one character on “Insecure” that you wish you could build a bigger world around or one that you wish could get a spinoff?

Absolutely. Can Kelli have her own episode?! I would love to just live with Kelli and know how she exists in the world, and see what the ins and outs of her days include. They never granted my wish, but I think that we’ll always be wondering that. Natasha is an incredible actress and writer, and she directed an episode of this season too. Her character has always been my favorite, her and Thug Yoda. I was like, “Can we have a moment where they go on a date and we’re with them?!” That would be my dream.

What lessons have you learned working on this show?

The collaboration is incredible and respectful and also we push each other to be better. I would love to have that kind of relationship with other creatives that I’m working with. Then, being able to foster such a diverse community on set I really feel is important to take with me for every project. Then, that dedication to authenticity is something I take with me to every project and that fight to be able to represent these stories authentically is really important.

How has “Insecure” taught you how to dream differently about your path in Hollywood?

The biggest lesson it’s taught me is to work on things that really speak to you and that feel true to who you are as a person. If those stories and opportunities don’t exist, you can create them yourself. Now that you know people see the real value in our stories, they’ll get made.

What’s next for you beyond Insecure?

I have three television projects that I’m directing and producing right now within the next year, and I’ve also started a production company and agency that represents other creatives of color in the photography space, directing space, film and TV, music videos and commercials. I’m really just trying to give back what I didn’t have, the guidance through all the different kinds of genres of media, and support new voices that are wanting to create. I’ll continue to do my directing and in TV and film and also a lot of producing for other projects.

How is working on “Insecure” different from other projects that you’ve worked on in the past?

The beautiful thing about HBO is they don’t care about offending people, so it was the perfect place for Issa to continue her style. Part of her style was, “If I’m going to make a show about where I’m from, then I’m going to shoot it where I’m from.”

She almost flipped the litigious circumstances of filmmaking, or the nature of the business now, on its head. She’s like, “If I’m going to use Ladera Heights, I’m shooting Ladera Heights.” We’re going down there, and most importantly, we are spending the money that we have for production on that community because we are using that community in our storytelling. Time and time again, she did that. That was really hard for me to digest at first because I was like, “This is going to make it so much harder.”

But, at the end of the day, there was appreciation for her, and there was a global appreciation for her from HBO. HBO got this byproduct of good faith. Then you can watch the show and you know that you’re looking at this exotic new world. I just think that’s what she does that’s so tremendous and that keeps growing. I just watch her maturing and expanding, and I think it’s just limitless.

Tell us a memorable moment from being on set.

When she goes to Daniel’s house and he ejaculates in her face. Not that moment, but when we shot the white girl saying she wanted to hear some other music in the back of the car when she’s getting in the Uber, and the dude said, “Issa something ride.” Something about the way that final scene shot kind of really rang so true for me. It was so funny, and the whole crew, everyone was gathered. When people gather around the monitor, you know you’ve got gold. People were just cracking up. That was a really special moment where everyone was firing on all cylinders and everyone was contributing whether it be the location, the production design, storytelling, the actors, everything, the music, all of it came together to be a quintessential pure moment.

How has “Insecure” taught you to dream differently about your path in Hollywood?

I think it really reengaged me in what was happening out there and then therefore made me see connections and stories or ideas I wanted to tell. Also, you have a quiver of aptitude or you have your quiver of history or what you studied to be able to do what you do, whatever your vocation is. Then I suddenly saw that I could apply some of my old referential stuff to this new genre, or this new group of people, and they would have something absolutely new that they never thought of before.

So that got my creative juices flowing again. It kind of rejuvenated me; it made me have to keep up and also get me from being cynical. One of the most important things that’s happened recently is the moment in “Ted Lasso,” where he says his father said, “Be curious. Don’t be judgmental.” It hit me because I have to stay curious, and I can’t be supercilious when I’m looking at young people and go, “Oh, I’ve seen that before. That’s just a rehash of blah, blah, blah.” I have to think about why it’s happening now and all of that stuff and then be curious about it.

How did you first become involved with the show?

I first heard about the show during Season 1. My friend Deniese Davis had been working on “Awkward Black Girl.” And then I sort of heard that they got an HBO deal. And I watched the show, not even realizing I had friends working on it. And just like, oh my God, “Broken Pussy” — I just became a huge fan.

I just saw a huge opportunity because between Melina Matsoukas and it being HBO, where you don’t have to make comedy bright and sort of flat, and the way music plays a role and how important music is to Issa, I just felt like there was this crossroads in visual culture that I could imagine the show slipping into. But mostly, I just became a fan pretty instantly. When the job became available the next season, I just went in and was very honest with what I would want to do and see because I felt pretty strongly about what I would want to do and see. And somehow, I got the job.

You’ve also directed a few episodes. How did you get into directing?

I’m a DP, and I love my life as a DP, but there are other muscles that you get to flex when you get to direct. I wanted to try using these muscles and I know I can do the show justice; I know I can do what needs to be done because I supported so many directors coming through. It was a real honor for me for them to just trust me like that.

Tell me about a memorable moment on set.

The most recent one was when we were completing Season 5. We were literally shooting a night scene as the sun was coming up. I just kept having to throw up more and more black solid cloth around the scene to block out the daylight so that we could finish the scene and finish the season and say goodbye to these characters. It was really epic, and it really was sort of emblematic of this feeling of like, you don’t want it to end. But it’s natural that it ends. The sun’s gotta come up.

How did “Insecure” help you to think differently about what your career could look like?

I never thought that I would be in a dramedy TV space. I come from a documentary background, and everything I’ve shot is pretty heavy and pretty dark vy. “Insecure” kind of opened up this world to me where — and this is one of the beautiful things about the show — yes, it’s about a group of Black friends in Los Angeles. But it’s also about, and Prentice always says this, and I love it, and I quoted him before, but he says, it’s about the beauty, not the burden. And the writing comes from that place, and it makes it human, and it makes it sometimes funny and sometimes sad. And I found how easily or how comfortably I fit into that place. I feel open to being able to explore different genres that I didn’t expect I would when I was coming up as a DP, and I feel like it’s just opened my eyes to how wonderfully culturally relevant our work can be. And it’s not just to other artists, and not just to a small group of people. It can really be relevant to the culture. And, as a DP, that’s just like the most beautiful possible thing.

Is there one character that you wish you could build a bigger world around?

It would be fascinating to see if we followed Kelli off into her own world. Does she ever get any more grounded, or does she kind of stay in that place? I would also still want to see the other members of the ensemble come in and out of her life.

So for me, it’s so hard, because it’s like family, it really is, the way that I feel about the characters. I am drawn to the alchemy of them. It is such a great word, because it is to me, what you see on-screen, really is reflected. It starts with that alchemy that Issa and Prentice created. I want a balance of personalities, and I think they did that so well, and it is reflected on-screen.

What have you learned working on the set of “Insecure” that you are taking with you to your future plans?

For me, how you approach the process of hiring your team, both my team of executives within Loud Sis Productions, and also if I am running a show. There is just an ability to be nimble that I really admired in Prentice’s process as showrunner. And Issa, when you have, again, such an undeniable voice and talent and ability but still have the ability to listen and create this magic. It means not letting your ego be the filter but letting actually your instinct and your voice and your creativity be the filter.

The analogy that I use a lot is, we’re going to take a road trip as a room. So we know we are driving from LA to New York as a writers room, but if someone wants to stop in Vegas along the way, I want to be open to stopping by a casino. Or I want to stop and get some barbecue in Kansas City. I am basically speaking to how you can invite others into that process. You know where you want to go, and what story you want to tell, but how you would invite others to contribute, to get in the car with you, and actively contribute to the process of going across the country.

How has “Insecure” taught you to dream differently about your path in Hollywood?

Part of the beauty of “Insecure” is that I am still friends with the people I worked with on those three seasons where I was writing for the show. I also feel even more empowered to tell the stories that I want to tell. As a writer and as someone who got to be in that atmosphere, you go on this journey of recognizing what you are capable of in a more complete way. It helps to remind me individually of what I am capable of and reminds me of the collective of my family and tribe. And that’s really powerful.

What does “Insecure” mean to you?

Self-love. The power of your voice. Prior to being hired on “Insecure,” I’d grown insecure about my own creative voice. I felt marginalized and alone as a Black television director working with predominantly white crews and showrunners.

Tell us about a memorable moment on set.

It was the very first scene I directed. A sex scene — overhead shot — where Daniel was going down on Issa. In my mind, I was being respectful, shooting it in a way where you didn’t really see anything. Issa took me to the side and said, “We need to see it.” I was like “Oh! Got it.” She wanted things to feel and look as authentic as possible.

What’s a lesson you took away from working on the show?

I learned that Black comedies can be aspirational, cinematic and beautiful. It’s not just about the jokes; it’s about the character journey.

How has “Insecure” taught you to dream differently about your path in Hollywood?

It’s a family first. I just did a pilot earlier this year with Phil Augusta Jackson, a writer and executive producer on “Insecure,” for his NBC series “The Grand Crew.” That’s an example of what it means to be a part of the “Insecure” family. Everybody looks out for each other. Since my first episode on the show [Season 3, Episode 3], I’ve directed five pilots. I know for a fact that my climb in the industry is a direct result of Issa and showrunner Prentice Penny putting my name out there.

You went from assistant to writer. How did that happen?

I already knew Issa, and she already believed in me and felt that I was capable. I was coming in as an assistant, but I was coming in with the knowledge that I wanted to write someday and Prentice was kind enough, incredible enough to welcome me and just kind of take Issa’s word for it when she said, “Syreeta’s great.” I came on as Prentice’s assistant and writer’s PA for the first season. I just took that year to learn and Prentice was so great about that. I went with Prentice everywhere that year as an assistant. I went to every meeting, and I just observed and I watched, I took notes for him, and I got to really see the production firsthand. I used that time to just connect and literally every day was just about soaking it in. And it was such an incredible year and I felt so inspired and personally challenged as a writer.

Tell us about a memorable moment from being on set.

I’m from South Central LA. I went to public schools. I went to community college. That’s my background. And being in writers rooms with people who went to Harvard or people who wrote on “SNL” or just wrote for shows that I just wouldn’t even imagine ever being in the same space with that person. Initially, I was aspiring to make my pitches or my jokes be like theirs; that was my original kind of thing that I was telling myself.

And Jen Regan, our script coordinator in Season 1, was like, “You’re perfect for this show. And you’re going to be perfect for this show because you know this world better than anybody here.” And she’s like, “This show is in your city. It is about Black women who are your age. This is a voice that other people are trying to write. This is who you are. It’s going to be natural for you.” It was a reminder that I don’t have to try to tell anybody else’s story. I don’t have to try to speak from anybody else’s POV. I can speak from mine. I can do this right from where I am. And just that lightbulb was a game-changer for me.

Is there one character you wish you could build a bigger world around or get a spinoff from?

I love Molly’s family so much that I would love to see a show that is Sunday dinners at Molly’s family’s house. And I want to follow her brothers and see what dating and living in LA is like for them. And Curtis and his stripper wife. And how they navigate that. And what kind of parents they are and see Molly be the auntie that pops in here and there. I would be interested in that show.

What does “Insecure” mean to you?

I wrote for “Awkward Black Girl” too, and I remember watching that first episode before I was hired and feeling chills. I am the person who says goodbye to someone and walks the same direction or drives the same direction. It felt so like me. What does this show mean to me? I mean, it just validates the experience of a Black girl who likes hip-hop and rap and American Black culture and also can live in the awkward, “I don’t fit in here” space. Both of those experiences can exist in one person and they exist in me. What it means to me is everything, the ability to see yourself reflected in these characters. It’s validating. What “Insecure” means is the permission to contain multitudes. I feel like that is what it is. It’s the permission to be exactly who you are as a Black woman walking through the world. You don’t have to be anyone else’s version but your own.

What is something you’re taking away from working behind the scenes of this show that you want to be sure to take with you?

I think I would say trust the youth. I’m a millennial and millennials are old now. I think of the beautiful relationship between Prentice and Issa. When he started, he was just entering his 40s and she obviously was a little older than her character, who was about 29. That’s not that big a difference, but younger people move a little differently. I think it is a fear instinct for people to say like this young person doesn’t do it “how it’s supposed to be done,” and therefore they’re wrong. I have so many writers that I mentor and a lot of them are younger than me and they will say that they’ve done things at work where I’m like, whoa, I would’ve never done that or spoken to my boss that way. There is a changing tide and with youth comes fresh, new thinking. For me, I am so looking forward to developing projects from people who are young and people who haven’t haven’t been in the system for so long.

Tell me a memorable moment from being on set.

I really loved directing Episode 7 of Season 5. Yvonne came up and started filming me while I was directing. I was like, “This is amazing. Like, wow, two Nigerian women on this set.” That’s memorable every single day. Anytime I got to sit next to Melina and listen to how her mind thinks and how she makes decisions, it was always so beautiful.

In the Season 1 finale, where Issa and Molly are driving back from Malibu to LA, and she’s trying to get to Lawrence, they’re driving on the PCH. We couldn’t shut [the PCH] down even at night. They put the car on a process or dummy trailer, but it sits in a parking lot and it just wiggles as if it’s driving. Then, they put this helicopter on a stick above the car that spins around and shines a light every five seconds — and that mimics the street lights. Then, there was a guy standing beside the car with ropes in his hands, like ropes at the gym that you practice with, that had lights on the end. That’s the mimicry of a car driving by. I remember seeing this, I filmed this shot, and I was like, “This is movie magic!” To see our crew come together to brainstorm to make shit real, that is like when you’re like, “Oh, I’m making movies.” That’s what feels so magical about this.

How did you join the writers room?

I had been working on “Ballers,” and HBO just recommended me to Prentice and Issa, and they had a bunch of turnover between Season 3 and 4. I think they had lost all their men. [Laughs] They were looking for new writers, and I met with Prentice and Issa, and it felt like a really good fit. I’m super grateful to get to just jump in, and it was nice. The writers that came in that season — it was me, Grace, Phil and Eli — we were lucky to come into this hit show that was already this well-oiled machine.

What will you miss most about working with this group of writers?

I’m just gonna miss working with everybody. Every single second was a party. But it was always just so rewarding, when we were banging our heads against a story. But there’s something about that camaraderie and that magic of going to work with your friends.

It was just a very beautiful and sadly rare space, even in today’s industry that is making a lot of strides. I mean, I was the only Asian American in the room, but I never felt that. In other rooms, I felt that. During Season 4, when Andrew was a big storyline, like there wasn’t that weird tiptoeing around issues. We could just just speak about them, and I never felt tokenized or marginalized or fetishized or anything, which is what happens when a room is just organically diverse, and full of people who are used to being empathetic to other people’s experiences.

What are some lessons you learned from working on the show?

So much of the environment they created is just that they are wonderful, respectful, nurturing, kind, hilarious people. Prentice, especially, kind of came up in a different world that was significantly less diverse. There’s this eye toward really nurturing each other and taking care of each other when you’re a person of color in this industry. And if you’re a person of color in this industry, and you are at all successful, you have shoveled so much shit. You have put up with so much bullshit. They created this environment that really just felt like a celebration.

Just always remembering to bring that sense of joy and respect and curiosity to all my projects. These stories are super important and our job is important, and art is a very important and essential part of a functioning society. But, to remember not to take ourselves too seriously, but take our work very seriously, and just always approach everything with that sense of joy and gratitude. That’s what really crystallized for me.

There’s a lot of dysfunction in the TV world and in writers rooms specifically. There’s this tacit sort of acceptance. Sometimes there’s a sense of if you get this great product, it’s worth low-key abusive and toxic workplaces. But it’s not true, and this show is living, breathing proof of it. I really give credit to Issa and Prentice for doing it. I think it’s been proven — and it’s not just by our room, but rooms all over right now. All of these old methods of working really need to die because they’re not necessary, and they never were.

How has “Insecure” changed your life?

It was really wonderful just working on “Insecure” because the characters are around my age, the characters are kind of living a life that I have lived — being broke in a big city and trying to start your career. I recognize the women as people that had been in my life, that were currently in my life. It was just a very freeing, warm, loving environment that Issa and Prentice created where we felt very comfortable sharing stories from our lives and mining things from our lives. Before this I had worked on sketch comedies, so this really allowed me to grow as a grounded writer who could, in a comedy show, explore both comedy and drama.

“Insecure” changed my life in the sense that it made me really drill down into character and not be so obsessed with a joke every third line. Finding the comedy in more of the relatability rather than sort of this invented heightened realism that you find in other types of comedy. I think it just made me a better writer overall.

What does “Insecure” mean to you?

I started out as an actress and I had people in college telling me, “Oh, you’re too dark to really make a run at being an actor.” I had a friend say that to me. So, it was cathartic and beautiful to watch this gorgeous dark-skinned woman, who not only was starring in this, who was a romantic lead, but who was also the creator of it. I always say that both she and Tina Fey were sort of the blueprint for me in wanting to be both a performer and writer.

Having started working in this business, seeing how rare and beautiful it was to see us on-screen depicted so realistically, and allowing these characters to be messy and human. This was something that I had never really seen. I was a fan of “A Different World,” “Girlfriends,” and all those Black sitcoms from the ’90s, but this was different in the sense that it was getting deeper into these characters and allowing them to be messy and make mistakes. It meant a lot to me to know that it was possible, that the type of television that I wanted to see was out there.

What lessons have you learned from working on this series?

What I’ve learned from Issa and Prentice is just the real deep exploration of character. I don’t think that I did that as much as a comedy writer before. I think I was chasing a joke mainly, and I think that this made me learn to look deeper into the characters. What I learned was courage through “Insecure.” It’s okay to sometimes let your characters make unpopular choices because that’s real. That’s reality and that’s life. That’s what makes something more compelling in a way because you can see yourself in the mistakes that you’ve made in them. It makes for deeper and more compelling work.

How has “Insecure” taught you to dream differently about your path in Hollywood?

I think that it has opened doors for people like me that are looking to make complex work about Black women. So, I’m thankful that through this show people have seen that these things can be successful. Because that was what people were saying for a long time, “Oh, the reason why we don’t have a lot more diverse things is because people won’t watch and it doesn’t sell overseas.” Well, I think that “Insecure” has proved that is not the case, so it makes it easier for those of us that want to make similar kinds of work. We have something now to point to like, “Look, this is something that happened and it was successful. It takes over the timeline every Sunday night.”

I have always been very optimistic as far as what is possible as far as Hollywood is concerned. I’m just excited that we have this beautiful piece of work which will last forever, and I think will go down in television history as one of the most significant comedy shows that has ever been created.

Tell me a memorable moment from being on set.

The moment that always comes back to me was that scene on the street outside of Andrew’s apartment. Kerry Washington was directing Issa and Yvonne in those deeply emotional scenes. It was really cold that night, so we were kind of huddled around the monitor. But the performances that Issa and Yvonne achieved with the direction of Kerry was just so beautiful to watch. I found myself crying. I was just so proud of them in that moment because I knew that that moment was going to be so impactful for viewers. I was just really just wrapped up in the emotion of that and it made me think of my own friend breakup. Me and my friend still don’t speak and I was like, “This is where my journey with my friend ended. We never got back together after that.” It was just a really emotional moment and those girls were so incredible in that scene.

Tell us about a memorable moment from working on the show.

I joined the writers room for Season 4, when we were in person, so that was really special to have us all together. We would do lunches and dinners together, and I liked those social moments so much because the work was fun. We’d talk about the characters on the show with everyone in that room and we’d disagree on their trajectory. Those are all really fun moments to be a part of. Once we got to working on Season 5, it was all on Zoom; it’s a little more difficult but everyone was thankful to be working and to be working on this show specifically. It was all really good energy.

How did those conversations help shape what we see in Season 5?

After Episode 1, we jump forward in time a year. That did a lot of things for us in the room and for the characters in the show. It allowed Issa and Molly to reset their friendship and get back on the same page. It also allowed us to see them evolve in their work dynamics, specifically with Issa and The Blocc becoming more of a thing. It also allowed us to have the baby actually be in the world as opposed to telling the story of Condola’s pregnancy in that year’s worth of time. At the end of last season, we saw a lot of talk online about Condola not actually being pregnant. But yes, she is actually pregnant, and Lawrence is going to have to deal with it. We wanted to tell a story that feels honest and true to the development of the characters up until this point. So Episode 3 felt like a good opportunity to make that a Lawrence-centric story. We felt like seeing him in San Francisco would be really interesting and this idea of him growing into fatherhood and growing into the new person that he wants to be.

How has “Insecure” taught you to dream differently about your path in Hollywood?

I’ve been really fortunate to work on shows that I’ve been a genuine fan of before going into it. “Insecure” is no different. Before joining the writers’ room, I was one of those fans who would meet up with friends to watch “Insecure.” So from a fandom standpoint, this was an absolute dream. At a deeper level, I was inspired by seeing the way that Issa moves and collaborates and is so prolific with the projects that she works on and seeing how hard Prentice works. To see the two of them as Black people in leadership positions, I was soaking it up the whole time. I’ve had goals and dreams for a long time but I think working on “Insecure” and seeing people in positions that I aspire to and doing it in a way that is so dope made me respect and admire them even more. To me, it shows that I can achieve that level.

How has “Insecure” changed your life?

I like to think of Issa and Issa Rae Presents as a seed. Issa planted that initial seed, and allowed it to grow. And then that sprouted so many other branches, and there’s so much fruit that we are all able to benefit from. And now we’re all able to go off and create our own trees and create our own roots and build our own legacy because of her, and because of the platform that she put in place. So it’s been great to not only be mentored by her, see how she works and see how she does things, but also having the opportunity to embody that effort for ourselves.

When I think about everyone, all the other writers from the show, and the platforms they’ve been able to create, it just feels right that everyone has a similar vision of how they want to move the culture forward, outside and inside entertainment.

Is there one “Insecure” character you wish you could build a bigger world around?

I have two characters. The first character is Ahmal. I feel like Ahmal, being a gay Black man, there are stories that haven’t been explored. I would love to build out his world, a Black gay male world of LA. What does that look like? And also, I mean, Kelli Prenny. It would be so much fun to write, and to get into the deeper layers of her character. Not that “Insecure” hasn’t done that, but I want to know what Kelli plays up when she goes home.

What’s a lesson you’ve learned from working on the series?

My biggest takeaway is how to operate my own room. How would I want that to go? And it’s very much like how “Insecure” is run. And that is because of Prentice Penny. It’s great to see a Black man as showrunner, and to know that that could be me and that will be me.

How did “Insecure” teach you how to dream differently about what your path in Hollywood may look like?

It’s shown me that I am capable of doing multiple things at the same time, and doing them at a level of efficiency that each project deserves. Issa and Prentice are very good at compartmentalizing their work, and achieving all of it. If I’ve learned anything, it’s to apply that type of thinking to my work ethic.

We’re in the writers room, and it was the week that Issa was doing “SNL.” Based on how involved the host wants to be, they’re helping to write the sketches. They’re in rehearsals for sketches. It’s a demanding week. So there was a point where we were in the writers room, and Issa wasn’t with us that day or that week, because she was at “SNL.” And we were like, “She’s not going to look at these notes tonight. She’ll probably look at them tomorrow.” Tell me why she’s emailing them in the middle of the night. And that’s her work ethic. You can only be inspired by that.

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