Issa Rae: Not-So-Insecure
Entertainment

Issa Rae: Not-So-Insecure

Interview by Tracee Ellis Ross / Photography by Zamar Velez / Styling by Jason Rembert / Intro by Bianca Gracie

Black women have historically appeared in television and film as a myriad of demeaning stereotypes: The maid, the "ghetto" best friend, the nanny, the poor mother with a number of baby daddies, the bitch. That is, if they've appeared at all. Actresses, directors and showrunners continue to fight against these tropes that ignore the many facets of Black women's identities. And for the millennial generation, Issa Rae has helped lead the charge.

The Los Angeles native got her start on YouTube with her Shorty Award-winning Awkward Black Girl web series, produced by friend and fellow Stanford graduate Tracy Oliver. Premiering in 2011, Awkward Black Girl followed J (played by Rae) as she dealt with uncomfortable situations, from annoying co-workers to weird dates. The writer/producer/actor's YouTube channel continued to grow, as she showcased her witty and relatable writing skills with other series like Ratchet Piece Theater, The "F" Word, Roomieloverfriends and The Choir.

Top: Phlemuns, Pant: Tier, Shoes: NYAS, Earrings: J Alxndra, Necklaces and rings: Johnny Nelson

Rae's trajectory went into overdrive once HBO picked up the comedy-drama pilot she was working on with fellow Los Angeles native and The Bernie Mac Show creator Larry Wilmore (his credits also include The Daily Show, The Nightly Show with Larry Wilmore and Black-ish). Thus, Insecure was born. A riff off Awkward Black Girl, the series broke stereotypes by authentically capturing the everyday lives of millennial Black people as they traverse through jobs, relationships and friendship. Since its premiere in 2016, Insecure has raked up Golden Globe and Primetime Emmy nominations.

2021 marks two major career milestones for Rae: the 10th anniversary of Awkward Black Girl, and the fifth and final season of Insecure. Upon her entrance into the entertainment industry, she has created safe spaces for burgeoning talent to thrive while simultaneously building an empire (which also includes her Raedio record label and the newly announced Rap Shit HBO Max comedy series co-executive-produced by the City Girls). So who better to call to reflect on Rae's career than Tracee Ellis Ross? From her lead roles on Girlfriends to Black-ish, Ross (like Rae) has shifted the narrative of how Black women are portrayed onscreen.

The two women have more in common than just being actresses and content creators; as friends, they share a sisterhood that's so unique to Black women. Naturally, that bond was beautifully unveiled in conversation.

Clothing: TLZ L'Femme, Shoes: By Dose, Jewelry: Jlani Jewels

Clothing: TLZ L'Femme, Shoes: By Dose, Jewelry: Jlani Jewels

Tracee: I'm so happy to talk to you, we haven't seen each other in a couple weeks. My first question to you is, what did you want to be when you grow up?

Issa: I'm really thrilled that you're doing this with me, I specifically requested you because I remember you being one of our initial supporters of Awkward Black Girl at that ABC party.

Tracee: I have that picture somewhere that we took. I was so excited!

Issa: Well it mattered, so thank you. To your question, I wanted to be a dinosaur and a writer when I grew up. I remember that distinctly.

Tracee: I don't think the dinosaur dream has worked out so great. I encourage you to really live out that part when you can.

Issa: You know what, I will. I appreciate that advice.

"You're meant to be competitive. You're meant to act like, 'I'm creating this new thing.' But we're constantly standing on each other's shoulders [...] the difference between now and then is that we're helping lift each other up at the same time."

Tracee: So you wanted to be a writer, and that turned out great. Awkward Black Girl, can you take us back to that moment of the first episode?

Issa: I was extremely terrified. I had been creating content online that was mine technically, but it featured other people. I had never featured myself. I'd seen the comments on people I'd featured and they were mostly positive, but when I saw the negative ones I was like, "Oof, glad that ain't me." And so I put myself out there and it just felt different. It was a story that felt so specific to me, it was specifically my sense of humor and there was no one else to hide behind. This is my project and I would be blamed if it turned out shitty. I was scared as hell, and if my best friend wasn't there to watch the first cut and tell me, "Oh my God this is hilarious, take out this, this drags too long," then I would have been poorer for that. So I thank her.

Top: TLZ L'Femme, Pants: Lionne, Shoes: NYAS, Jewelry: Jlani Jewels

Top: TLZ L'Femme, Pants: Lionne, Shoes: NYAS, Jewelry: Jlani Jewels

Tracee: On this incredible journey, what has it been like to have friends that you've had for so long walk through it with you?

Issa: It's so funny, when you mention the friends, you know the image that came to my mind? My friends party with you. Getting you to dance, getting you to twerk. It's kind of violent, in the best way [Laughs]. That foundation is incredibly important to me. If it doesn't work out, I can always turn to them. And there's no judgment. It's incredibly important for me too to have a space outside of the industry, because as you know people will define your success by what you were able to accomplish. That seems insane to me. I never want to feel like this industry defines who I am, and also what I create, you know?

Tracee: It's really fun, Issa, to see the evolution of how one story starts to give birth to the next generation. I'm 10 or 12 years older than you, and Girlfriends preceded Awkward Black Girl. There's so few Black stories, because we're still under that guise that we're supposed to be competing against each other, which I think is bullshit. That sisterhood is part of what keeps us all going.

Issa: We're swimming in the same waters, and Girlfriends undoubtedly birthed the opportunities that I and other creatives have had. That knowledge came in the pilot episode of Insecure, when we sing Girlfriends at the end, which was written before I knew that Prentice Penny [from Girlfriends] was going to be my showrunner. It's so important to acknowledge, because to your point, you're meant to be competitive. You're meant to act like, "I'm creating this new thing." But we're constantly standing on each other's shoulders, and I think the difference between now and then is that we're helping lift each other up at the same time.

Tracee: You learn some really interesting things making television, and I'm curious what some of those pearls are?

Issa: Definitely to stop being afraid to speak up, to say no, don't try to please everyone. Make the show that you want to make. That was something that I learned thankfully early on, through great mentors shepherding me into this industry. That has been incredibly helpful to my own confidence. I think I need to step back and act like I'm going to be here for a while, because it will impact the decisions that I make in a better way. I have to bet on myself. It's scary because there are so many pressures out there and I'm trying to learn not to put pressure on myself. Because that can dictate what you can and cannot do.

Clothing: Sammy B, Shoes: Keeyahri, Earrings: Jlani Jewels, Rings: Johnny Nelson

Clothing: Sammy B, Shoes: Keeyahri, Earrings: Jlani Jewels, Rings: Johnny Nelson

Tracee: How do you keep navigating your own dreams in a world where people have limited ideas about you, no matter how big you get? I was looking back at your book, which talked about not feeling Black enough. I remember we actually had a lot of fights about this on Girlfriends, trying to define Blackness in certain ways, and it was something I kept pushing up against. It's really reductive. The Blackest thing I've ever done is be myself. How do we expand people's idea of who we are?

Issa: I think we do that by reclaiming these narratives, by empowering these other voices. I still see the industry dictating in advance what Black stories are worth being told. And that is a little bit frightening to me. Because it feels like we're evolving over time, but there's still a greenlighting power that we haven't yet grasped yet.

Tracee: There's still a sense of gatekeeping: deciding which stories are sellable. We keep building other tables but there's still a center. As Black women, historically we have not had a stake in what we make. But Black women are the leaders of our lives. You look at Cicely Tyson. She had this platform. And she knew that she was going to use it, to do what she could, and that was to give voice to the dignity and humanity of our Blackness. Black women, Black people. She was a giant in the space she created.

Issa: It's also beautiful to see that the people she ultimately inspired and opened the door were the first ones to remember her, to uplift her, to hire her again. The longevity of her career is the result of the doors that she opened.

"If you're going to celebrate Black history, celebrate Black people all year long. And understand that it's also your history."

Tracee: That's a really nice thing to remember. Do you think now, a web series like Awkward Black Girl is still a viable path for young creatives?

Issa: One of the things that is terrifying about Awkward Black Girl is if it had come out a year sooner or a year later, I think I would have missed the mark. I think a web series is still viable, there's still opportunities to get hired via doing one, but I think that was a very specific moment because it was a response to what television wasn't doing. Maybe at this time I'd be trying to work out what I was doing on TikTok. I'd find a way, but I don't know if it would be a web series.

Top: Phlemuns, Pant: Tier, Shoes: NYAS, Earrings: J Alxndra, Necklaces and rings: Johnny Nelson

Top: Apartment 202, Pants: Lionne, Earrings: Jlani Jewels

Tracee: We're now in Black History Month. What does that mean to you?

Issa: I saw this billboard downtown today that was like, "Black culture is culture, so keep on making culture." I was like what the fuck is that? This billboard in the middle of downtown talking about Black culture? Then I realized, Black History Month! Okay, that's why we're getting props. And that side of it is frustrating to me. I'm of the mindset that Black history is American history. So I'm a little bit over it. When I think about Black History Month I think about the forced, "Okay, now it's your time, let's hear about your history, good for you, Black people." If you're going to celebrate Black history, celebrate Black people all year long. And understand that it's also your history. But I don't feel particularly moved by Black History Month.

Tracee: You recently opened a coffee shop and a record label. You lean into all these different aspects of who you are — what's the common through-line for you? Or are they satisfying completely different parts of Issa?

Issa: They're satisfying completely different parts. The music side in particular, I simply do not have that talent, and I have so much respect for musicians, people who can sing, people who are inclined in that way [Laughs]. So when the record label opportunity came, it was like "Yes I want to do this." I do this with writers, so why not do the same thing with artists?

Tracee: I think that'll keep you having a juicy life, rather than being in one lane. We all have all these different sides, and somehow we pick a career and are supposed to stay in that. Moving into other areas, it's been really fun for me doing that, and I think it's fantastic that you do. It gives other people the example that it's okay to be many things. You don't have to just do one thing.

Issa: There's an impact that we all want to have, to have a specific voice to make change, and there's only so long that you can say you're doing it through your art and your work. I want to be active elsewhere.

Tracee: Now I have some lightning round questions. Name your top three artists or songs right now.

Issa: I'll say right now, Giveon. Is T-Murda [Ross' rapper alter-ego] still rapping, or did she give up?

Tracee: Yes she did! [Laughs] 2020 was not kind, T-Murda went down!

Issa: I'll also say Yung Baby Tate's "I Am," and Jazmine Sullivan all day every day.

Clothing: TLZ L'Femme, Shoes: By Dose, Jewelry: Jlani Jewels

Clothing: TLZ L'Femme, Shoes: By Dose, Jewelry: Jlani Jewels

Tracee: All day. Favorite thing to touch or smell?

Issa: What the fuck Tracee? [Laughs] I love when candle wax is hot and gets hard, that's my favorite.

Tracee: What was your first job?

Issa: I was babysitting cats. And that's how I found out I was allergic to cats.

Tracee: Sunrise or sunset?

Issa: Sunrise.

Tracee: Liquid soap or bar soap?

Issa: Bar soap all day.

"I think I need to step back and act like I'm going to be here for a while, because it will impact the decisions that I make in a better way. I have to bet on myself."

Tracee: Really?

Issa: No Tracee, don't. Liquid soap, really? [Laughs]

Tracee: I'm so liquid soap!

Issa: With bar soap you really get in there!

Tracee: This is why the lightning questions are fantastic. Pool or beach, and then I'll let you go.

Issa: Pool.

Tracee: Okay, I'm pool too.

Issa: You do love a pool.

Clothing: Sammy B, Shoes: Keeyahri, Earrings: Jlani Jewels, Rings: Johnny Nelson

Clothing: Sammy B, Shoes: Keeyahri, Earrings: Jlani Jewels, Rings: Johnny Nelson

Photography: Zamar Velez
Photography assistant: Samone Zena
Styling: Jason Rembert
Styling assistant: Shameelah Hicks
Hair: Felicia Leatherwood
Hair assistant: LeRae Burress
Makeup: Joanna Simkin
Nails: Yoko Sakakura
Production: Brandon Zagha

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