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With a TV show, movie roles, a recording studio, café, and more, it seems there’s nothing Issa Rae can’t do. Here, she discusses Insecure’s new season, her love of South L.A., and embracing feminism—despite its “tinge of whiteness.”

Despite starring in her own hit HBO series, Insecure, executive-producing another, A Black Lady Sketch Show, and, oh yeah, continuing her trajectory as a full-fledged movie star that started with The Hate U Give (2018) and Little (2019) and is now ramping up in 2020 with romantic leads in The Photograph and The Lovebirds (out later this year), Issa Rae still isn’t comfortable with the idea that she’s famous. “It’s weird to think about,” says Rae of fame. But she does remember the moment she realized people knew her name, and her megawatt smile.

“A few years ago someone tweeted a picture of Gucci Mane at a basketball game smiling,” says Rae, a fan of the rapper, who, like her, is known for his large, toothy, and infectious smile. “The caption was something like, ‘Gucci Mane out here looking like Issa Rae.’ And it had like 50,000 retweets!” she says, still sounding astonished. “I was like, ‘A lot of people have to know who I am for that many people to get the joke!’ I also realized that’s why I was so attracted to him—we look alike!” 

It’s been five years since HBO ordered the pilot for Insecure, the comedy series starring Rae as Issa Dee, a professionally and romantically frustrated woman living in South Los Angeles. Co-created with television veteran Larry Wilmore (The Daily Show, The Nightly Show), Insecure was a welcome alternative for so many of us who just couldn’t see ourselves in the privileged, angsty, white millennials on Girls. As Insecure heads into its fourth season on April 12, on the heels of two lead film roles for Rae, she is also producing multiple projects for the network; recently launched a record label; and has realized her dream of opening a coffee shop. Yet somehow, even as she works her BUST photo shoot with the grace of a top model, Rae still comes across as not-too-cool and very relatable, just like J, the character she portrayed almost a decade ago in her award-winning web series, The Misadventures of Awkward Black Girl. She’s got a big laugh that she breaks into easily and generously, and she makes you feel like you’re talking with one of your girlfriends. That may be because each of the characters she’s created is like the best friend we grew up with, or the first friend we made in our new office—effervescent and smart, but above all else, real. Unlike her characters J or Issa Dee, however, Rae won’t be breaking into raps to express herself. “I have no musical talent and I don’t write song lyrics. I don’t even like reading poetry,” she says with a laugh. “I said that to someone the other day and they said I was uncultured. Fine! I agree.” 

Rae, who celebrated her 35th birthday with a blowout party in January, grew up primarily in View Park, a historically Black area in the hills of South L.A. sandwiched between Baldwin Hills and Leimert Park, and just north of Inglewood. In the upper-class View Park, residents proudly show off landmarks such as the large homes once owned by Ray Charles and Ike and Tina Turner. It was here that Rae became obsessed with Gina Prince-Bythewood’s 2000 film, Love & Basketball—a romance set in Baldwin Hills—and began writing screenplays while still in high school. Rae says the movie, about two young people whose love for each other rivals only their passion for the sport, is her favorite love story. “It just inspired me so much. It will forever be my favorite movie,” she explains. Last year, Rae purchased her first house, just five minutes away from where she grew up. While most shows set in Los Angeles focus on areas like Beverly Hills and the Westside, Insecure highlights the people and places that make South L.A. beautiful, and the show is something of a love letter to the area. 

Her love for this section of Los Angeles is why, in the midst of all of her TV and film projects, Rae made time for a decidedly un-Hollywood venture, of which she is particularly proud—her new café in downtown Inglewood. Late last year, Rae announced her part ownership of Hilltop Coffee + Kitchen’s new location which follows a flagship site in Rae’s beloved View Park. Until recently, the area was a virtual coffee desert, save for a few Starbucks. “I’ve always wanted to open a coffee shop,” says Rae, a coffee lover who early in her career worked primarily out of cafés. “It’s the perfect place to network and meet people.” Caffeine-seekers walking into Hilltop Coffee + Kitchen step onto floor art that reads “You belong here,” “You are magic,” and “Keep going.” For this coffee-loving writer who is often put off by the pretentious vibes of craft coffee shops, Rae’s cafe feels like a revelation—the coffee is great, the tea is local, and the people look like me. 

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“It’s a historical fact that we’re just constantly pushed out of our own neighborhoods, and disregarded,” says Rae, explaining why this endeavor is about much more than coffee. “I think we’re the only ones who will prioritize each other. And so if we’re not creating spaces and businesses and opportunities for each other, they just won’t happen. It’s something that I’m extremely passionate about, because I’m tired of it, and I also don’t want to be part of gentrification because I understand that my socio-economic status has changed, and I could be actively displacing people. For me, it’s about making sure that other people can own [businesses and property] in their communities, and can benefit from the development.” The cafe is also walking distance from the offices of ColorCreative, the initiative Rae co-founded to find emerging writers from underrepresented groups, and help them produce their projects.

“I think we’re the only ones who will prioritize each other. And so if we’re not creating spaces and businesses and opportunities for each other, they just won’t happen.”

 

Heading into 2020, Rae participated in the “10-year challenge” on Twitter, sharing a tweet from the beginning of last decade that summed up where she was in life at that point: “still pretty livid that i’m working this weekend. #in2010 i will take the necessary steps to work for MYSELF.” 

“I was working at a museum for a slave ship exhibit,” Rae says of that time in 2010. “I was on a literal slave ship! When I tweeted that, I just knew I couldn’t give that slave trade speech ever again. It was terrible and depressing.” The following year, Rae and her co-producer, screenwriter, and showrunner Tracy Oliver, began work on The Misadventures of Awkward Black Girl, a series of 5 to 15-minute YouTube videos following the life of nerdy “J,” played by Rae, as she navigates love, work, and friendships. Most of the crew were friends who worked for free until Rae and Oliver raised $56,000 on Kickstarter, enabling them to pay a small wage and complete shooting the 12-episode first season. Everyone was learning on the job, but the result resonated with viewers immediately. The show’s popularity grew by word of mouth, and by the second season, the show was airing on Pharrell Williams’ YouTube channel. Rae was making a name for herself. “But I still couldn’t quit having a day job, so I took a job at a nonprofit,” she says

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That work experience inspired some of Insecure’s first season, which saw Rae’s character, Issa Dee, working at the fictional charity “We Got Y’all,” a hilarious depiction of white liberalism gone wrong (the nonprofit’s logo is a white hand lifting up three Black children). But while the show devotes a lot of time to Issa’s work and her relationships with men, including the polarizing Lawrence—a “good guy” boyfriend who puts zero effort into the relationship—the love story at the heart of the series is the friendship between Issa and her best friend Molly, played by comedian Yvonne Orji. 

The Issa/Molly relationship was inspired by Rae’s relationship with her own best friend. “My female friends are everything,” she says. “They’re my support system. My rocks. We keep each other grounded and lift each other up. We definitely have a group chat going.” Leaning on and supporting other women is also connected to her identity as a feminist, though she wasn’t always at ease with the word. “I probably first became aware of the term ‘feminism’ in high school. I didn’t really identify with it because it just felt very white. I didn’t take the time to really explore it. In college, I discovered Alice Walker’s version of feminism—womanism. The word feminism still has a tinge of whiteness to it, but I understand the definition of the word now. I identify as a feminist because that’s what I believe in.”

At the end of Insecure’s third season, Issa and Molly had a falling out that left viewers wondering where the BFFs would be when the new season starts. Rae is mum on specifics but says, “This season is really about growing pains. You think the growing pains stop when you’re 16, but really, they continue into adulthood and there’s no guide book. You just have to figure that shit out all while you’re evolving as a person. Sometimes you think you need certain people in your life to grow and continue and that’s not always the case.” 

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It was through Insecure that Rae connected with Stella Meghie, writer and director of The Photograph. The film is a leap into romantic lead territory on the big screen for Rae, after her well-reviewed supporting performances in the popular YA movie adaptation The Hate U Give in 2018, and in the adult-to-child body-transformation comedy Little in 2019. In The Photograph, Rae stars opposite LaKeith Stanfield as Mae, a journalist unpacking the secrets of her recently deceased mother’s love life, while navigating her own. “Stella directed the episode of Insecure last season when Nathan and Issa go on a day date,” Rae explains. “I really liked working with her. I just felt like she was romantic at heart. I liked a lot of her notes, and I’d seen some of her work. When The Photograph came along, I just really, really loved the script. Stella has such a passion for Black romantic dramas, and I missed that type of storytelling. She was thinking of me for the role, and I was so honored to be a part of this movie.” 

As honored as she was, the part proved to be a welcome challenge for Rae, who got to work acting muscles she doesn’t often have the chance to flex. “I identify as someone who loves humor, that’s what I lean on. And so for that not to be the main go-to for this particular character was a challenge. This is new for me and this character is serious and she’s dealing with loss. So any crutch that I may have had—like leaning on being funny—[Meghie] was sure to call it out and be like, ‘Uh uh, don’t do that.’”

“You think the growing pains stop when you’re 16, but really, they continue into adulthood and there’s no guide book. You just have to figure that shit out all while you’re evolving as a person.”

 

In addition to taking on her role in The Photograph, and the upcoming romantic comedy The Lovebirds with Kumail Nanjiani, Rae formed her own record label, Raedio. Music factors heavily into Insecure, from the character Issa’s own rap aspirations to the show’s soundtrack, which consistently highlights emerging artists. “I’ve always wanted to be involved in music. And I’ve been approached in the past by different record labels to be an artist,” says Rae. “But I’m not interested in that. I’m not a rapper. I just love music and I love working with creative people.” Raedio’s flagship artist is R&B singer TeaMarrr, and Rae co-stars in the music video for her first single on the label, “Kinda Love.”

“I work with a great team of people and everyone I work with has an entrepreneurial spirit, and we’re just really excited to be able to have these opportunities in the industry,” says Rae when asked how she manages so many things at once. “We focus on the things we’re passionate about, and I like to prioritize what can get done the soonest. A lot of times my own extra projects have to take the back burner just because I don’t have the time. Insecure takes nine months out of my life, every year. But right now, I’m writing a movie and I’m on deadline. I focus on my own personal projects when I have a break from the show, and when I can schedule the time to get it done!”

“I identify primarily as a writer and producer,” continues Rae, further distancing herself from the spotlight that’s followed her over the last several years. She’s warm, laid-back, funny, and self-assured, but Rae clearly doesn’t revel in talking about herself. She might be proud, but she doesn’t seem particularly impressed with her accomplishments—and it makes sense; she’s probably been this funny and brilliant her whole life. And in an age when so many celebrities are over-exposed, Rae is fairly quiet on social media, preferring to keep her private life private. It’s not inconceivable that she might just pull a Beyoncé one of these days and begin communicating with us strictly through her art and carefully crafted dispatches. It was reported last year that Rae was engaged to her longtime boyfriend Louis Diame, and though she wears a large diamond ring on her left ring finger and hasn’t denied the news, she just doesn’t talk about it, as if to say It’s not a secret, it’s just none of your business. “I don’t like attention,” says Rae. “I like to make my moves in silence, and just mind my business!” 

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By Sabrina Ford
Photographed by Shaniqwa Jarvis
Styling by Jason Rembert // Makeup by Delina Medhin // Hair by Felicia Leatherwood
Top photo: Aliétte dress; Alexis Bittar earrings; ring: Issa's own
This article originally appeared in the Spring 2020 print edition of BUST Magazine. Subscribe today!

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