Issa Rae laughs mightily—it’s a ringing laugh that may be familiar to viewers of her hit HBO show, Insecure. It’s the laugh we get when she’s nailing her impeccable comedic timing while in character, except that this laugh is unscripted. As her current fit of giggles starts to settle into a melodic minor scale, Rae is being her most authentic self: part brainy, part silly and playful, and wholeheartedly confident. That absolute confidence is a gorgeous thing to behold, especially when the playful part of it is winning out, as Rae launches into a story about her current quandary: a delightful take on her growing fame and the physical transformation happening right before our eyes.
Someone, she says, had tweeted something that made her see herself in a way that she hadn’t quite allowed herself to before. While on location in New Orleans, where her mother hails from and she’s shooting the romantic comedy The Lovebirds, she says, “In my mind I’m just like, I’ve got to lose weight. I’ve been wanting to lose weight all these years, and I’ve been basically pussyfooting. I really need to step it up. The TV show gave me an excuse. You start to become more cognizant of your appearance. But I realized the response to that changed recently. Because I was looking through tweets maybe a couple of months ago, and these girls were shading me but backhand-complimenting me about how wack I was. And one of the tweets was, ‘And that stupid bitch! If I looked like her, then I would never feel insecure.’ And I was like, What?!”
She laughs again, harder this time, at the very idea. It’s the kind of laugh that forces you to join in, even though you totally get the Twitter Thug consensus: Issa Rae is too fine to be insecure. Anymore. Folks think that a woman who rocks a smart, enviable collection of say-it-with-your-chest T-shirts and looks as good as Rae—bright smile; popping melanin; meticulous hair, whether she’s sporting a curly ponytail in a Drake music video or cornrows mixed with auburn-tinted 4C-pattern ringlets—shouldn’t ever have moments of self-doubt.
Oh? Fancy that.
As corny as it sounds, I want you to just like my mind.ISSA
Jo-Issa Rae Diop came on the scene 34 years ago, the daughter of a pediatrician from Senegal and a teacher from Louisiana. Her parents met in France while they were students. Rae is one of five kids in a family that moved from Los Angeles to Dakar, Senegal, to a tony Maryland suburb right outside of Washington, D.C., and then back to the upscale Los Angeles neighborhood of View Park-Windsor Hills.
In all the places where Rae lived, her childhood—like so many little brown girl coming-of-age stories—was defined by a sense of otherness, of being too skinny, too thick, too light, too dark, too Black, too wannabe. In Maryland she was a fly in the churn of buttermilk; in Los Angeles she was an oreo. “My parents helped me and they hurt me,” she reflects. “My mom was extremely pro-Black, and I believed her. My dad is Senegalese, and I grew up around my dark-skinned cousins and just thought that they were the most beautiful women in the world. I was surrounded by beautiful dark people. And then middle school hit, and I was like, Oh, they think I’m ugly. They think I’m big. They think I’m unattractive. I went back to my mom like, ‘What the f—k?! Y’all lied to me my whole life. What is this?!’ I started realizing, Mom, you’re light-skinned. So I don’t know what you were talking about. It’s not like you can relate to being dark. And your hair is not the same texture as mine. So what do you know about telling me I’m beautiful? Why would you lie to me? That definitely had an impact on how I saw myself.”
Rae wasn’t the first girl picked for romantic entanglements. But she also wasn’t the type to sit around on the bench feeling sorry for herself. Instead she focused on “being smart, being accomplished and being respected. As corny as it sounds, I want you to just like my mind,” she says. “I think a part of it just came from figuring out that the guys I like, I’m not their type. Learning that early on made me realize there’s no point in valuing the physical, because it wasn’t going to get me anywhere. So what can I control, and what can I bring to the table? How can I be valued in this way?”
And who were these fools not valuing Rae 20 years ago? “They were just n——s,” she says and then breaks into a fit of laughter. “I’m glad a lot of it didn’t work out. I was really into cool guys. I was into very high school muscular, college muscular dudes. I was just like, If I’m attracted to you, then what’s the problem?”
But did the—let’s call it lack of response—feel like rejection? “I guess, after a certain point,” she says slowly. “After I learned they weren’t checking for me like that, I just kind of stopped caring in that way. That’s not my primary focus. I’ve always been kind of flippant about relationships and men in general.”
Turns out that was a good thing. It was the indirect inspiration for the work we know her for best, the work that launched her and led to so many other amazing opportunities—like being one of the new faces of CoverGirl and costarring in, and quite frankly shining in, a flick like Little (in theaters April 12), in which she takes a hilarious turn as the guardian of a shrunken CEO. “Issa comes with this fierce intelligence about the whole film,” says Tina Gordon, the movie’s director. “She’s effective, productive; she sees the big picture. And I think she brings all of that experience into the room with her as an actor. I can just always see Issa’s mind working. She’s just a thoughtful actress who’s experienced every role imaginable—writer, producer, probably caterer, everything.”
This trajectory all began with her breakout web series, The Mis-Adventures of Awkward Black Girl, which became a must-watch on the Internet after it premiered in 2011. She worked with Girls Trip scribe Tracy Oliver (who also penned Little) on the project. In 2012 Rae earned a Shorty Award for best web series, a coup for a show representing a Black millennial nerdy girl trying to figure it all out.
“When you don’t have much to do or you don’t have plans on Friday night, you’re making up a character who does,” she says. “That was an outlet for me. I fantasized all the time about having a different life. And that manifested in creating characters and worlds and scenarios. I’ve definitely let my imagination run free.”
In 2019 Issa Rae is doing the work for throwback Issa Rae. The Issa Rae in middle school and high school who wasn’t getting the love she expected as she left the comforts of her home and ventured out into the world. She’s getting it now and then some. But that heightened visibility hasn’t altered who she is.
“At the core of it, Issa is still who she always was,” says Prentice Penny, Insecure’s showrunner. “And in terms of the imagery of a chocolate sister with natural hair being unapologetic about her look, unapologetic about the clothes she wears, unapologetic about her sexuality, I think that is still not the norm.” It’s why Insecure is all about making Black girls and women feel seen, the way Rae felt seen when she saw Kellie Shanygne Williams bring Laura Winslow to life on Family Matters as the ideal girl who was pretty and smart and popular—and brown.
“I’ve definitely thought about middle school me looking through magazines and being perfectly content with the fact that my face wasn’t going to be used to sell makeup; that wasn’t my future,” Rae says now. “I just didn’t imagine that. So the fact that it happened is like, you just never f—ing know. And you should never discount anything. I think so many of us tend to be comfortable with what we’re not and complacent with what we’re not. You really don’t have to be. I didn’t solve world peace or anything—it’s not like that. But something that felt so small and intangible ended up being tangible. And that’s just the coolest thing in the world.”
Kelley L. Carter (@KelleyLCarter), a metro Detroit native, is a senior entertainment reporter for ESPN’s The Undefeated. She’s based in Los Angeles.
Photographer: Itaysha Jordan –@itayshaphoto
Stylist: Jason Rembert – @jasonrembert
Hair: Felicia Leatherwood – @lovingyourhair
Makeup: Joanna Simkin – @joannasimkin
Manicure: Vontrell Jiles – @sparklev789 and Katalina Mitchelle – @katalinadoesnails
Special thanks to Preservation Hall in New Orleans.