Issa Rae: ‘Female friendships are so rich, and I feel like we’re just scratching the surface’

The actor, writer, producer who created ‘Insecure’ talks to Amanda Whiting about her new HBO comedy ‘Rap Sh!t’, and the day she realised that childhood prohibitions about sexualised female rappers were ‘essentially slut-shaming these women’

Issa Rae is making some of the decade’s most probing TV on the subject of female friendships (Jabari Jacobs)

In a proper Miami story, fun you’ll never, ever forget comes tinged with calamity. You breathe it in, along with the humidity. Issa Rae was riding home from the strip club with friends when their Uber broke down on the freeway. It was the dead of night, and the driver kicked them to the curb anyway. Rae drunkenly stumbled across speeding lanes of traffic to the nearest off-ramp. There she found an “amazing” 24-hour diner beckoning her and her friends to come in, eat fries, and laugh about the night they nearly died in Florida.

Except a fight breaks out in the diner. “This girl throws glass and her shoe at her man,” Rae tells me, her voice conspiratorial, “who must have been cheating.” The manager shuts the place down, so Rae and her friends wind up stranded in the hot, muggy night (again), this time surrounded by everyone else who chose late-night pancakes over sleep (eventually, they’d be allowed to finish the meal). “Miami’s so temperamental,” says the 37-year-old. She could easily be talking about the weather or the vibe.

And Rae knows the city. The tremendously multi-hyphenate actor-writer-creator-producer-et plus just spent six months in Miami shooting Rap Sh!t, a rambunctious new HBO comedy about an aspiring female hip-hop duo. Rae, who created and co-executive-produced the show, is heading back this week for its splashy premiere party. But unlike on her name-making HBO series Insecure, about a quartet of LA women kissing 30, the Emmy nominee remains strictly behind the scenes. Welcome to her self-declared “mogul era”. If the transition from newcomer to power player seems fast to you, that’s because Rae’s on a mission to destroy Hollywood’s wait-your-turn-and-pay-your-dues culture: “It feels so arbitrary.”

She tells me all this over Zoom, at the tail end of a press tour that culminated in the ultimate high/low double bill: a remarkable Today interview and toothpaste on her face (TV make-up is demanding). Rap Sh!t, a show so giddily profane that it has a curse word in the title, isn’t the series America’s used to seeing spotlighted on a morning chat show.

But Rae’s earned a reputation for developing shows, from her breakthrough 2011 web series The Mis-Adventures of Awkward Black Girl to its award-winning 2016 follow-up Insecure, that bake depth and pathos into stories about the basic day-to-day lives of Black women.

On the semi-autobiographical Insecure, Rae played Issa, a rudderless charity worker navigating romance and career alongside her best friends from college. Like Rae, whose father is a doctor and whose mother is a teacher, Insecure’s Issa was a Stanford grad from a middle-class family in Los Angeles. She was also struggling to keep female friendship at the centre of her life in that tricky moment when people evaporate into marriages or, worse yet, see their personalities subsumed by their five-year plans.

Friendship is the obvious through-line from Insecure to Rap Sh!t, a show about childhood pals who make music together. For Rae, this is TV’s unexplored frontier.

“Female friendships are so rich, and I feel like we’re just kind of scratching the surface on the different dynamics,” says Rae, who, along with Lena Dunham and Michaela Coel, is making some of the decade’s most probing TV on the subject. Insecure was a five-season dig into friendships that endure through the seasons of life. But this theme takes an entirely different shape on Rap Sh!t.

“The ‘odd couple’ dynamic fascinated me,” Rae explains of her protagonists. Shawna, played by Aida Osman, is a college dropout who works hotel reception while trying to make it as a conscious rapper. Mia, played by real-life Miami rapper KaMillion, is a make-up artist and single mom with a knack for using the internet to show off her bombshell personality. When the series starts, the women haven’t spoken since high school.

Issa Rae with Yvonne Orji and Natasha Rothwell on ‘Insecure’ (Raymond Liu/HBO)

Rae might not be an aspiring rapper, but Rap Sh!t still shows off a knack for mining what’s affecting about her own life. “I just got reconnected with my middle-school best friend, and we take walks together,” says Rae, who talks about the “friendship interrupted” journey she’s on in the same dishy cadence as a “how we met” love story. “We try to see each other through new eyes, but I’m still like, ‘Girl, I remember what we was talking about in church. I remember your middle-school boy taste.’” The question she’s posing is deceptively simple: how do you get to know a woman whom you already know?

Because Rae does more than celebrate female friendships in her work. She tests them. Her sensitivity to the complicated ways in which women relate to each other is why she was compelled by the female hip-hop scene as it looks right now – the moment that she and showrunner Syreeta Singleton have labelled rap’s “Bad Bitch Renaissance”. Rae grew up listening to female rappers (“Lauryn, Missy, Kim, Foxy, Left Eye, I love them all”), but there was a tension in admiring sexualised stars like Lil’ Kim and Foxy Brown. “I was socially taught to shun them and to not aspire to be them,” Rae remembers.

But things changed for her in high school, when she and her classmates got turned on to Miami rapper Trina. “I was like, she is badass. What the f***? Why have I been so ashamed? Why has it been placed in my mind that what she’s rapping about is wrong? We’re essentially slut-shaming these women when they’re empowering themselves.” It’s the same energy she sees emanating from Cardi B and Megan Thee Stallion. “There’s an unapologetic nature to how these women are presenting themselves, how open they are,” Rae says. “Beefing” is endemic in hip-hop, but unlike in the Nineties, when women felt pitted against each other, the more intriguing story is collaboration: “Like, ‘F*** that. We could all be bad at the same time. We could all be on each other’s verses.’”

The fear lived in me that this person could’ve said anything they wanted, and people would have believed them

Rae is open and easy to talk to. She mixes her thoughts about her work with family anecdotes; she answers questions head-on. When I tell her a friend’s Miami wedding was pushed inside by rain last weekend, she’s quick to commiserate: “I would be pissed too if it was my wedding.” The actor, who got married in 2021 to Louis Diame, a businessman to whom she never confirmed she was engaged, is extremely personal without being confessional. Her answers are honest, but also controlled.

Which is notable, because Rae credits social media self-promotion for helping her find her audience. On Rap Sh!t, her characters engage in that same deliberate self-construction. They film themselves because that’s how we discover new artists, sometimes before they even reveal that they’re artists. Rae remembers watching Cardi “when she was just making social media videos, a hilarious stripper with a chipped tooth, just giving it to you”. It’s an electric kind of fandom. “When she rose, it was like, ‘Oh my God, I know her,’” says Rae. Same with clips of Megan Thee Stallion twerking at the gas station or Miami duo City Girls, who are producers on Rap Sh!t, being so online. Rae gets it because at one point it was her early fans screaming, “I just saw Awkward Black Girl on HBO!”

But she’s been famous for long enough to see the downsides to these paths to creative success, too. Recently, someone contacted Rae via social media to warn her that they were planning to reveal a rumour about her. “And I had no control over it. And I didn’t respond. And I had no idea what they were going to say,” she remembers. According to Rae, the rumour was a “big nothing”, but the incident didn’t end there. “The fear lived in me that this person could’ve said anything they wanted, and people would have believed them.” What if it had been a bigger secret or even a slanderous lie? “That is the climate and the era that our favourite artists are rising in, and part of that is really scary.”

Issa Rae with the cast and crew of ‘Rap Sh!t’ (Getty Images)

Internet fame also has a weird way of making everyone seem like an overnight success. Even before ABG, Rae was making videos, including a 2007 mockumentary about being a Black Stanford student. Last year, she inked a development deal with WarnerMedia reportedly worth $40m. On the one hand, it’s a lot of creative control pretty early in her career. On the other, she’s been gunning for this since she was a kid in Senegal, where her family briefly lived. A favourite story Rae’s mom tells involves four-year-old Issa doling out parts at the dinner table. “So I’d be like, Mommy, you’re playing Daddy,” she says. “And I would assign everybody.” The third of five siblings, Rae would even recast people if their impersonations weren’t funny: “If you weren’t giving, you had to go.”

Tellingly, even in her pre-school memories, it was never a one-woman show Rae was putting on. The actor turned exec has a reputation for mentoring, and Singleton is a perfect example. The women met at a digital workshop organised by Rae in 2015, back when Insecure was just a script. In five years, Singleton went from Insecure writer’s assistant to Rap Sh!t showrunner. “That’s not necessarily the Hollywood way,” says Rae, who found the industry’s glacial pace vexing when she was transitioning from the internet. “You really, really have to pay your dues. And someone has to determine that you paid your dues before you can be promoted. And I think, with us, we tend to be more generous. That’s not to say we’re easy, but we just recognise one another’s talent quicker.”

This may be Rae’s mogul era, but next up is a role in the new Barbie movie starring Margot Robbie. Rae won’t tell me what Barbie she plays – or even if she definitely plays a Barbie – but she gushes about being on Greta Gerwig’s set. She never saw the director frustrated; Gerwig was “always” chatting with someone and cracking jokes. “I want all my sets to be like what she was able to create,” Rae says, with a producer’s eye.

Issa Rae in ‘The Mis-Adventures of Awkward Black Girl’ (YouTube)

When rumours of an Insecure spin-off inevitably come up, Rae tells me she “regret[s] even hinting” about that, though she doesn’t completely shut down. In fact, when I suggest a show about Kelli, the fan-favourite character played by Natasha Rothwell (The White Lotus), again the producer in Rae can’t help coming to the table. “First of all, is Kelli even available? Natasha is out here killing the game. She’s in high demand. So I also have to wait until she feels like…” Rae catches herself. “First, look at you having me talking.” Then she delivers a blow to Insecure fans who watched every episode live and obsessively kept the conversation going on Twitter until the following Sunday. “If I do it, it would not be around the main four girls,” Rae says resolutely. “It would be a true spin-off.”

In the meantime, Rap Sh!t will scratch that itch for smart, well-worn female friendship. Rae says she wants watching an episode to feel like listening to your favourite female anthem, maybe a Latto song or a Megan Thee Stallion song. “There’s a specific type of energy there that I want this show to represent,” Rae tells me. “Just a good time and a journey. Like, I’m just getting in the car with my friends and riding and seeing what happens.” It’s the feeling people think they’ll find in Vegas, but really it’s in Miami.

Rae seems almost lost in her own daydream about it. That is, until her inner exec interrupts (again) to talk brass tacks: “But then also, you know, I want the makings of a good half-hour dramedy.”

‘Rap Sh!t’ is streaming its first two episodes on HBO Max in the US now, followed by one episode a week until 1 September. A UK release date has yet to be announced