Issa Rae, one of the first black women to create and star in a premium cable series and potentially the hardest-working person in Hollywood, is putting in overtime with the aim of having it all. She is Emmy-nominated. She is Golden Globe-nominated. She is a writer, an actor and an executive producer, often all at once. Her hit HBO show, Insecure, which just aired its fourth season, has transformed her into the patron saint of black millennial creatives. She is the black Madonna, adorning endless mood-boards.
Fans, black fans specifically, don’t simply watch Insecure, we live-tweet it, we argue about it, we create petitions for it to be extended to one hour, much to the chagrin of its creator. “We sold a half-hour comedy,” Rae tells me when I press her on fan demands for longer episodes, “and I literally have no desire to make an hour show!” A bad Zoom connection means I can’t see her, but I can hear the smile. She is warm, witty, and a total potty-mouth. “Even hearing people say: ‘This is how you can make it an hour, you can do this, you can do that…’ OK, well we don’t want to!”
To the uninitiated, the 35-year-old’s rise to the top of Hollywood appears immediate, as though she exploded on to TV screens and into critical acclaim in just a few years. But to fans, her triumphs are long overdue. Next year marks a decade since her break-out comedy web series, The Misadventures of Awkward Black Girl, debuted. (It ran until 2013, on Rae’s YouTube channel.) Awkward Black Girl was the primordial goop from which Insecure spawned. And for both series Rae mined her misfit youth for stories.
She grew up middle class, her father a Senegalese paediatric doctor and her mother a teacher. In childhood, her family moved a great deal, first to the primarily white suburb of Potomac, Maryland, then to Senegal, until they finally settled in LA. Issa was in the sixth grade then – an 11 year old. She was one of the only black girls in her elementary school in Potomac and then the only American girl in her elementary school in Senegal. She struggled to belong in each setting. When she started at a school in LA, attended by predominantly black and Latino students, she found herself the subject of the ballad of many black middle-class teens – “too black for white kids, too white for black kids”. When Tupac died in 1996, she attempted to find common ground with her mourning classmates and mispronounced his name, becoming a social pariah in the process.
Before Awkward Black Girl, there was Fly Guys Present the “F” Word, a 2009 YouTube show that followed a goofy group of aspiring rappers, her brother among them. And before that was her first web series, Dorm Diaries, a satirical look at black life at Stanford University in 2007, where she majored in African and African-American studies. A fan of the wry humour of Seinfeld and Curb Your Enthusiasm, she was also heavily influenced by black sitcoms like Living Single and Moesha – and it was after attending the set of that latter show in the 1990s she realised she wanted to break into TV. Rae set about creating shows online that spoke directly to black audiences and simultaneously bypassed industry gatekeepers. Awkward Black Girl ran for two seasons and was financed partially by Pharrell Williams, who put season two on his YouTube channel. Rae was at the forefront of the first wave of digital black talent to successfully transition into the mainstream, something she doesn’t consider as crucial today.
“People are comfortable with their talents staying online,” she explains. “Back in my day, there was like more of a, ‘Ah man, this should be on TV, this should be a movie’ or whatever, but now it feels like being online is just as viable and just as lucrative.”
Not all web series translate to television, but when Rae landed the HBO gig, her profile soared. It is testament to Insecure’s quality that a 30-minute sitcom influences Twitter discourse globally so much of the time. Following the highs and lows of LA-based best friends Issa Dee and Molly Carter, Insecure fosters frank conversation within the black community on a myriad of invisible issues: mental health, bisexuality, open relationships. Yet it is, by Rae’s own admission in a 2016 interview, “a show about regular black people being basic”. Situations aren’t life or death and fans obsess over the messy minutiae of characters’ daily lives. It is radical in its regularness.
At the height of season two, in 2017, social media-monitoring tool Brand24 estimated that the show’s accompanying hashtag #insecurehbo had a reach of more than 11 million.
“It is a compliment and a burden that people take so much ownership over the show,” Rae says, “because there aren’t a lot of shows about us, so people feel like you have to tell all the stories that can be told, and if you don’t you’re failing us.”
After transitioning from our computer screens to our TVs, she is now dominating the silver screen, too. Last year, she starred in body-swap comedy Little and this year, in two romance films: The Photograph, alongside Lakeith Stanfield, and The Lovebirds, with Kumail Nanjiani. She executive-produced both. She remains awkward at heart however, saying she “dreads shoots”, however frequent they’ve become (“I have a shoot right after this call and I don’t enjoy them, so I always have champagne handy!”) This increased visibility, as well as the added complication of sharing a name and face with her character on Insecure, has made privacy a priority.
“People have a lot of shit to say and I just don’t want it to be about me, unless it’s talking about my work,” she says. “People fill in the blanks about my own life because of the characters’ choices, but I’m fine with that. As long as it’s not my real shit and it’s wrong then talk away!”
This September, she’ll be playing a less relatable, easier to distinguish character – a billionaire’s daughter, in Jay Roach’s socially distanced comedy for HBO comedy, Coastal Elites. “Coastal elites”, the term, is defined by Urban Dictionary as “intellectual, educated, economically advantaged people in states like Washington, Oregon, California”. It follows five characters as they navigate the pandemic and an increasingly polarised political climate. “I actually had never heard the term ‘coastal elite’ until this movie so I’m just like, “What does this mean? Oh OK, it’s me.” Rae and her character, Callie, both live in LA, and they’re both “outraged by the current administration”.
“You see so much of the concentrated fuckery of this current president in one place,” she says. “Hopefully you’ll watch the movie and say, ‘This is not normal. I should be upset, I should be outraged.’ Satire or not, we’re living in this and to accept this is to be part of our own destruction.”
Coastal Elites is just her most recent project in an ever-expanding list.“Do I get burned out? Hell yeah!” she exclaims. “That was why I took a break last year, because I didn’t really think about how to do everything and do everything well. But it’s not just me – I get a lot of credit, but I work with really great people.”
We spend a great deal of the interview talking about others: ensuring that everyone else is paid their dues, past and present, is a big priority for her. In 2014, she founded ColorCreative, an organisation which acts as a springboard for underrepresented writers in TV and film. She was inspired to start the initiative after reading the script of a young woman who is now a writer on Insecure. “Reading that [script] changed my life for the better and it changed hers for the better,” she adds.
Last year, she also co-founded a music label, under Atlantic Records, an “audio everywhere company” designed to cultivate exciting new talent and empower independent artists. Whatever the industry, shining a light on black talent is imperative.
“Because I’m a fan and because I love to see us win”, she explains. “Because I recognise how much it has shaped me throughout the years. Why would you not? Why would I not?”
These community wins appear to slowly be becoming more frequent. In July, 34.3% of the acting nominees for the Emmys were black, and Insecure was nominated for eight, including Rae’s nomination for lead actress. If she wins, she’ll make history as only the second black woman to win in the category since 1981. A shadow is cast on the achievement by the fact that so many who came before her have been historically overlooked, however. It isn’t bittersweet for her, she says. “I don’t even see the sweet in it, really.
I’m not gonna be proud of being the second person, by any means,” she continues. “I was thinking about how so much of the canon of my childhood were black shows and how few of them, even in the best comedy category, have been recognised. I can’t believe Fresh Prince hasn’t won anything or even Family Matters – those shows have shaped, regardless of race, so many US youths and even the world youth. It’s astonishing that our talent hasn’t been recognised in that way, but not surprising.”
While diversity within Hollywood increases, it remains a complicated conversation. Increasingly, black, non-American actors such as Cynthia Erivo and Daniel Kaluuya have been condemned for depicting African Americans in films (there was a backlash at British Kaluuya being cast as US revolutionary Fred Hampton in Judas and the Black Messiah). It’s a criticism that has been levelled at Rae herself, as well as her co-star Yvonne Orji, despite being raised in the US, since Orji’s parents are Nigerian and Rae is half-Senagalese. What does she make of the growing debate?
“It’s just another way to divide us, unfortunately,” she sighs. “Seeing Daniel Kaluuya in that Fred Hampton trailer, I was like, go the fuck ahead! You transformed, you’re an actor! Sometimes I’m pleasantly surprised when I’m watching white shit and I’m like, ‘Oh! The bitch is Australian? That’s so dope! I would have never known.’”
It’s these intracommunity battles that affect her most. In 2017 an off-the-cuff remark she made at the Emmys during a red carpet interview went viral after she said she was “rooting for everybody black” at the ceremony. I suggest that it cannot feel particularly good when it seems that everybody black isn’t always rooting for you.
“There’s probably nothing that hurts me more than that,” she says. “You don’t want to be a disappointment. I know what it’s like to see Kanye and just be like, ‘Bro what happened?’ Or you know, Stacey Dash [a Trump supporter] like, ‘Girl, I loved you in Clueless – where did we go wrong?’ I want to make us proud and I think that goes to the Denzel of it – there’s just something special about him. He feels like ours, our movie star and he has done right by us.”
Perhaps, I suggest, Denzel Washington’s spotless reign comes from the fact his status was cemented in a time before Twitter. “True,” she muses. “I mean, him being in that Julia Roberts movie [The Pelican Brief]?” she laughs. “He would be dragged!”
As we gush about Denzel, she speaks about how much she admires his legacy, something that she feels is crucial in a world where 15 minutes of fame is now a near birthright. Sure, her impact is undeniable. But she maintains she hasn’t even scratched the surface of what she hopes her legacy will achieve.
“As far as legacy is concerned, I have so much to do,” she says. “And I’m fine with that, but it definitely keeps me up at night. My feet aren’t firmly planted just yet. I’m still walking, I’m still paying my dues, in a way that I’m not mad at. I want to earn being here.”
Insecure series 1-4 are available to watch now on digital
Styling by Jason Rembert; hair by Felicia Leatherwood using Lawrence Ray Concepts; makeup by Joanna Simkin for The Wall Group using Fenty Beauty
