In 2013, fans of Issa Rae's YouTube series The MisAdventures of Awkward Black Girl rejoiced at the announcement that the young, fresh, comedic voice would be taking over television with a pilot she had developed with Larry Wilmore. Three years later, the result – titled Insecure – is ready to launch its first season on HBO on October 9th, translating the online series' uncomfortability, funniness and pain of being a black professional in a mostly white work place, as well as taking a larger, more contemplative look at what it means to balance love, work and creativity.
"I didn't want to do an extension of Awkward Black Girl," Rae says, calling from Los Angeles. "I knew that just by nature of having me in it that there was gonna be awkwardness, and that some of the same themes would be explored. But I wanted to make something more grounded that fit HBO's sensitivities, and felt a little bit more raw and authentic to me."
Raw is exactly what Rae delivers when telling the story of her character, also named Issa, who's navigating both a dead-end relationship with her live-in boyfriend Lawrence (Jay Ellis) and a job at a largely white non-profit that works with black students around L.A. Then an ex-boyfriend comes back into her life and reminds Issa of her passion for rapping, which prompts her to tap into her creative side. Meanwhile, her best friend Molly (Yvonne Orji) is a successful lawyer who desperately wants to get married and refuses to settle for a man who is not as or more successful than her.
"I tapped a lot into my real life relationships, my real life friendships, my real life thoughts and feelings and insecurities," Rae explains of the inspirations. "When you're doing that, it does become very specific and authentic. I don't want people to look at this show and be like, 'Ah, that's what black girls are doing.' That's unfair to the story we're trying to tell, and I definitely want people to relate to it. I want people to recognize who they see on screen, but I didn't set out to be like, 'I want to tell the black female millennial story, and I want to be the voice of that' – because that's impossible to do."
Even so, Rae's existence as a "black female millennial" constantly consuming the culture around her – and the ways in which she inserts that into the show – makes Insecure feel cozier than most series that tap into this generation's approach to dating and work-place politics. In one episode, a pillow that reads "Miley, What's Good?" with a photo of Nicki Minaj — in reference to a popular, shocking moment from the 2015 MTV Video Music Awards — sits prominently on the couch Lawrence and Issa share. Elsewhere, Rae's love for modern hip-hop figures both directly and indirectly into the dialogue and soundtrack of the series. "We have a Drake lyric in every episode as an Easter egg," she reveals. "That was a personal thing for me, but that's not something that we bang you over the head with."
With the help of the show's music consultant Solange Knowles, Insecure's actual soundtrack is filled with the songs by both independent and established artists of color, from Kendrick Lamar ("Alright") to Junglepussy ("Bling Bling"). And their work isn't just being used to spice things up or add a sense of trendy currency; the tunes figures prominently into the show and its flow, serving as a reflection of the fictional Issa's own musical talent and need for expression that's re-ignited during the first season.
"I think about artists like Drake who I really love and can pinpoint albums that reflect certain times in my life," Rae admits. "But his music has literally been a soundtrack to some of the best moments in my life. I wanted to make sure the artists were as diversely reflected as possible and that anybody could play this soundtrack and be like 'Oh my gosh, this is the soundtrack to my life, too!'"
"I want people to recognize who they see on screen, but I didn't set out to be like 'I want to tell the black female millennial story, and I want to be the voice of that' – because that's impossible to do."
Knowles came into contact with Rae through Melina Matsoukas, a producer for the series who directed several episodes of the first season who had worked primarily as a music video over the course of her career. "Melina just threw it out there," she says, "like 'You know Solange is trying to get into music supervision, and I don't know if you would guys would be open to that.' I was like 'Shut up, girl! Of course we're open for that.'" Knowles, in turn, helped introduce the team to Raphael Saadiq, who wrote original music for the show, as well. "The show has just gotten better over time and with each new team member that's been added."
Examining the larger picture of the moment in which Insecure is premiering — a moment just shortly after the Emmy Awards celebrated their most diverse year yet and the white male anti-heroes of Breaking Bad, Mad Men, etc. are becoming rarer and rarer — Rae is aware of the importance of her show's existence. "I've maintained for a long time that you need voices of color behind the scenes until you have us reclaiming our stories for things to change in Hollywood, and now you see that happening," she says. "There's a renaissance, and it's so exciting to witness. It's also happening simultaneously during a time where we do feel a little bit hopeless just in terms of the constant shootings and our place in society. This renaissance really reclaims our place as human beings and as auteurs."
While Rae is continuing to learn how to grasp being named in the same breath as heroes like Donald Glover and Ava DuVernay, who both recently had TV shows premiere, she's still dealing with her own insecurities as an artist. "I still very much feel like I'm 'that Internet girl,'" she admits, in reference to her YouTube start. "I still feel an allegiance there, but I don't know that I'll ever feel like I'm a part of Hollywood. It just feels like I'm getting the chance of a lifetime to make something that's pure and authentic to me. To have more people watch it is the coolest ever, but I don't feel much different other than that."