Issa Rae was born in Los Angeles to an African American teacher, Delyna, and a Senegalese pediatrician, Abdoulaye Diop. She has four siblings: Lamine, Amadou, Malick, and Elize. (One of Rae’s first web series, a mockumentary called Fly Guys Present “The ‘F’ Word,” was inspired by her brother Lamine’s rap group and starred Lamine himself.) The family moved in Dakar, Senegal during Rae’s childhood. When Issa Rae was in sixth grade, her family moved to the affluent View Park-Windsor Hills neighborhood of Los Angeles, where she attended a predominantly black middle school, and she graduated from King Drew Magnet High School of Medicine and Science, where she started acting. As a college student, Issa Rae made music videos, wrote and directed plays, and created a mock reality series called “Dorm Diaries for fun”. At Stanford, Issa Rae met Tracy Oliver, who helped produce “Awkward Black Girl” and starred on the show as Nina. At the time, she used to work odd jobs and at one point was struggling to decide between business school and law school, but eventually abandoned both ideas when “Awkward Black Girl” started taking off in 2011. It’s not a bad reading for someone who built her career out of being comically uncomfortable in her own skin, literally stamping her brand with the words awkward and insecure. She attributes all this partly to her family. “We all think about the same uncomfortable situations and have very similar observations,” she says. “You could replace me with any of my siblings in Awkward Black Girl, and you would still get the same humor.”
Originally, her famous show “Insecure” seemed like a glossier version of The Misadventures of Awkward Black Girl, the gleefully misanthropic web series that helped Rae get Hollywood’s attention. “Insecure” follows Issa Dee, an aimless 29-year-old, and her best friend Molly, a polished lawyer. Issa, the character, is goofy and endearing. She’s working a dead-end job at a dubious nonprofit called We Got Y’all, the company’s logo is a white hand holding the silhouettes of three Black children and is initially stuck in a relationship with a jobless couch fixture named Lawrence (Jay Ellis). The first season was funny and sexy but grounded: Issa kicks back in her room, hangs out with her friends, and blows off steam by performing nerdy raps and aggressive duologues to her own reflection.
As the show grew, HBO became increasingly excited, upping budgets and scheduling it after Game of Thrones and Ballers, which yielded a huge ratings boost and a spot in the network’s lineup of must-see TV. Ending the show after five seasons was always Rae’s intention. “I pretty much go with my gut, and this is what my gut’s been telling me forever,” she says. The COVID has, naturally, made production harder. Extras for crowd scenes have to be quarantined together in a hotel. Episodes have to be shot out of order, and work hours have to be trimmed. Production also had to be shut down for two weeks after a background actor tested positive.
Those who love Issa Rae’s onscreen presence will be relieved to hear that she’s also lining up more film and TV roles. Issa Rae is now producing such a variety of things “Next up is Sweet Life” a docuseries in the vein of Laguna Beach and The Hills about Black 20-somethings living in L.A.’s tony Baldwin Hills neighborhood. The show was inspired by the 2007 BET series Baldwin Hills, which Rae loved. She is also producing an adaptation of “Nice White Parents” a quietly infuriating podcast about a public school in Brooklyn. She’s writing, producing, and starring in “Perfect Strangers” a story about a group of friends learning each other’s darkest secrets during a chaotic dinner party. And then there’s the second season of “A Black Lady Sketch Show” the Emmy-nominated series that Rae executive produces.