Issa Rae grew up in a family that moved around from Los Angeles to Senegal to Potomac, Maryland and back to Los Angeles. In some towns she was the only Black girl, in others, she felt a step behind from Black culture. It was the between-ness of not being definable, not quite fitting in, her awkwardness that served as her creative catalyst.
She was 11 when her family returned to LA. At the time, it was the golden age of sitcoms, with a series of breakout shows featuring Black casts including A Different World, Living Single, Moesha, and The Fresh Prince of Bel-Air. Those shows inspired her to make her own mark. That year, at age 11, she wrote her first spec script for the Bill Cosby sitcom, Cosby. While the rejection letter was swift, so was inspiration, this time in the form of Gina Prince-Bythewood’s debut film Love & Basketball further fueling her need to tell her story.
At Stanford, she created the YouTube web series Dorm Diaries, followed by Awkward Black Girl, The main character, J, was the prototype for Insecure’s Issa Dee: a socially awkward and uncertain young woman navigating work, friends and love, and often getting it wrong. With a growing fanbase, Season Two of ABG was funded by Kickstarter and Pharrell, who screened the series on his YouTube channel, iamOTHER. The series won the Shorty Award for Best Web Show in 2012. With new doors opening, she wrote an an unaired 2013 pilot called I Hate L.A. Dudes, produced by Shonda Rhimes. That ended up being an important lesson, as she was so intent on fitting in again, she lost focus of the story she wanted to tell from her unique lens.
Soon after, Rae teamed up with Larry Wilmore who became a mentor and a partner in developing Insecure (originally titled Non-Prophet). She wanted the show to be a real portrayal of what it’s like when you haven’t yet figured your life out.
Despite the numerous awards and accolades for Insecure, Issa Rae would likely say she’s still trying to figure it out. She still yearns to belong, aiming to be among the greats, names that roll off your tongue like Denzel Washington, Cicely Tyson, and Oprah. She’s well on her way. Aside from her work on the now acclaimed, breakout HBO series, Insecure (2016-2021), she’s co-owner of Hilltop Coffee with three locations around LA, has a hair-care company, Sienna Naturals, has partnered with industry giants with campaigns for Madewell, LinkedIn, American Express, Converse and more. Her biggest step in solidifying her name among the greats was the launch of her production company in Hyde Park Hoorae, overseeing the 22+ film, television, music, and events that Rae has in the works. Coming up, Hoorae will debut a reality show for HBO, Sweet Life, along with the fifth and final season of Insecure, set to air in late 2021.
Her Advice to Writers:
Find a Need and Service It: “I wanted to see Black women depicted on screen, but there was no diversity, no balance, no way to break in. So I decided to do it myself. Thanks to the internet, episodic TV seemed possible. There were more open doors,” she stated at a Sundance panel for TV writers.
She talks through her full list here.
Just start
Don’t lose your voice
Stop making excuses – you’re the only one stopping you
Create community
Be creative
Find your confidence
Be fully committed – If you don’t identify heavily with your material, you’re in trouble.
Embrace who you are – let go of not good enough, cool enough, etc.
Work with great people
Give great speeches
Perfect your pitch
Boss up. Be a boss bitch.