Issa Rae built an empire of awkward, but she’s still not satisfied

Issa Rae spent her youth feeling awkward, and she’s never gotten over it.

She spent her early years in Senegal, where her father was from, before moving to the suburbs of Washington, DC. “Coming from West Africa to Potomac, Maryland, was pretty jarring," she says. "I just didn’t know how to be black."

She felt like a token minority at school, and her older brothers would tease her: “'You’re kind of a white girl, a Jewish girl.'" Things didn't improve when she went to a predominantly black school in Los Angeles. She didn’t know how to fit in there, either.

But those awkward interactions were formative for Rae — and they were comedy gold. She channeled them into sketch comedy, uploading videos she made with her friends to YouTube. The first episode of her web series, "The Misadventures of an Awkward Black Girl," made her an Internet star in 2011.

(Just as a warning, nearly everything Rae does features profanity.) 

The videos don’t have the best production values, but their authenticity struck a chord. Pharrell Williams’ i am OTHER YouTube channel picked up — and funded — the second season of the series. “He completely got it,” Rae says of Williams, who claimed the he himself was an awkward black guy.

“He was extremely supportive of the vision and making sure that nothing was changed,” she says. That support, coupled with an actual budget, made for episodes that looked a lot better and got millions more views. 

Her first experience with network TV was at ABC, where she pitched "I Hate LA Dudes" with the help of producer Shonda Rhimes. “Working with them was amazing, but I felt like I was a pushover,” Rae remembers.

ABC passed on the idea, but she’s been developing a pilot with HBO that would be the first series on the network starring an African-American woman. "Non-Profit" is about a directionless twentysomething who works for a non-profit by day and aspires to be a rapper by night.

You could say it's kind of a black take on "Girls," the hit HBO series. Lena Dunham’s show was criticized for not including characters of color, but Rae isn’t judgmental about the show. “Those are her friends, those are the stories that she knows," she points out. "That’s authentic to her."

Rae argues that TV should instead work to develop shows with similarly authentic views on different cultures. "What I want to see is just varying experiences, not just white people’s experiences," she says. "And I think that’s entirely possible. We had an era of it for a while [including Living Single and Fresh Prince], and then we didn’t.”

Rae is working to usher in that era, and not just with her own shows. She launched ColorCreative.TV, a incubator for web series that produces pilots and is focused on “increasing opportunities for women and minority TV writers.”  She’s also helped launch The Choir, a dramedy about rebuilding a dying congregation; Roomieloverfriends, a comedy about hooking up with your roommate; and First, a romantic saga about a young couple.

So Rae isn’t just awkward anymore: She’s made herself a mogul of awkwardness. But even that isn’t enough. Rae hasn’t even begun to working on her dream job. “I want to tour the world doing hood rat music with my friends," she says. Then she drops the most awkward verse in the history of rap. 

This story is from Sideshow, a new podcast from PRI's SoundWorks network hosted by Sean Rameswaram that looks at the intersection of culture and technology.