Cheryl “Salt” James: I remember Issa creating a Kickstarter account in 2011 to raise money so she could finish the first season of her YouTube series “The Misadventures of Awkward Black Girl” (2011-13). That always struck me as savvy and bold. I had the privilege of watching her build her audience, then take them with her to HBO for “Insecure.”
When you’re an artist, people are always questioning your vision. Ideas can get stretched and pulled in different directions, and they can become diluted. Issa has always, from what I can see, followed her gut.
Sandra “Pepa” Denton: In her memoir [2015’s “The Misadventures of Awkward Black Girl”], Issa mentions struggling with not feeling Black enough. I can relate to that. When Salt-N-Pepa was selling millions of records, they called us “crossover,” which meant that we weren’t Black or hip enough. Now everyone wants to be pop. It means you’ve gone global. Like us, Issa stayed strong and was smart about her struggle, turning it into comedy. She kept it real, too.
Issa Rae: I grew up on Salt-N-Pepa. I’ve always admired their collaboration as partners and the way they complement each other. It’s so hard for a group to last in this business, but they continue to be unapologetic about who they are and what they’re about. So much of my inspiration as a writer comes from female rappers. I write to rap music. When I was in middle school, I even tried to start rap groups because of Salt-N-Pepa. I had no business doing that, but they made me think I could.
I found my voice as an artist when, as a teenager, I realized I could tell stories that either made people laugh or feel something. With my web series “The Misadventures of Awkward Black Girl,” there’s so much of me on camera — my sensibilities and sense of humor are on full display — and having the validation of that being what launched my career was both so scary and fulfilling. It took me a while to realize that it was my voice I was introducing to the world.
Interviews have been edited and condensed.
James’s and Denton’s hair by Yusef for the Wall Group. James’s makeup by Kasha Lassien for the Wall Group. Denton’s makeup by Mylah Morales for Six K. Rae’s hair by Felicia Leatherwood. Rae’s makeup by Joanna Simkin for the Wall Group. Production: Peter McClafferty. Tailor: Viktoria Gokun. Hair assistant: Diamond Brown
