From 'Fresh Prince' to Drake

By Ray Rahman
Updated October 04, 2016 at 12:00 PM EDT
Credit: John P. Fleenor/HBO
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Ever since her web series The Misadventures of Awkward Black Girl debuted back in 2011, Issa Rae has been one of comedy’s freshest, most intriguing voices. In her upcoming HBO series, Insecure, the 31 year old takes that talent and wit to the next level as star, writer, and EP and serves up a story that borrows from her own experiences navigating race, relationships, and career. (Hint: Even when you’re a best-selling author and buds with Larry Wilmore, life is still awkward.) The Los Angeles native filled us in on the pop culture touchstones, from Fresh Prince to Drake, that have helped shape her TV debut.



Nineties black TV influenced me — all those shows made me feel like, “Oh, I can do it.” A Different World made me want to go to college. Seeing black people in college was really cool; it was just a different dimension to us. I loved Fresh Prince and Living Single for their comedy and wanted friends like [the characters]. I can really identify with Will Smith; he was like the Everyman in a great way that I hadn’t seen a black person do before. That block of television, just a bunch of black people on TV, made me want to write for those characters specifically.


I think seeing Tina Fey in general as just this kind of quirky, uncomfortable, self-deprecating woman who was just hilarious. She was deadpan in a way that reminded me of Daria, which just cracked me up. I remember thinking like, “Oh my gosh, I identify with this woman so much, and I wish we had our own version.”



It was the first movie I saw that was set in my neighborhood — just regular black people living life, which is kind of what we’re trying to do with Insecure. Seeing my neighborhood in that light…that was really cool, and I remember wanting to do that in my own work.




We used to have a Drake lyric in every episode of Awkward Black Girl. It was my own personal Easter egg. He has a way of being the soundtrack to my life. It’s just something where with every album and every song, I can pinpoint where I was driving or what was going on in my life and how that song is speaking to me and my own emotions, and I just love that about him. He has a real knack for knowing what’s going on, kind of like a music psychic.


It took me a while to embrace her because I was a prude child. I was kind of goody-goody, and her lyrics were mad nasty. Now I find myself fast-forwarding 20 years later with the most pottiest of mouths, with a show that doesn’t hold back in terms of how women talk to each other and how we talk about sex.

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Her books make cameos throughout [Insecure] just because I love how her main protagonist is a dark-skinned black woman. You’ll see that there are two dark-skinned black leads in this show, something that hasn’t been done much as a comedic duo. She has a great voice and a way of telling stories that feels so raw, so real, and she uses a lot of research to make you feel like, “Oh, am I reading fiction or am I reading nonfiction?”


I remember reading her book, Is Everyone Hanging Out Without Me? It was the first time I read an autobiography and was like, “Oh my gosh, I know this girl. I am this girl.” And she’s also been an amazing supporter, too, in terms of encouraging Awkward Black Girl and my own book and expressing excitement to see Insecure.


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