Did I Do That? Issa Rae Dresses Up as Our ’90s Faves for GQ—and It’s Pure Comedy

Issa Rae at Marie Claire’s Image Makers Awards 2018 on Jan. 11, 2018, in West Hollywood, Calif.
Photo: Phillip Faraone (Getty Images for Marie Claire)

Urkel. Moesha. The Fresh Prince. If you were a kid in the 1990s, at least one or all of the above were likely among your faves. We’re not sure if Issa Rae, who was born in 1985, grew up on these classic characters, but it sure gave us a laugh to see her dress up as each for the June issue of GQ magazine.


For what GQ calls “Hands Down the Best Comedy Issue Ever,” Rae also glamorously (and hilariously) appears on the cover, poking fun at Vanity Fair’s infamously photoshopped 2018 Hollywood issue alongside comedians Kate McKinnon and Sarah Silverman. Inside, she dishes on the much anticipated season 3 of her hit HBO show, Insecure, and reveals that she’s every bit as awkward as she once claimed to be:

“I do feel like people expect me to be entertaining,” Rae says. “And I’m not. I’m not an entertaining person. I don’t put on for anybody. I think about someone like Tiffany Haddish, who’s just naturally entertaining, who always has a story. And that’s just not my lane. I’m always gonna be the shy one.”

Screenshot: GQ.com

She may be shy, but Rae has proved again and again to be a gifted storyteller. Personally, we can’t wait to see what Insecure has in store for us when it returns Aug. 12. But before then, we’ll be looking forward to see what she wears to host the CFDA Awards—from the Council of Fashion Designers of America—on June 4.


The Glow Up tip: You can catch Issa Rae covering the June issue of GQ, on newsstands now.

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Maiysha Kai

Maiysha Kai is Managing Editor of The Glow Up and your average Grammy-nominated goddess next door. Minneapolis born, Chicago bred, New York built. Nuance is her superpower.