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Issa Rae Built a Hollywood Career on Her Own Terms. Next, She’ll Build an Empire

The YouTube and HBO star is as talented as she is ambitious

It’s a Friday afternoon in late August, and Issa Rae—the creator, star and executive producer of HBO’s Insecure—is leaving the bar at The London hotel in midtown Manhattan. But before she can make her way back to her room, a nervous woman stops her. Apologizing, the woman says that she never asks celebrities for photos, but on this particular occasion, felt compelled to make the effort.

A few moments later, after Rae has obliged the selfie request with a wide grin and left to get ready for a party for Insecure’s Season 2 soundtrack, the woman explains: Rae, she says, is “a hero for women 25 and up with melanin.”

Rae, 32, didn’t find this kind of recognition overnight. Sure, she created a beloved YouTube show in 2011 that was viewed by millions (Awkward Black Girl), landed a deal with ABC and Shondaland in 2012 (the network eventually passed on her show, I Hate L.A. Dudes) and in 2015, published a New York Times best-selling memoir (The Misadventures of Awkward Black Girl). But she’s also dealt with development hell: while with ABC, Rae says, she was unsure of the story she wanted to tell and overly eager to please executives, leading to “a mushy, generic script.”

After the ABC deal ended, HBO called Rae to tell her they liked her YouTube show and wanted her to pitch something in that vein. She did, creating Insecure, a half-hour comedy that follows “Issa Dee” and her best friend Molly as they deal with dating and job struggles in Los Angeles. HBO ordered a pilot in February 2015, and the series premiered in October 2016.

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