From 'Awkward' to A-List! How Issa Rae Turned Her Hit Youtube Series Into HBO's Hot New Show - And What Her Mom Says of Those Sex Scenes

Photo: Jason LaVeris/FilmMagic

She may be known for being hilariously unsure of herself, but Issa Rae is actually pretty confident these days.

Thanks to Insecure, her bitingly smart, semi-autobiographical HBO show, back for its second season, the creator, writer and star is feeling more secure than ever. “I’m doing what I love with who I love and I feel good at it,” she tells PEOPLE in this week’s issue, opening up about her amazing journey.

The only thing she’s not too sure about is her mom Delyna watching the show. “I don’t think she should watch this season,” she says, eyes widening like those of her self-conscious character, also named Issa. “She hates cursing and didn’t let us watch R-rated movies until we were 17.” With two sex scenes in the season premiere episode alone, the show—which follows Issa and best friend Molly‘s millennial misadventures with work and relationships in Los Angeles—is set to be even racier.

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After Delyna’s friends watched Insecure‘s first season, “My mom said, ‘They’re embarrassed for me!'” says Rae, to which she responded, “‘I don’t know what to tell you, Mom—I didn’t make the show for them. I’m sorry!'” But there’s no apology necessary for Rae’s legion of fans, many of whom first met her online.

For more on Issa Rae’s journey to TV stardom, pick up this week’s issue of PEOPLE, on newsstands now.


The Los Angeles bred, Stanford-educated star, 32, first found fame with her popular YouTube series The Misadventures of Awkward Black Girl, in which she wrote, directed and starred. Episodes often showed Rae’s funny attempt to navigate uncomfortable run-ins with her black and white co-workers and love interests. It amassed a huge number of views and young followers but also caught the attention of TV executives, affording Rae the opportunity to bring her raw and unique comedy to the small screen.

“Issa is the younger version of me if I didn’t know what I wanted to do, or if I cared as much about relationships as she does,” says Rae of her character. “But our personalities are similar for sure.”

From PEN: Issa Rae’s Relationship Comedy ‘Insecure’ Continues Its Hot Streak In Season 2

The real Issa picked up her sense of humor as a child. Born Jo-Issa Rae Diop to Delyna, a teacher from Louisiana, and dad Abdoulaye, a pediatrician from Senegal, Rae says, “Out of the five siblings, I’m the least funny.” She recalls mandatory sit-down dinners at the Diop household feeling like episodes of Last Comic Standing.

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Courtesy Issa Rae

Though she originally planned to follow in her dad’s doctor footsteps, Rae realized in high school medicine wasn’t for her. “My dad was like, ‘I’m hurt, but you can still be a lawyer!'” she says, joking that he was horrified to learn she’d majored in African-American studies at Stanford. “He was like, ‘You might as well have majored in flowers!'”

But she credits Stanford with helping her find her calling, and for giving her lifelong friends (some of which she bases her characters off of). “All of the people I met there are just incredible,” she says, noting that her pals all chipped in when she was struggling to finance new episodes of Awkward Black Girl. “They’ve just supported me no matter what.”

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Courtesy Megan Lawson

For Rae, who grew up watching Family Matters and was a huge fan of the show Girlfriends, starring Tracee Ellis Ross,it’s always been her dream to bring true-to-life black female relationships to television. Having picked up a Golden Globe nomination earlier this year and now rumored to be writing an upcoming Ava DuVernay project starring Rihanna and Lupita Nyong’o, Rae has hit her stride.

“The biggest insecurity for me now,” she says, “is what do I do next?”

Insecure airs Sunday nights at 10:30 p.m. on HBO.

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