From ‘Awkward Black Girl’ to star of ‘sharpest comedy of the year’

For someone who was just dreaming of attending the Golden Globe Awards last year, and then showed up as a nominee at the event early this year, Issa Rae has no reason to be “Insecure.”

Time magazine recently paid Issa Rae and her HBO show, “Insecure,” the highest compliment: “Last year, the first season of ‘Insecure’—the HBO series cocreated by and starring the magnetic comic Issa Rae—was among a constellation of bright spots … The series introduced a sharp, fully formed perspective on the world, one from outside the class of comics (often white men) who historically gets the chance to create its own half hours.

“In its second season, which debuts on July 23, ‘Insecure’ stands on its own as the sharpest comedy of the year … Rae’s performance is incandescent and would make for a worthy choice to award should Emmy voters decide that Julia Louis-Dreyfus has collected enough hardware.”

“Insecure” was partially based on “Awkward Black Girl,” Issa Rae’s award-winning web series that debuted on YouTube in 2011. The show went viral and caught the attention of Pharrell Williams, who partnered with her in Season 2 and showed it on his YouTube channel, i am OTHER.

The Los Angeles native next worked on a comedy series pilot, which HBO picked up and was eventually titled “Insecure.”

The daughter of a pediatric doctor and a teacher, Issa Rae graduated from Stanford University with a major in African and African-American studies. She headed next to New York when she received a fellowship at The Public Theater.

Issa Rae is reportedly going to write a buddy comedy starring Rihanna and Lupita Nyong’o, to be directed by Ava DuVernay.

Excerpts from our talk with Issa Rae, who was statuesque in a pink off-shoulder dress by Lavish Alice:

How confident, less insecure have you become? Knowing what I want to do professionally has helped, just in my journey to pursue television and film writing. The feeling like that [career] is coming along definitely adds to my confidence. My personal life is trash and a mess, but I’m getting there. I’m learning.

What do you think makes men insecure? Public failure is a big thing for men. I read somewhere that in a survey, men’s biggest fear was being …

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