Legend Making Legends: Issa Rae Continues Creating Real Stories For The Culture & Putting The Girls On

The Daily Grind Video


Source: Amanda Edwards / Getty

This week we reintroduced you to living legend Larry Wilmore for his amazing contributions to the television and film industries. Wilmore is one of entertainment’s leading executives and the reason many other Black creatives like Issa Rae have been able to put countless other filmmakers in position. Here’s how one legend helped forge the path for a new legend named Issa Rae.

Wilmore remembers the moment his manager asked him to meet with an aspiring writer and filmmaker named Issa Rae in late spring 2013. At the time, he recalls being unaware of her buzzing web series “The Misadventures of Awkward Black Girl.” Wilmore did his research and says, “it was one of those ‘fall in love at first sight’ type of things” He instantly recognized her greatness and the potential within her existing lesser-known web series.

The two hit it off the first time they met with constant laughs and what Wilmore refers to as a “creative flirtationship.” Wilmore liked her so much and saw her vision for the future. They went on to collaborate on Issa’s breakout role as both the co-creator and star on HBO’s hit series “Insecure.”

“HBO was looking for me to possibly supervise her project,” Wilmore tells Indie Wire. “As somebody who had a lot of TV experience, to lend her a supervisory role. At the time, I wasn’t really doing anything, and I said, ‘Hey, do you want to just write this together? I’d like to just collaborate with you.’ We had one of the most fun summers just working on this project together, and hanging out and figuring out what the show was going to be.”

Since the culturally impactful show, Issa has managed to launch her own production company with HOORAE, release her second TV series “Rap Sh!t,” star in films like The Photograph, and continuously push the envelope by telling authentic stories for the Black community.

The Photograph

Source: NBC Universal / The Photograph

Rae’s contributions to the TV industry has elevated everyone around her from her co-stars, Jay Ellis, who portrayed her long-time lover Lawrence on “Insecure,” Yvonne Orgji, Natasha Rothwell, Kendrick Sampson and more. Not only is she a force onscreen, but similar to Wilmore, Issa has established herself as a boss offscreen too.

Insecure season 5, episode 4

Source: Merie W. Wallace / HBO

“She comes fully formed as an experienced writer,” Wilmore adds in the interview. “Not just somebody who has talent. It’s very rare.”

The gifted executive has had the best luck when forming a team around her. From working with the greats like Wilmore to her “Insecure” showrunner Prentice Penny, Rae has learned from some TV heavyweights who align with her mission to tell real stories centered around real and relatable characters. Something both executives Wilmore and Penny have been able to do with their own storytelling and continue in their current projects.

Premiere Of HBO's

Source: Amanda Edwards / Getty

“I’ll put it like this: I didn’t have what she has when I was at that stage,” Wilmore shares of his admiration for Rae. “It took years to develop some of those traits. That’s why I’m very much in awe of it and that type of thing.”

Wilmore even compares Rae’s talents to that of Oprah Winfrey saying, “I find her a mini-Oprah in some ways because she has this entrepreneurial quality about her where she’s just fierce in terms of her work ethic and how she views the business.”

Rae has been able to empower other young Black women with her own success. Her “Rap Sh!t” showrunner and co-executive producer Syreeta Singleton is now taking the industry by storm. Singleton formed a relationship with Rae during her time as a writer for “Insecure.”

Singleton is just one of the many Black artists’ lives Issa has been able to influence on their journeys. Rae continues to shine a light on new talent like Aida Osman, KaMillion and Jonica Booth who star in her latest comedy series “Rap Sh!t.” Independent artists like Kari Faux, Baby Tate, and more have also witnessed the impact of Rae’s bright light. Issa’s brings artists up as she soars and uses her passions outside of TV to uplift the arts community.

HBO Max Rap Sh!t Miami Screening Event

Source: Alberto Tamargo / Getty

“She’s not just an actress or even a writer,” Wilmore declares. “She really is an executive to be reckoned with.”

We know that’s right and Happy Black History Month! Thanks to Issa Rae for being a young legend making legends.

Issa Rae's MasterClass

Source: Courtesy of MasterClass / Courtesy of MasterClass