HBO’s ‘Insecure:’ Issa Rae Takes Charge

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HBO’s ‘Insecure’ star and co-creator Issa Rae experiences relationship and personal drama along with her on-screen best friend Yvonne Orji (Molly). (Photo Credit: Anne Marie Fox for HBO)

Issa Rae used to mask her online addiction from her peers. The then-teenage budding tech junkie cut her teeth frequently logging on AOL, creating identities and instant messaging. By the time social media became immensely popular in the mid-2000s, the now 31-year-old Los Angeles native and creator behind the massively successful 2011 web series The Misadventures of Awkward Black Girl grew comfortable with embracing her online presence.

“Facebook was really my biggest addiction,” a radiant Rae recalls, joking that she refuses to have Snapchat. “It made it okay to be online and talk to your friends. It was really nerdy, and nobody was really doing it yet. I realized people enjoyed me being me.”

Rae’s silly status updates, in-your-face commentaries and microblogs eventually paid off: allowing The Misadventures of Awkward Black Girl, Rae’s third web series attempt overall, to net over 200,000 subscribers and 25 million views on YouTube. The actor, writer, director, editor, best-selling author and producer is gearing up to air her eight-episode, half-hour HBO comedy series, Insecure. The show, starring Rae, chronicles two African-American females experiencing relationship drama, personal growing pains and friendship conflicts.

Insecure’s origins date back to 2012 when the cable network approached the sought-after creative born Jo-Issa Rae Diop about potential show ideas. Rae landed an opportunity in 2013 to develop a series, I Hate L.A. Dudes, for ABC with showrunner Shonda Rhimes.

The broadcast channel passed on the pitch, so Rae took matters into her hands. The ambitious content curator created imprints, Issa Rae Productions and Color Creative TV, as incubators for women and minorities of color to showcase and potentially monetize their intellectual property absent of Hollywood’s approval.

Never one to condone “crabs in a barrel,” Rae aspires to help other creatives live out their dreams. “I want to see more of our stories,” the meticulous Stanford and New York Film Academy alumna says prior to a screening of Insecure during this year’s BronzeLens Film Festival in Atlanta. “I want to hear about more experiences that I haven’t had. I want to see that played out onscreen.”

Rae, with her arms and legs crossed, illuminating pearly Colgate smile and auburn pompadour braided hairstyle, adds, “Nobody wants to be the only one out there doing and telling stories. That’s not how you build as a community. That’s just not how I was taught to operate. I don’t want to operate that way.”

The Shorty award winner and Sundance Film Festival semifinalist lists Jerry Seinfeld, Larry David, Tina Fey, Donald Glover, Sinbad, Ellen DeGeneres, Chris Rock and Dave Chappelle as her muses. The massive success of Awkward Black Girl allowed Rae opportunities to produce digital content for Tracey Edmonds and Pharrell Williams.

The web trailblazer confirms that those working relationships are moments she patterns her career after. “They’re all bosses in their own right,” Rae says. “They have a firm brand, vision and solid voice. Those are all attributes that I need to feed off of. They taught me to be firm in who I am, the stories I want to tell, be confident that I’m supposed to be here and not let anyone convince me otherwise.”

Born the middle of five children, Rae, who was reared briefly in Senegal and Maryland during childhood, actually draws inspiration from her family. Rae’s relatives, she says, act as a focus group for her material.

“That’s where you test your comedy,” a delicate-voiced Rae declares. “That’s where you get your defense mechanism and quick comebacks. You just have to be on your toes with them. They’re some of the funniest people I know.”

Rae is not a fan of asking for help, but she acknowledges other contributors to Insecure. Whenever she mentions her creative partnerships on Insecure, Rae’s pitch goes up an octave. She co-creates, co-writes and co-executive produces Insecure with former Nightly Show host Larry Wilmore. Rae was devastated when the humorist took his post on Comedy Central: pinpointing how his influence proved infectious.

“I didn’t think anyone would be able to replace [Larry] and still nobody has,” Rae says. “He helped me to be firm and confident in my voice because he’s so firm and confident in his.” Insecure’s showrunner Prentice Penny grew up in the same neighborhood as Rae. Much like Rae’s character, the NAACP Image award nominee and writer/producer of the Fox police comedy Brooklyn Nine-Nine worked for a nonprofit.

Penny’s shared experiences with Rae is also instrumental in fueling the writing on Insecure. “He’s such a good storyteller,” she comments, “…such a smart man who’s very encouraging in terms of making sure that my voice was shown through these eight episodes and throughout the series.”

Solange Knowles is Insecure’s music consultant for the soundtrack. Grammy-winning music video director Melina [Matsoukas], famous for her work with Beyonce, Snoop Dogg, Whitney Houston, Rihanna, Lady Gaga, Katy Perry, Calvin Harris and Missy Elliott, made her directorial debut for a television series: directing four of Insecure’s episodes.

Referring to Melina as “the most vivid, thorough creative director,” Rae describes her fellow visual artist’s work ethic. “She will handpick extras down to the details, shoot something and choose the wallpaper,” Rae says. “Everything matters. To have her execute this show in such a way that I didn’t imagine and pretty much elevated is just an honor.”

Consistency and perseverance are what Rae believes are her greatest assets. Just before the screening at BronzeLens, she mumbles and chuckles under her breath how she hopes audiences enjoy and appreciate Insecure. Reiterating how important it is to be assertive and constantly working in visual media, Rae leaves some encouraging words that she hopes will encourage others to write and develop content they can be proud of.

“Know the story that you want to tell,” she says. “I was certain that I didn’t want to compromise my voice, so it helped me just be me.”

Insecure premieres on HBO on Oct. 9 at 10:30 p.m. EST. Check local listing for channel selection.

This post was written by Christopher A. Daniel, pop cultural critic and music editor for The Burton Wire. He is also a visiting instructor in the Department of Communication at Georgia State University. Follow Christopher @Journalistorian on Twitter.

Follow The Burton Wire on Twitter or Instagram @TheBurtonWire.

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