In 2011, The Mis-Adventures of An Awkward Black Girl, a comedy web series, introduced us to Issa Rae: the endearing yet glaringly awkward girl next door. The star slash producer slash director dazzled Hollywood with her infectious personality and her comedic capabilities (most of which involved her ability to poke fun at herself). Just five years later, Rae’s meteoric rise landed her at HBO with the hit show Insecure, the network’s first comedy in over four decades that was both created by and starred a Black woman — signifying the comedienne’s proclivity for making her mark everywhere she goes.
Following its debut, Insecure garnered massive acclaim for its remarkable depiction of real life uncomfortable experiences of the modern-day Black women (from tumultuous relationships and careers void of purpose to best friend drama). From the Inglewood complex, “The Dunes,” viewers gleefully watched Issa Dee (played by Rae herself), Molly (Yvonne Orji), and Lawrence (Jay Ellis) fumble through the cumbersome parts of adulthood with an enthralling humor that spanned across four seasons. As the comedy drama series nears its fifth and ultimately final season, Rae reflects on the end of an era in her latest cover interview with Vanity Fair. And although fans are dismayed to say farewell, Rae always intended for the hit show to conclude after five seasons.
Nodding to her intuition, she said, “I pretty much go with my gut, and this is what my gut’s been telling me forever.” Rae has been rewatching the early episodes and memories from the past rush in as she reminisces on the show’s infancy. “All these memories come up, so I can’t watch it purely objectively,” she said. “And then, of course, you look at performance stuff, you look at hair stuff, you look at appearance stuff. You’re just like, Okay, wow, I went on TV like that?” Over time, expansive budgets amped the beauty departments and even the scripts were composed with even more pensive monologues and scenes. As the show polished itself and reached new heights, the network even scheduled the show to air between primetime viewing like Game of Thrones and Ballers. The multi-hyphenate added, “I’m finding myself putting season-one pressure back on the show again.”
And of course, this isn’t the last we’ll see of Rae’s ingenuity, but for now, she’s pivoting to live primarily off-screen. Her upcoming projects include a Baldwin Hills-inspired docuseries titled Sweet Life, an adaptation of the podcast Nice White Parents, an Italian-based dramedy Perfect Strangers (which she’ll appear in) and the second season of the Emmy-nominated series A Black Lady Sketch Show. According to Vanity Fair, Rae is also reviving Matt Damon and Ben Affleck’s Project Greenlight on HBO Max. The docuseries, which was previously cancelled after Damon refuted the necessity for diverse casting of participants, will now center the next generation of promising female filmmakers who will be given the chance to direct a feature film. Looking forward to the show’s reinvention as a platform for overlooked talent, Rae said, “I want this version of the show to make filmmaking feel attainable.”