While Issa Rae had been acting for some time before “Insecure,” the HBO series is arguably what skyrocketed her into the mainstream. But perhaps even more significant was the effect that Rae’s earnest mission for authentic representation had on audiences. 

Acting as a spiritual successor to Rae’s hit web series “Awkward Black Girl,” “Insecure” follows Los Angeles native Issa Dee (Rae) as she navigates the trials and tribulations that come with her late 20s and early 30s alongside her close friend Molly (Yvonne Orji). While the show dives into real-world dilemmas affecting the Black community from gentrification to the racist nature of microaggressions, Rae’s ultimate goal with the series was to depict Black people in honest and flawed ways. 

“I thought it was massively important, not just for African Americans but just generally for black women all over the world, to see ourselves portrayed so normally,” Rae stated in an interview with The Guardian. “‘Insecure’ shows the humdrum experiences that all black millennial women go through … It just hits this sweet spot that quite a lot of predominantly white shows allow their characters to exist in, which is to be realistic, complex and live outside of the stereotypes.” 

That genuine mission resonated with countless individuals as “Insecure” became a major success. The show ran for five seasons, ending in 2021 with 13 Primetime Emmy nominations including three for Rae’s performance and one for outstanding comedy series. It wouldn’t be Rae’s last time working with HBO, as she later executive produced and guest starred in episodes of the sketch comedy “A Black Lady Sketch Show.”