“It Feels Like Graduation”: 'THR Presents' Q&A With Issa Rae and Cast of 'Insecure'

Prentice Penny, along with Issa Rae, Yvonne Orji, and the cast of Insecure discuss the show's final episode.

“It Feels Like Graduation”: ‘THR Presents’ Q&A With Issa Rae and Cast of ‘Insecure’

Five months after the release of the series finale, the cast and creators of Insecure are back together. The group, including series creator and star Issa Rae, showrunner Prentice Penny, and castmembers Yvonne Orji, Jay Ellis, Kendrick Sampson, Amanda Seales, and Christina Elmore reunited for a THR Presents conversation (powered by Vision Media) dedicated to the end of their historic series.

“It’s like graduation, where you don’t miss high school necessarily but you miss the people,” says Rae. “And you can see how everyone went off to college, or is working. It’s a blessing for everyone to have a platform to go off and do their own thing afterwards.”

The group gathered virtually, one of the many creative pivots they’ve grown used to over the past two years. Insecure’s final season was, as with many Hollywood projects, complicated by strict pandemic protocols during the filming of its final episodes. “We had to make the show a completely different way than we’re used to,” says Ellis. “We’re a family and there are a lot of hugs on our set, a lot of popping into each other’s trailers, and all of a sudden that was taken away. So while we were still together and getting to make something beautiful, it happened in a way that felt foreign.”

The heightened stress of the pandemic “galvanized” the show’s creative team to end the stories of Issa, Molly, and the rest of their friend group in the right way, says Penny, who notes that they brought an extra level of intentionality and focus to the final episodes. For Sampson (Nathan), who in addition to his acting career is the co-founder of social justice organization Build Power, the time on the set of Insecure’s final episode proved an important lifeline. “I’ve thought about it a lot and there’s no group, no project, no work that I’d want to do during a pandemic, and in a situation with that heaviness, more than this group,” he says. “If it was run by white folks, I’m telling you I wouldn’t have made it through that project. And these actors, it ain’t even about us all being Black, it’s these people, this energy, I loved being able to go and spend time with you during that hard time.”

The majority of the cast — along with Penny — have been together since the HBO show premiered back in 2016, and have had a front row seat to its groundbreaking success, as it brought storylines of everyday Black life and love to TV screens and turned south Los Angeles businesses into well-known landmarks. Issa Dee’s first apartment building, The Dunes in Inglewood, has become a site of pilgrimage for the show’s dedicated fans, as have places like Worldwide Tacos and Pann’s Restaurant.

But to the team, one of the show’s most important legacies is simply the way they honored their characters, flaws and strengths alike. The finale, “Everything Gonna Be, Okay?!” used a series of flash-forwards to show how the characters’ lives progress: Molly (Orji) has a fairytale wedding (and honeymoon), Tiffany (Seales) expands her family and, in a decision five seasons in the making, Issa and Lawrence are finally together — and for good this time. In the above conversation, the group reveals the many conversations that went into choosing each characters’ final path, and what they’re each taking away from their time on the show.

This edition of THR Presents is sponsored by HBO.