These Insecure Cast Then Vs. Now Photos Prove A Lot Can Change In 5 Years

Co-created by Issa Rae and based on her acclaimed Awkward Black Girl web series, HBO’s Insecure has explored the modern Black experience through late-20s Los Angeles natives and best friends Issa Dee (Rae) and Molly Carter (Yvonne Orji).

Thanks in part to its Emmy, Peabody, and three NAACP Image Awards, the comedy series has catapulted its stars to A-list status over its five-year run. Insecure is about to come to an end, but as Season 5 rolls out, here’s how each cast member has changed since Season 1.

Besides Awkward Black Girl, Rae created and produced several films and series before Insecure. Prior to its 2016 premiere, she told the TCA, “We’re just trying to convey that people of color are relatable. This is not a hood story. This is about regular people living life.”

Since 2016, Rae has acted in films, including Little, The Photograph, and The Lovebirds. She currently produces HBO’s A Black Lady Sketch Show and Sweet Life: Los Angeles, created the network’s upcoming Rap Sh*t, and will appear in the Spider-Man: Into the Spider-Verse sequel.

Orji hadn’t done much acting when she booked her breakthrough role as the free-spirited Molly. A devout Protestant in real life, she said in 2016, “Once I read the script, I remember calling Issa, and I said, ‘Issa, Molly is who I would have been if I didn’t get saved at 17.’”

Insecure launched Orji’s career in full force, and she’s since appeared in the films Night School, Spontaneous, and Vacation Friends. The Nigerian-born actress is currently developing a biographical series for Disney+ titled First Gen, produced by Oprah Winfrey and David Oyelowo.

Jay Ellis plays Issa’s on-again, off-again boyfriend, Lawrence. Insecure marked his second main TV role following Bryce “Blueprint” Westbrook on The Game. On Insecure’s true-to-life dialogue, he told HBO, “That’s how people around me live, talk, speak and interact in the world.”

Ellis has since nabbed more high-profile acting roles in films, like In A Relationship, Escape Room, and Top Gun: Maverick. He earned his first producer credit on Amazon’s 2020 horror Black Box and will star in Dave Franco’s upcoming directorial debut, Somebody I Used to Know.

Natasha Rothwell had worked as a Saturday Night Live writer prior to joining Insecure as Kelli Prenny. “I’m very much the antithesis of Kelli. When people meet me, they’re surprised to learn that I express my confidence in a more subdued way,” she told GQ.

Rothwell has since acted in Love, Simon, Like A Boss, Sonic the Hedgehog, and Wonder Woman 1984 and earned praise for her role as Belinda on The White Lotus. She’s also struck development deals with both HBO and ABC and will act in the upcoming Wonka starring Timothée Chalamet.

Before scoring the role of Tiffany DuBois on Insecure, Amanda Seales had performed since her teen years, released several hip-hop EPs and mixtapes, and acted in Nickelodeon’s My Brother and Me. But the hit HBO series has propelled her to a new echelon of stardom.

She's since released her first comedy special, I Be Knowin’, and hosted The Real, the 2020 BET Awards, and game show Smart Funny & Black. “I get to sing, host, use my master's in African-American studies, and do comedy,” she said. “This is the realization of a dream.”