At YouTube Theater in Inglewood, California, last night, the Insecure 10th Anniversary reunion brought Issa Rae, Yvonne Orji, Jay Ellis, Natasha Rothwell and showrunner Prentice Penny back together, with the series’ past still feeling as fresh as ever. The evening served up some of the show’s most memorable music, favorite characters and actors and a special reading of an episode that never quite made it to air.
The night felt like a gathering of old friends you haven’t seen in a while, but still remain close, as the cast laughed and loved together, answered some of the show’s biggest questions and remembered a time in their lives that felt unparalleled. Here are some notable moments from the reunion that everyone is talking about.
Issa Rae Raps About Broken Pu**y
Taking us right back to the first episode of Insecure, Issa Rae performed “Broken Pu**y” at an open mic night over an instrumental track of Kelis’ “Bossy.” The song is about her best friend Molly (played by Yvonne Orji), who struggles to keep a boyfriend. Of course, hashing out your friend’s man troubles — especially in public — is always gonna come back and bite you in the … behind, which is what does for Issa a few episodes later. But on this night, everyone was vibing to the beat, with each cast member coming out with their own headlining hit. Warning: These songs are definitely NSFW.
@buuutwhy It was so much fun! Loved seeing everyone that played a part to make Insecure such a memorable show! #issarae #yvonneorji #insecure #inglewood #comedy @HBO ♬ original sound – Nat
@mmcn_117 TOO LITTTT #insecurehbo #yvonneorji #youtubetheater #issarae #prenticepenny ♬ original sound – M
Surprise guests abound
After the Insecure tour was canceled, Rae promised the one-night-only reunion would be epic. And it was. The night included series and guest stars Natasha Rothwell, Kendrick Sampson, Christina Elmore, Sarunas Jackson, Neil Brown Jr., Wade Allain Marcus and more. The breadth of the cast meant some of the series’ biggest questions could be answered. And they did: Rothwell’s Kelli getting tased; who was in an open marriage, just to name a few. Yup, it all got laid out.
@blackboywrites Insecure 10 year reunion. 🖤 #insecurehbo #issarae ♬ original sound – Mike Gauyo
An alternate original ending?
We know how Insecure ended… or did we? At the reunion, the cast did an alternate table read for the series’ finale, which was how the series was going to end, but Rae and Prentiss decided to change it two weeks before the finale started shooting. Rae later shared that having the characters travel to Morocco felt a little too fantastical, so they changed it to a more grounded, authentic Los Angeles time jump. In last night’s table read, it was revealed that Issa Dee ended up with Nathan (Kendrick Sampson), and they had a baby, giving the Nathan hive the closure they so desperately craved. Lawrence (Jay Ellis) got a new girlfriend and Condola (Christina Elmore) got a new man, while she and Lawrence co-parent Elijah. Would this have been a more satisfying ending for the series than the one that aired on December 26, 2021? Fans can hash it out.
@be_euniqueee 10 years of Insecure ✨ The tour was cancelled… but LA still got a reunion show
Watch all five seasons of Insecure on HBO.