Issa Rae & Prentice Penny Announce the Insecure: The 10th Anniversary Tour, Coming to YouTube Theater on October 8, 2026

Writer, producer and actress Issa Rae is bringing the nostalgia of her hit HBO series, Insecure, to YouTube Theater in Inglewood, CA on Thursday, October 8, 2026. Hosted by Rae alongside Insecure showrunner Prentice Penny, the shows will celebrate the 10-year anniversary of the iconic television series. 

Ten years after the first season of Insecure premiered, Issa Rae and Prentice Penny recently celebrated the milestone with the launch of their podcast, BLOCC PARTY: AN INSECURE PODCAST. Now, as part of Insecure's 10th anniversary celebration, the duo is bringing the conversation to the stage for a live experience. Featuring special guest appearances by Yvonne Orji, Jay Ellis and Natasha Rothwell on select dates, the tour will give fans an intimate celebration of Insecure's lasting cultural impact through candid conversations, untold stories and unforgettable moments from the groundbreaking series. 

TICKETS: Tickets will be available starting with a Citi presale (details below) beginning on Wednesday, July 15 at 12pm local time. Additional presales will run throughout the week ahead of the general onsale beginning on Thursday, July 16 at 12pm local time at Ticketmaster.com 

PRESALE: Citi cardmembers will have access to presale tickets beginning Wednesday, July 15 at 12pm local time until Thursday, July 16 at 11 am local time through the Citi Entertainment program. For complete presale details visit www.citientertainment.com.