Philadelphia gets opening night. Issa Rae’s Insecure: The 10th Anniversary Tour kicks off its 13-city run at The Met Philadelphia presented by Highmark on Thursday, September 10, 2026 — ahead of stops in Washington D.C., Detroit, Boston, Brooklyn, and seven more cities through early October. Ten years after Insecure premiered on HBO, Issa Rae is bringing the show’s cultural legacy to the stage, and Philadelphia is where it starts.

What the Insecure 10th Anniversary Tour Actually Is

The Insecure 10th Anniversary Tour isn’t a screening or a straightforward stand-up set. Hosted by Issa Rae alongside Insecure showrunner Prentice Penny, the tour extends their recently launched podcast, BLOCC PARTY: An Insecure Podcast, into a live stage experience — candid conversations, untold stories, and unforgettable moments from a series that helped define what specific, grounded portrayals of Black womanhood and friendship could look like on television. Insecure launched Issa Rae into a genuinely major multi-hyphenate career as a writer, producer, and actress well beyond the show itself, which is part of why a 10th anniversary tour built around it carries real weight rather than reading as pure nostalgia marketing.

The biggest draw beyond Rae and Penny: special guest appearances by Yvonne Orji (Molly), Jay Ellis (Lawrence), and Natasha Rothwell (Kelli) on select dates throughout the tour. Philadelphia’s specific guest lineup for opening night hasn’t been confirmed as of this writing — worth checking official tour updates closer to September 10 for exactly who’s joining that first show.

Insecure 10th Anniversary Tour Tickets and How to Get Them

Citi cardmembers get first access through a presale running Wednesday, July 15 at noon through Thursday, July 16 at 11am, via the Citi Entertainment program. General on-sale opens Thursday, July 16 at noon at Livenation.com. Additional presales run throughout the week ahead of the general sale — worth checking Live Nation directly if you’re not a Citi cardmember and want a shot before Thursday.

Ten years since Insecure first aired and the Insecure 10th Anniversary Tour is finally arriving, Philadelphia gets first crack at whatever this live version of the show turns out to be. That alone is worth marking September 10 on the calendar.

About Post Author

Allan Lane

Philadelphia born and bred, Allan Lane is the Publisher and Editor in Chief of digital magazines. He launched his first publication, SportBikes Inc Magazine in 2010, followed by dosage MAGAZINE in 2019. Recently, Allan launched his third online publication, Club For Man. As a journalist, Allan covers fashion, lifestyle, culture, art, and motorcycles.

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