Tuesday, July 14, 2026

Issa Rae Brings ‘Insecure’ Anniversary Tour to 13 Cities This Fall

“Insecure: The 10th Anniversary Tour,” a 13-date fall run led by Issa Rae and showrunner Prentice Penny, with Yvonne Orji, Jay Ellis and Natasha Rothwell scheduled for select appearances opens Sept. 10 in Philadelphia and closes Oct. 8 in Inglewood, California.
Ten years after Issa Dee first worked through her problems by rapping to herself in a bathroom mirror, Issa Rae is taking the stories, arguments and lingering questions of “Insecure” on the road.

Rae announced “Insecure: The 10th Anniversary Tour” on Tuesday, a 13-city run that will reunite her with showrunner Prentice Penny for live conversations about the HBO comedy that made awkwardness, friendship and the everyday lives of Black millennials worthy of prestige television.
 

The tour opens Sept. 10 at The Met in Philadelphia and travels through National Harbor, Maryland; Detroit; Boston; Brooklyn; Montclair, New Jersey; Las Vegas; Oakland; Chicago; Atlanta; Irving, Texas; and Houston. It closes Oct. 8 at YouTube Theater in Inglewood, California — the city whose neighborhoods, businesses and changing identity were central to the series.

Yvonne Orji, who played Molly Carter; Jay Ellis, who played Lawrence Walker; and Natasha Rothwell, who played Kelli Prenny, are scheduled to appear on select dates. Organizers have not announced which cast members will participate in each city, so ticket buyers should not assume the full group will appear at every stop.

The live shows are expected to feature behind-the-scenes stories, candid conversations and reflections on the series’ most memorable moments and cultural impact.

Rae announced the tour with a video built around a reunion of the cast’s group chat. After Rae proposes the idea, Ellis, Orji and Rothwell quickly sign on.

“It’s ‘Insecure,’ but we’re very secure now,” Orji says near the end of the clip.

“Come see us on tour,” Rae adds.
 

Created by Rae and Larry Wilmore, “Insecure” premiered on HBO in October 2016 and ran for five seasons before ending in December 2021. The comedy followed Issa Dee and Molly as they negotiated friendship, relationships, work, ambition and the consequences of decisions that often looked much clearer after they had already made them.

The show’s appeal came partly from what it refused to do. Its Black characters did not exist solely to explain racism, carry a social message or serve as flawless examples of representation. They could be selfish, funny, petty, accomplished, confused, loyal and painfully wrong — sometimes within the same episode.

“Insecure” also treated South Los Angeles as more than a backdrop. Restaurants, apartments, neighborhood businesses, art spaces and community events became part of the story as Issa tried to build a career without abandoning the place that shaped her.

Music was just as important.

The series used contemporary hip-hop and R&B as an extension of its characters’ inner lives, placing established artists alongside records that many viewers were hearing for the first time. Solange consulted on the first season’s music, while longtime music supervisor Kier Lehman helped build later soundtracks that included SZA, Jazmine Sullivan, Miguel, Jorja Smith, Leikeli47, Thundercat, The Internet, Dreezy and others.

Songs did more than fill transitions. They carried scenes after the dialogue stopped, helped define Issa and Molly’s emotional distance and gave each season a musical identity that fans discussed alongside the show’s romances and betrayals.
 

The anniversary tour extends a reunion that began in May with “Blocc Party: An Insecure Podcast.” The weekly rewatch series features Rae and Penny revisiting individual episodes, telling stories from the writers’ room and bringing in members of the cast and crew.

A Citi cardholder presale begins Wednesday at noon local time. General ticket sales begin Thursday at noon local time through Live Nation and Ticketmaster. Most listed performances begin at 8 p.m., and several venues identify the events as restricted to guests 18 and older.
The complete tour schedule:
  • Sept. 10 — The Met, Philadelphia
  • Sept. 11 — The Theater at MGM National Harbor, National Harbor, Md.
  • Sept. 13 — The Fillmore Detroit, Detroit
  • Sept. 16 — MGM Music Hall at Fenway, Boston
  • Sept. 17 — Brooklyn Paramount, Brooklyn, N.Y.
  • Sept. 18 — The Wellmont Theater, Montclair, N.J.
  • Sept. 25 — The Palazzo Theatre, Las Vegas
  • Sept. 26 — Fox Theater, Oakland, Calif.
  • Oct. 1 — The Chicago Theatre, Chicago
  • Oct. 2 — Tabernacle, Atlanta
  • Oct. 3 — The Pavilion at Toyota Music Factory, Irving, Texas
  • Oct. 4 — Bayou Music Center, Houston
  • Oct. 8 — YouTube Theater, Inglewood, Calif.
“Insecure” ended with its characters growing into lives that once seemed out of reach. A decade after the premiere, Rae is reopening the group chat.

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