Comedian Dave Chappelle to headline Summerfest


The latest American Family Insurance Amphitheater headliner announcement comes with a twist as the new major act for the Big Gig isn’t a musician but a comedian: Dave Chappelle, who will perform a one-night-only show on Saturday, Sept. 11.

Chappelle last performed in Milwaukee in March last year at The Pabst Theater – some of the last live shows in the city before the COVID-19 pandemic shut the globe down. This will mark his first performance ever at the Big Gig, and perhaps the first-ever comedy headliner on the main stage. (NOTE: George Carlin famously performed in 1972, but as an opener for Arlo Guthrie, and Bob Hope headlined in 1969, but at County Stadium, before Summerfest had a permanent home.)

Tickets for the show will go on sale starting Friday, June 11 at noon at both Summerfest’s website and Ticketmaster. An advance warning: Cell phones, cameras and other recording devices will not be allowed into the Chappelle headliner show. 

With today’s announcement, the Summerfest headliner lineup is almost complete. Here’s where it stands now:


  • Wednesday, Sept. 1 – Green Day, Weezer and Fall Out Boy
  • Thursday, Sept. 2 – Luke Bryan
  • Friday, Sept. 3 – Chance the Rapper
  • Saturday, Sept. 4 – TBA
  • Wednesday, Sept. 8 – Jonas Brothers
  • Thursday, Sept. 9 – Chris Stapleton
  • Friday, Sept. 10 – Zac Brown Band
  • Saturday, Sept. 11 – Dave Chappelle
  • Wednesday, Sept. 15 – Dave Matthews Band
  • Thursday, Sept. 16 – Megan Thee Stallion
  • Friday, Sept. 17 – Miley Cyrus
  • Saturday, Sept. 18 – Guns n’ Roses

For more updates on Summerfest – and the rest of the summer festival season – stay tuned to OnMilwaukee.



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