Dave Chappelle becomes first comedian to headline Summerfest’s biggest stage

The Milwaukee festival announced Monday morning that Chappelle will headline the American Family Insurance Amphitheater on Sept. 11. There has never been a standup-comedy headlining show at the venue in the amphitheater’s 34-year history.

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Comedian Dave Chappelle is photographed in 2020 in North Charleston, South Carolina.

Comedian Dave Chappelle is photographed in 2020 in North Charleston, South Carolina.

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Comedian Dave Chappelle will be the first comedian to headline Summerfest’s biggest stage in its history.

The Milwaukee festival announced Monday morning that Chappelle will headline the American Family Insurance Amphitheater on Sept. 11. Tickets go on sale at noon June 11 at the Summerfest ticket office, 200 N. Harbor Drive, and ticketmaster.com. Ticket-price information wasn’t immediately available, but tickets will include Summerfest general admission on Sept. 11.

The American Family Insurance Amphitheater, which underwent a $51.3 million renovation last year, opened as the Marcus Amphitheater in 1987. There has never been a standup-comedy headlining show at the venue in the amphitheater’s 34-year history.

But comedy was long a part of Summerfest’s identity, even though it’s been a rarity at the festival in recent years. 

Bob Hope was one of the festival’s first big headliners, performing two nights at County Stadium in 1969, before the festival relocated to what is now Maier Festival Park the following year. And of course George Carlin’s arrest in 1972 for performing his “Seven Words You Can’t Say on Television” bit is one of the festival’s most famous moments. 

Jay Leno, Billy Crystal, Jon Stewart and Tracy Morgan are among the comedians who played the festival in subsequent decades. And while Summerfest officials billed Chappelle’s show Sept. 11 as his festival debut, he actually played the festival in 1999. 

In 2006, comedian Lewis Black said at his Summerfest show that he would headline the Marcus Amphitheater the following year, but that never happened. There was no standup comedy at the festival at all from 2007 to 2012. Black headlined the BMO Harris Pavilion in 2013, but there has not been a standup show at Summerfest since.

In announcing the Chappelle show, Summerfest pointed out it was for “one night only.” That’s generally not how Chappelle works, especially in Milwaukee. He performed a sold-out, four-night residency at the Pabst Theater in March 2020, just before the COVID-19 pandemic shut down everything. And he had an eight-show residency at the Pabst in 2016; all those shows sold out quickly, too. 

Festival officials also stressed that no phones, cameras or recording devices will be allowed at Chappelle’s show, with all smartphones and smart watches locked in Yondr pouches upon entry for the duration of the show. Anyone caught with a phone in the venue will be ejected. That’s been standard practice for Chappelle’s past performances as well. 

Monday’s announcement leaves Summerfest with one amphitheater headliner slot to fill at the 2021 festival, for Sept. 4.

The other amphitheater shows include: 

  • Green Day, Weezer and Fall Out Boy (Sept. 1)
  • Luke Bryan with Dylan Scott (Sept. 2)
  • Chance The Rapper with 24KGoldn, Teezo Touchdown and DJ Oreo (Sept. 3)
  • The Jonas Brothers with Kelsea Ballerini and Spencer Sutherland (Sept. 8)
  • Chris Stapleton with Sheryl Crow (Sept. 9)
  • Zac Brown Band with Gabby Barrett (Sept. 10)
  • Dave Matthews Band (Sept. 15)
  • Megan Thee Stallion with Polo G (Sept. 16)
  • Miley Cyrus with The Kid Laroi (Sept. 17)
  • Guns N’ Roses (Sept. 18)

Tickets are on sale for all of those shows at the box office and through Ticketmaster and include Summerfest general admission.

Last month, Summerfest officials also unveiled the headliner lineup for the grounds stages, featuring about 100 acts, including Run The Jewels, Diplo, Wilco and Sheila E. General admission tickets are also on sale at the box office and on Summerfest’s website.

This will be the first Summerfest since 2019. The festival was forced to cancel for the first time in its 53-year history last year because of COVID-19. 

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