Dave Chappelle Delivers Memorable Performance at Milwaukee’s Summerfest on 9/11

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Photo via Summerfest

Dave Chappelle

Legendary comedian Dave Chappelle came to Summerfest on a rather unusual Saturday night. It was 9/11 and on what is usually a quiet and solemn day, Chappelle brought the light and laughter to the American Family Insurance Amphitheater.

The jokes were reminiscent of the jokes on Chappelle’s groundbreaking sketch comedy show that made him the famous and adored comedian he is today to many. The comedian and actor isn’t new to Milwaukee, which is the first thing he said when he entered the stage. Chappelle performed at Milwaukee’s Pabst Theater before the pandemic hit, which became an important topic amongst all of Chappelle’s jokes.

The pandemic and 9/11 made for a memorable and reflective night in Milwaukee. Chappelle sounded off on topics from Mike Pence to Dick Gregory to DMX. It was a classic Chappelle-style comedy show, which included tales from his meetings with celebrity friends and travels around the world. Chappelle even joked with audience members and his own bodyguards.

The show began with music spun from DJ Trauma, which included tributes to Biz Markie and DMX by playing the hits of each of the late musicians, “Just A Friend” and “Party Up (Up In Here),” and it got the crowd rightfully hyped and prepared. Before Chappelle took the stage, he brought a friend with him as his opening act, comedian and actor Donnell Rawlings, who played alongside Chappelle on “The Chappelle Show” Marshall Brandon also performed as an opening act.

Chappelle received a standing ovation when he entered the stage, dressed in a jumpsuit similar to the one in his Netflix comedy specials and smoking a pack of cigarettes. 

The comedian jumped right into it, and he didn’t fail to tell Milwaukee that he “loved and respected” them and how honored he was to perform at Summerfest. The comedian even congratulated the newly crowned NBA Champions, the Milwaukee Bucks.

At a random moment, Chappelle asked the audience if anybody was from Chicago. “You all came to this show tonight in Milwaukee to get away from all the murder in Chicago,” he said. Chappelle’s jokes ranged from racism and brutality to other political topics and music.

One audience member yelled, “Run for President, Dave.” At which point, Chappelle took a crack at his real-life departure to Africa after leaving his television show, “I would run for President, but I would probably quit and run off to Africa.” Another audience member asked the comedian, “Tell us about Dick Gregory,” and Chappelle granted the audience’s wish and went into a story about the time he met one of his idols and spoke to him in an unforgettable phone conversation.

Chappelle couldn’t leave without paying tribute to DMX, in which he revealed that the rapper visited his home two weeks before his death. The comedian showed his love for music when he revealed that one of his bodyguards, Brandon, could sing.

Chappelle joked that he liked to go to a shooting range when he hires bodyguards and his newest bodyguard likes to sing, which makes it a fun time in the Chappelle camp. The comedian motioned for the bodyguard to come on stage to sing a note, and the bodyguard showed the audience a snippet of his skills with a rendition of Boyz II Men’s “It’s So Hard To Say Goodbye To Yesterday.” The singing bit was met with cheers from the audience and roaring Chappelle fans.

At last, Chappelle recalled where he was on the fateful day of 9/11, and mentioned how it was vastly different from this night in Milwaukee. Chappelle reflected on the last 20 years, and how performing in front of a sold-out crowd in Milwaukee was “one of the greatest moments of his life.”

After a long wait outside to get into the biggest stage at Summerfest to see the biggest comedian on the planet, fans left —with Chappelle-designed face masks on their faces and sealed phones in hand—at the very least, happy and hopeful.