Dave Chappelle Stand-Up on Maui

"The theme of the night is...hopelessness.  Now you can't have hope without hopelessness." - Dave Chappelle

Maui finally got to host Dave Chappelle and his stand-up comedy, a visit that was waayyy long overdue.  After practicing stand-up around New York's comedy circuit, a few failed TV pilots, and several silver-screen appearances, Chappelle really gained notoriety when he burst onto the entertainment scene 10+ years ago with Comedy Central's "Chappelle's Show" in 2003.  Known internationally for his character comedy and jokes on racism, sexuality, and pop-culture, Chappelle ranks #43 on Comedy Central's "100 Greatest Stand-Ups of All Time."

Tickets for Dave Chappelle's stand-up show, scheduled for February 5th at the Maui Arts & Cultural Center (MACC), went on sale January 15th.  No less than 24 hours later, a second show was arranged for those who missed out on tickets for the first show.  Chappelle's comedy was in such high demand, MACC was forced to add three more shows, giving Chappelle a total of five sold-out shows in the MACC's 1200-seat Castle Theatre.


Luckily I was able to snag two tickets for his final show, February 11th at 10:00 pm, as a Valentine's gift for my husband who considers Dave Chappelle to be one of his "favorite comedians of all time."

Oʻahu comedian James Mane opened, warming up the crowd with jokes about living life as a "fat boy" with his 6' 7" stature and weight of 180+ lbs., emphasizing on the "big plus."  He finished off with a round of observational comedy about his Samoan family, yet still making it relateable by ending with a punchline that would "ruin baby-sniffing for everyone."

DJ Trauma hyped up the crowd, hitting the turntables for "everyone who went to high school in the 80's, 90's, and 2000's," and had everyone dancing out of their seats.

Finally, Dave Chappelle was welcomed on stage to a standing ovation. He started off with jokes about Maui, telling the crowd about whale watching being "the whitest sh*t I have ever done" and the island is so beautiful "even racism is nice here."

To quote the man himself, "The theme of the night is...hopelessness.  Now you can't have hope without hopelessness."  Many of the jokes were bad.  Bad because they involved stories of guilt: yelling at a homeless man on the street; the resurfacing of an old sex tape; children repeating inappropriate and then having to explain their meaning; and sneaking out late to get away from the family.  Personal experiences that are regrettably relatable.


My husband & I with our tickets before the show.   /  DJ Trauma "dual crowd selfies" with Dave Chappelle.