Dave Chappelle & Friends at Madison Square Garden

Dave Chappelle Rang In His Birthday By Bringing Out Some Incredible People At Madison Square Garden

Dave Chappelle, who just announced stand-up tour dates, celebrated his 50th birthday by doing what he does best: stand-up. Over a star-studded four day residency at Madison Square Garden, the comedian welcomed celebrity friends from the worlds of music, comedy, film, and sports to help make the celebratory vibe linger. One notable thing about Chappelle is his loyalty, and though some of his guests had controversies and legal issues, they were first and foremost friends and inspirations to him throughout his life.

From Busta Rhymes to John Mayer, we thought we’d go through the famous faces that have shaped and stood by Chappelle well enough to get an invite to his milestone birthday. Chappelle has proven to be thoughtful and reflective in recent years, his own controversy aside. We thought some of his friends might provide context.

Matt Rife

The comedian first met Chappelle after finding out he wanted Rife to stop by to hang out at his shack in Ohio. Over the span of hours, the two bonded, and Rife was eventually invited to perform at Chappelle’s camp. He offered to support Chappelle during a writer’s boycott, and has remained friends with Chappelle since.

Aziz Ansari

The comedian started out as a fan and caught Chappelle’s famous San Francisco sets in the early aughts. Over time, the two have grown friendly, to the point where Ansari was a speaker at Chappelle’s Mark Twain Prize commencement. In his speech, Ansari discusses how Chappelle broke the honorarium news to him, suggesting the two do mushrooms to celebrate.

Pete Davidson

Allegedly starting with post-Ariana Grande messages on social media and an invite to recuperate at Chappelle’s Ohio cabin, the two comedians have been friendly for a while. Chappelle clearly has a great deal of affection for Davidson, as seen in this SNL sketch where Chappelle ad-libs a request to look at Pete Davidson’s lips, causing him to break.

Chris Rock

Chris Rock has said it’s important to him that he and Chappelle get along, and the two comedy greats have become close over the last few years, doing everything from touring together to doing sets at Chappelle’s covid lockdown camp. Rock was incredibly supportive of Chappelle when he released his first new stand-up material in 2017, and has likened their friendship and ability to tag one another’s jokes without getting jealous to Jay-Z and Kanye’s relationship at the height of their powers.

Jon Stewart

When Stewart was coming into power as a comedian in the 90s, he was around Chappelle as he was starting to make his way in New York comedy. He said at Chappelle’s Mark Twain Award ceremony that Chappelle sought out people and positive experiences “so that he could then channel that through his art, and redirect that back to you as something completely different and new.”

Michael Che

Showing up to perform at Chappelle’s covid cornfield shows, the two have a fun and meaningful friendship, as evidenced by Che’s speech at his Mark Twain Prize event, saying “there’s one thing [about comedy] you’ll never know, and that’s what it’s like doing comedy while having a Dave Chappelle to look up to.” Also of note is the fact that Chappelle can hijack a promo interview for That Damn Michael Che with no love lost.

Ronny Chieng

The Daily Show correspondent and killer stand-up opened for Chappelle in 2014 in Brisbane, and in 2019 in New York. Chieng also took part in “Camp David” during covid, and has had nothing but love for Chappelle.

Michelle Wolf

Mutual admiration is a big part of Wolf’s friendship with Chappelle, who praised her White House Correspondents Dinner appearance. Wolf has opened for Chappelle, and even lived at his guest cottage during the days of Chappelle’s quarantine lockdown shows, writing on Instagram  to promote Chappelle’s 8:26 that Chappelle was “the most compassionate, thoughtful and brilliant person I’ve ever met. Of course he’s hilarious too but that doesn’t begin to encapsulate all he is. He built a stage so that we could all do what we love.”


The “Original Bad Girl of Comedy” took part in Chappelle’s covid shows, and is set to premiere a stand-up special produced by Chappelle, which has been a hobby of his as of late.

Donnell Rawlings

Whether doing stand-up or performing on Chappelle Show for $500 a sketch, Rawlings and Chappelle have been through a lot together. Chappelle has brought Rawlings on when he hosts SNL, and is producing his Netflix stand-up special.


Chappelle produced Earthquake’s recent Netflix special as part of his “Home Team” series. When Chappelle was attacked on stage, Earthquake spoke out, mentioning "Dave handled it like a pro. He is one of the greatest human beings I've ever met in my life."

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