Dave Chappelle shocked fans — and the showbiz world — when he walked away from a reported $50 million contract at Comedy Central 10 years ago.
With his cultural impact already set, the thousands of frat bros yelling “I’m Rick James, bitch!” — from one of his popular sketches — may have contributed to his decision to walk away from the fame his hit “Chappelle’s Show” brought on.
He dropped off the radar and left few clues of what he’s been up to since.
Last week, he finally talked about what it was like to walk away from all that money during an appearance on David Letterman’s show.
And now, after a few small-town performances last year, Chappelle makes his long-awaited return to the big stage with nine shows at Radio City Music Hall, starting Wednesday. His musical guests include Erykah Badu, the Roots and Nas.
To mark his return, take a look at eight memorable and insightful moments of Chappelle’s career.
‘Block Party’
Before he walked away from public life, Chappelle collaborated with director Michel Gondry on this 2005 concert film about throwing a block party in Clinton Hill, Brooklyn. Acts included a pre-Kimye Kanye West, Lauryn Hill, Mos Def and the Roots, continuing his love of blending music with comedy.
When he befriended impostors
Last week, Chappelle stopped by “The Tonight Show” to talk to Jimmy Fallon about impostors on social media. Turns out, Chappelle likes stalking them more than he likes actually tweeting.
‘Half Baked’
If you didn’t watch this 1998 movie at least once a weekend, you probably didn’t go to college in the early 2000s. The dorm-room staple immediately entered the pantheon of best stoner movies of all time, and helped launch Chappelle into fame.
‘Robin Hood: Men in Tights’
Before he was “Rick James, bitch,” Chappelle was Ahchoo in this 1993 Mel Brooks film. In this clip, he sends up a famous Malcolm X speech, saying: “We didn’t land on Sherwood Forest, Sherwood Forest landed on us!”
The Prince sketch
This 2004 follow-up to the Rick James sketch found Charlie Murphy and friends playing basketball at Prince’s house. Absurdities of the bit included Prince (played by Chappelle) serving pancakes to celebrate victory.
That time Prince had a sense of humor about it
In 2012, “Chappelle’s Show” co-creator Neal Brennan told Grantland’s Bill Simmons this story from right after the Prince sketch ran. It’s an absurd tale of being invited to a party with Prince, where the mercurial singer did in fact offer them pancakes, which would have made a good sketch on its own.
The Rick James sketch
The now-legendary 2004 bit that cemented “Chappelle’s Show” in the comedy history books also probably helped lead to its demise. Chappelle could only take so many white dudes yelling “I’m Rick James, bitch!” before it got to be too much.
‘Killin’ Them Softly’
Chappelle’s HBO special from 2000 was his big breakout moment, and the stand-up hour became an instant hit on college campuses thanks to the burgeoning new digital-file-sharing era of the early 2000s. It’s considered one of the best comedy specials of all time, thanks to memorable lines like “sprinkle some crack on him.”