Dave Chappelle

In the early to mid-2000s, Dave Chappelle was enjoying huge success with his Chappelle’s Show on Comedy Central. It was such a hit that he got a $55 million contract to continue the show and retain a cut of DVD sales. However, at the peak of its success, he aburptly walked away … and left the spotlight, sparking a media frenzy about where he was.

Nearly a decade later, Chappelle talks about leaving the show in a rare talk show appearance on The Late Show with David Letterman.

“Technically, I never quit. I’m seven years late for work,” he said, as the crowd broke into laughter.

As the interview continued, Chapelle talks about leaving for South Africa, his regrets about walking away from $50 million, and more.