By Jackson McHenry
Updated June 11, 2014 at 01:42 PM EDT
Dave Chappelle
Credit: Rick Kern/WireImage

Have you ever wondered what would happen if you just decided to stop showing up to work? Dave Chappelle has. And in 2005, he did — walking away from his hit Comedy Central series Chappelle’s Show midway through its third season.

The reclusive comedian explained his reasoning in an interview with David Letterman on Late Night Tuesday. “Technically, I never quit. I’m seven years late for work,” he joked. Work briefly continued in his absence, however, as the network aired three episodes from the show’s incomplete third season in 2006 before calling it quits.

In the interview, Letterman brought up the issue of compensation: Comedy Central promised Chappelle an “enormous sum of money” to continue shooting his show after the third season. Chappelle agreed to the money — before jumping ship. But Chappelle was cagey about his reasons, commenting only that “there’s not too many people that don’t think I’m crazy.”

Chappelle compared the experience to eating in a fancy restaurant where the guy across the room from you has 100 or 50 million dollars and you only have 10 million, but you’re both eating the same entree. “The difference in lifestyle is minuscule. The only difference between having 10 million dollars and 50 million dollars — is an astounding 40 million dollars.” (The deal Chappelle signed in 2005 was reportedly $50 million).

So Chappelle walked away from the money, and Chappelle‘s Show ended. Ponder the concepts of regret, money, and time-as-imposed-by-the-comedic-industrial-complex in the clip above. And if you’re in the mood for more zen koans (as well as humor about race, class, and everything else), Chappelle has also announced a series of live shows at Radio City Music Hall on June 18th to 26th.

Late Show With David Letterman

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