Almost a decade ago Dave Chappelle walked away from his mega-hit sketch comedy series Chappelle’s Show. At the time the program was one of the most talked about shows on television, and it helped put Chappelle in the conversation for “funniest man alive.” But then it abruptly ended.

The comedic legend sat down with David Letterman last night (6/10) to discuss not returning for a complete third season to the popular show he created.

“Technically, I never quit. I’m seven years late for work,” joked Chappelle.
Chappelle also addressed giving up the reported $50 million contract from Comedy Central to continue Chappelle’s Show and whether he regrets not taking the money.

“I look at like this; I’m at a restaurant with my wife. Its a nice restaurant and we’re eating dinner. I look across the room and say, ‘You see this guy across the room. He has $100 million dollars, and we’re eating the same entrée,” said Chappelle. “Ok, fine, I don’t have $50 million dollars. Let’s say I have $10 million in the bank. The difference in lifestyle is miniscule. The only difference between having $10 million dollars and $50 million dollars is an astounding $40 million dollars… Of course I would like to have that money.”

When Letterman suggested having that $40 million may not necessarily make Chappelle a happier person, the comedian quipped, “I think I might be a happier person… Sometimes I listen to a Jay Z record and it starts making me feel bad about some of the choices I’ve made. This guy’s had more fun on two songs than I’ve had in the last eleven years.”

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