Answers: It’s complicated. And, um, obviously.
After politely asking about his family, Letterman got into the dirt everyone really wants to know. Why did Chappelle, after signing a reported $50 million deal to continue his hugely successful Comedy Central “Chappelle Show” for a third and fourth season, suddenly jet to South Africa, disappearing out of nowhere and abruptly ending the series?
“Listen, here it is,” Chappelle told Letterman. “Technically, I never quit. I am seven years late for work.”
Lots of laughter from the audience. “Boy, are you going to be in trouble when you go back,” Letterman said.
Chappelle tried to avoid the topic by going on a rant: “You know, it’s like getting divorced in the ’50s. People didn’t go to divorce court. They looked at their wife like, ‘Baby, I’m going to get a pack of cigarettes. I’ll be right back.’ And they just leave with the clothes on their back and make a go of it. There wasn’t even internet back then. You could move 11 miles away and have a whole new life.”
Letterman wasn’t going to let Chappelle off the hook, reminding him that at the time, there was wild speculation about what happened: “You lived in South Africa for an extended period of time.”
“Well, no, I was there for two weeks,” Chappelle pointed out. It’s true: He was spotted in multiple places across the country in the weeks afterward. “There’s not too many good hiding places left in America.”
“But there were — am I right about this — there was great mystery about this strategy on your part, was there not?” Letterman pressed.
Chappelle went on about how he wouldn’t know whether it was mysterious, because he left the continent, so he didn’t hear any of the fallout. Letterman tried another angle, reminding Chappelle of all the money he walked away from: “Do you regret saying, ‘I don’t want this enormous sum of money?'”
Finally, Chappelle got real, with an extended analogy:
Okay, look, Dave. It’s very hard to go through something like this because no one’s really done it before. So there’s not too many people that *don’t* think I’m crazy, right? So I look at it like this. I’m at a restaurant with my wife. It’s a nice restaurant, we’re eating dinner. I look across the room and say, “See this guy over here across the room? He has $100 million, and we’re eating the same entree.” Okay, fine, I don’t have $50 million or whatever it was. But say I have $10 million in the bank. The difference in lifestyle is minuscule. The only difference between having $10 million and $50 million is an astounding $40 million. Of course…of course, I would have liked to have that money.
Much laughter from the crowd. “You’re right,” Letterman said. “It is — it’s $40 million is the difference.”
Chappelle was now all ramped up. “You know, because when you quit, like my friends will try to make me feel better, but no one has been through that, so they’ll say…’You know, Dave, at the end of the day, you still have some integrity.’ That’s great. I’ll go home and make the kids some integrity sandwiches!”
“There’s nothing anyone can say,” Chappelle concluded. “You do what you feel like you need to do at any given time.”
“There’s the answer,” Letterman said, finally. “And how do you feel about what you felt you needed to do?”
Chappelle sighed. “That’s a very complicated answer. Because I felt a variety of ways in the last 10 years,” he said. “You know, whenever there’s something that I’d like to have that I could have afforded that I can’t now afford, well, then I’m upset about it. But then when I see a guy going to do a job that’s time consuming and he doesn’t have the free time to do things that I get to do, then I feel good about it.”
“But, overall, in your heart, in everyone’s heart, we know money is not the answer or the solution,” Letterman pointed out. “And let’s just say you had the $40 million, who is to say you would be a happier or better person?”
“I think I might be a happier person,” Chappelle shot back. “I don’t know. There’s no way of knowing. But you know, sometimes I listen to a Jay Z record and it starts to make 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 11 years.”
“But who among us doesn’t make choices we have regrets about?” Letterman philosophized.
“All of us do,” Chappelle said.