This week, Dave Chappelle steps back into the spotlight for real as he finds himself preparing for a five-night one man show at Radio City Music Hall in New York later this month. Thus, he’s on press duty and one of those stops happens to be David Letterman’s couch, a spot he hasn’t been on in ten years.

Dave & Dave talk about a few things, namely him leaving Chappelle’s Show and walking away from that enormous sum of money. Once the awkwardness gets out of the way, Chappelle talks about money in a social correctness that is as Chappelle as it gets and more. Here’s five main takeaways from the interview.

1. Comedy Central Airing Season 3 Effectively Ended Chappelle’s Show
Here’s the main point of why Dave won’t come back to Comedy Central because even though he walked away from the deal (“I’m seven years late for work”), Comedy Central went against his wishes and aired the “lost episodes” anyway. That third season is largely forgettable because of this and we’re not even talking the “Pixies” sketch that kicked all of this off.

2. He Didn’t Live In South Africa … Technically
He left and went to Africa for two weeks. In his words, “There’s not too many places you can hide in anymore.”

3. $50 Million Is Better Than $10 Million
He may eat the same amount of food as a man richer than him but that $40 million difference sure makes things interesting.

4. He Doesn’t Completely Regret Leaving The Show
Even by bypassing all of that money, Dave can still say leaving his child and the funniest show on television while it was hot is “complicated”. “Money is the fuel for choices.”

5. Jay Z Rapping About Money > Dave Chappelle Without $40 Million
Money, to Chappelle would make him happy but it wouldn’t necessarily define him as he’s gotten a few riches that money can’t buy. But, he feels the same way we all feel when we hear a Jay Z song these days, belittled and hurt because that man literally tells us what he did this week in terms of balling.