Honestly I was going to like this before I even watched it because it's Dave Chappelle. But after watching it I liked it so much more because, contrived or not, it seems like he's being extremely honest. He's talking about regret and sticking with decisions and problems people have to face even if they don't have 50 million dollars dangling in front of them.
However, the part I liked the most was his thoughts on starting out. Talking about opening for Aretha Franklin at 19 but it not mattering because no one was there to see him. And he was free because he realized no one cared how he did other than himself. Pretty sure the same goes for everyone.