You're talking about the labels or venue's instead of talking about the comedians. Chappelle didn't get that gig because he was made of money. He got it because all of his stand up shows leading up to that were liked and he got their attention. That's how becoming a famous comedian works. You're popular enough to get someone to notice you. It's how most bands work, too. Motley Cru started off as nobody's before getting noticed from a small venue where they were getting popular.