In Caddyshack (1980), Chevy Chase's character (Ty Webb) is laid back, good at golf, and apparently extremely rich. At one point in the film, when he and Lacy are at his house, Lacy mentions that Ty has a bunch of uncashed checks for $70,000 each just laying around (and Ty even tells her to just keep one of them!).
Also, when Ty and Judge Smails make a bet, Ty has no problem betting $40,000 of his own money, so clearly he does have exorbitant amounts of cash that he can spend so freely.
Lastly, AFAIK, I don't think he works at all - just plays golf every day - so it's not like he has a high paying job which could easily explain this.
Why/how does he have so much money?
Follow-up question: Why were all of the checks for the same amount? Were they from a lawsuit/settlement of some kind, given that Lacy also mentions there being a court summons?