Brewster's Millions (1984)

Silly but fun Richard Pryor flick from the early 80s. The premise is about as contrived as it gets: washed-up baseball player Pryor discovers that he is the sole heir to a fortune from a distant relative. However, there's a catch: in order to instil good spending habits, the dying relative has placed a rather sadistic catch on the inheritance: Pryor must spend $30 million in 30 days, legitimately (i.e. he can't just give to charity). If he succeeds, he will then inherit $300 million; if he fails he gets nothing. Alternatively, he can take a "wimp out" clause and pocket $1 million. About the only the only other thing I need to add is that the accountant charged with ensuring that spends every penny is the love interest (played by Lorette McKee) who is not in on the "game" and despairs at watching Pryor spending like there's no tomorrow.