Uptown Saturday Night (1974)

Sidney Poitier and Bill Cosby team up in this hilarious misadventure as buddies Steve and Wardell, who head uptown to a swanky nightclub. Unfortunately, thieves hit the club and steal Steve’s wallet — which happens to hold a winning lottery ticket. Poitier also directed this classic 1970s comedy, which co-stars Harry Belafonte as Godfather figure Geechie Dan Beauford and Richard Pryor.