Losin' It (1983) on Netflix

On a Friday morning in the early 1960s, Southern California high school seniors Dave Cartman (Jackie Earl Haley), Spider Church (John Stockwell), and Woody (Tom Cruise) prepare for their school day, to be followed by a long-awaited trip to Tijuana, Mexico. Upon arriving at school, Perlman (Ricky Powell), the fourth member of the expedition, suddenly withdraws and leaves his friends $95 short of their required funds. Dave's entrepreneurial younger brother, Wendell (John P. Navin Jr.), nicknamed Wimp, offers to supply the money, but only if he is allowed to go in Perlman's place. Dave reluctantly agrees to the proposal, hoping Wendell will not interfere as the older boys tour the city's nightclubs and brothels. The group faces another obstacle when Spider is given an after-school detention for defending himself against an irate football player. However, Spider is undeterred and escapes the campus to joins his friends.