Dogfight

Dogfight is a movie starring River Phoenix, Lili Taylor, and Richard Panebianco. Before leaving to fight in Vietnam, a group of teenagers play a game where they try to seduce the ugliest girl they can find.
In the fall of 1963, Eddie Birdlace is an 18-year-old Marine Corps volunteer who is about to ship out with three of his buddies for a tour of duty in Vietnam. Planning a massive blowout for their last night in San Francisco, Eddie, his buddies, and a number of other Marines set up a contest they call a "dogfight."