Dogfight (1991)

The rules of the dogfight were simple. Everyone puts in fifty bucks. The guy with the ugliest "date" wins.

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”.