Dogfight (1991)

Synopsis
River Phoenix stars in this period drama about a young man, naive in some ways and worldly in others, who learns an important lesson about the nature of beauty. In the fall of 1963, Eddie Birdlace (River Phoenix) 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 Viet Nam. 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 "dog fight." Each man contributes $50 to the pot, and whoever can bring the ugliest date for their meeting that night at the bar wins the prize. Not having much luck finding a suitable contestant, Eddie finds a plain and slightly zaftig woman named Rose Feeney (Lili Taylor), who works in a coffeeshop and dreams of a career as a folk singer. Rose agrees to go out with Eddie, partly because she feels sorry for him, but as the evening wears on, Eddie finds himself growing fond of Rose and tries to worm his way out of taking her to the "party" he's told her so much about. When Rose learns the true nature of the contest, she is furious, not just for herself but for the other women who were cruelly and pointlessly humiliated; Eddie, severely chagrined, asks her out to dinner, hoping to somehow earn her forgiveness. Noted folk singer Holly Near appears as Rose's mother. ~ Mark Deming, All Movie Guide