And just for the record - Ruth Two Bears should have won.
This I will say. Lili Taylor is not the most attractive woman in the world, but she's an actress who has done well for herself despite being, at best, quirky-looking. I really think she's plain, which is different from ugly. However, she appears in roles where she's supposed to be human-looking. In most movies and TV shows, the plain person only has to do something with her hair and probably take off her glasses in order to be beautiful, and she only needs the right clothes to show off the beautiful body she certainly has. And while I don't think Lili Taylor becomes beautiful over the course of the movie, it becomes apparent that she isn't ugly, either. She becomes more comfortable with herself, and that makes her look better. She relaxes, and she is no longer concerned with how she'll appear to other people. This may in part be because she's already been hurt as much that night as she can be, so it's all uphill from there.
She plays Rose. River Phoenix plays Eddie Birdlace, a young Marine on his way to Okinawa. During a stop in San Francisco, he and various of his Marine buddies have what they call a "dogfight." Each man pays an entry fee, with which they rent a bar and buy plenty of food and drink. The remainder of the money goes as prizes. For the man who brings the ugliest girl. Eddie picks up Rose in her mother's diner and takes her, but when she gets off work, he realizes that she's not actually ugly and certainly not ugly enough to win. Not only that, but as they talk, he gets to actually like her. He tries to keep her from going, but any real admission would be to tell her what's going on. Only while she's there, she learns the truth from Marcie (Elizabeth Daily), a prostitute one of the men has hired to win the game against the rules. Rose reacts about the way you'd expect, which actually makes Eddie feel guilty. He ends up taking her on a real date, seeing all that can be seen in San Francisco in the middle of the night.
I do find it interesting that Eddie's personality is based in part on who he's with. As he spends more and more time with Rose, he softens. He stops being such a Guy. Phoenix was twenty-one at the time, and I think Eddie was even younger. He got his father to sign the paperwork so that he could join the Marines at sixteen. Though if, as he says, Eleanor Roosevelt was actually dead when he enlisted, he can be no older than a few days short of eighteen. Lili Taylor was a few years older than River Phoenix, and I think Rose probably was, too. She is practical, in no small part because she's never been able to be anything else. She's a bit wistful, too, because she wished she could have been. And when she spends time with Eddie, he starts to become a better person. But when he gets back with his Marine buddies, he goes back to having to impress them. He's young enough so that he almost certainly doesn't know who he is yet, and that may be why he agreed to be a part of such a cruel game in the first place.
The funny thing is that one of the guys gives up a chance to spend time with an attractive woman who seems genuinely interested in him so that he can pick up an ugly girl to mistreat. He has to show up the guys. I mean, he probably also wants to win the money, but the winnings aren't a heck of a lot over what he had to put in the pot to begin with. I'm certain he didn't think of it as being cruel. This is in part because I'm certain that he didn't think of the girl's feelings at all. This is not to say that I think he's a sociopath. I doubt most of the men involved in the "game" are. On the other hand, I didn't find it the slightest bit difficult to believe that guys would do this. I mean, for one thing, military training isn't exactly designed to heighten empathy. And, let's face it, young people aren't exactly the most in tune to people's feelings going in. The guys were just being young, selfish guys. Or, you know, young guys.
The challenge, then, was making River Phoenix both believable in his treatment of her and believable when he comes to regret it. This means it's another one of those roles almost custom-designed to make you regret someone's death. A little over two years after the movie's (extremely limited) release, River Phoenix died on a sidewalk in Los Angeles. Playing Rose basically took being plain and kind, which is not challenging. Though most actresses would have trouble truly managing the "plain" part. But with Eddie, he had to start young and dumb--young and [i]cruel[/i]--and from then go on to earn Rose's trust. And ours. We must believe that he now realizes he hurt her and doesn't mean to do it again. We must also, of course, know that there is still the risk of it. After all, at the end of the night, Eddie goes back to his friends, none of whom show the slightest remorse at their activities. His now being a good person who would shun his best friends wouldn't ring true, and even River Phoenix's talents couldn't overcome that.