Rounders

LetterboxD review link

This is a guilty pleasure favorite for me. It’s not an art-house film. It treats women like crap. There might literally be 0 non-white people in it. It has a cheesy soundtrack that swells my emotions. It was one of the first films that endeared me to Ed Norton. But more than anything else, this is a guilty pleasure because it pushes Matt Damon’s career further along the path of lone-wolf, self-made-man, Horatio Alger type stories. And despite the fact that I fundamentally don’t believe in a world like that, that objectivists make me laugh and shake my head, I can’t help but get swept up.

For Matt Damon Goodwill Hunting, the Bourne series, Rounders and even his turns in the Oceans’ N films are a big part of his Hollywood success. In each, he plays a man succeeding largely on the parts of his own hard work, wits and charm. It’s much easier to tell a story about a guy like that, to get the film watcher to buy in and see himself on screen than to tell much more complicated stories about social forces, or about doubting yourself even if you have tons of talent. This is not a new argument, but I find it fascinating every time I sit down and watch Good Will Hunting or Rounders - because despite my better self, I can’t help but get caught up.