Ruggles of Red Gap is one probably no one has heard of. It's a movie from the 1930s people either don't know or have forgotten, but damn I thought it was charming. Ed Norton had it as #3 on his fave movies list for RottenTomatoes.
Chasing Amy might be too chick flicky for you, idk. It's a critically acclaimed Kevin Smith dramedy from the mid-90s before he did Dogma.
Crash I have up there for reasons I mentioned. It's basically about how a series of events in L.A. revolving around race become connected to each other. It can be uncomfortable to watch and some people who've seen it think the movie itself can be racist. I don't necessarily agree as I think it depicts ugliness without condoning it at all, but you can decide if you watch it.
Cinderella Man is unequivocally my favorite movie. Always wanted to be a family man and so the struggle of boxer JJ Braddock to fend for his family during the Depression gets me in the drama hole. And Ron Howard is a great director, since Rush was a favorite of mine from 2013. Guy knows how to play up the character relations and real life tensions in a sports movie and make sports I would never usually watch very entertaining and visually interesting.
