Very difficult to choose between High Fidelity and The Grifters. Both two of my favorite movies ever.
Max! It's a good movie and very underrated.. john cusack + hitler = 2 hours of historic entertainment.
I voted for Grosse Pointe Blank 'cuz One Crazy Summer wasn't on the list. it's awesome seeing him and his sister in GPB and I love when other alumni at his reunion ask him what he does for a living and he casually tells them "I'm a professional hitman..." and Being John Malkovich would round out my top three. ....aaaaand Better Off Dead (he's skiing on one ski!)
Better Off Dead would be number 1 for me. The Sure Thing would be number 2 or close to number 1 depending on my mood that day. I also like Hot Pursuit a lot. High Fidelity was great, and Grosse Pointe Blank was pretty good too. I can't forget to add Being John Malkovich was good, but the movie as a whole overshadows John Cusack which isn't necessarily a bad thing, just hard to think of him first when I reflect on that movie.
A good Cusack movie not mentioned yet is Eight Men Out. Hardly my favorite Cusack film, it still is a pretty good movie.