You can not imagine how hard this list was to compile. Rather, how hard it was to narrow this list down to 3 films. Near impossible I tell you! But here is what I came up with:
Better Off Dead (1985)
In this film, his first with director Savage Steve Holland, he plays Lane Meyer. This is actually the first movie I saw with him so it's probably why it got chosen to be in thist list, not to disparage the film any because it is a great film. So many cool "sub-plots" too: the persistent paperboy, the strange psuedo-junkie best friend, the car racing exchange students....
Say Anything (1989)
It would be absolutely impossible to have a best of John Cusack list without this film in it. Cusack plays the lead character Lloyd Dobbler in this Seattle-based post-high school graduate film.
High Fidelity (2000)
I'm not sure how it would be possible to not have a John Cusack list with this one either. Especially considering this film by itself is one of my favorites. In it, he plays Chicago record store owner Rob Gordon. This film was based on a Nick Horby novel, which was also a great book but based in London, not Chicago.
Seriously, the film list of this actor is amazing, he has done so many great films....
Sixteen Candles, Class, The Sure Thing, Better Off Dead, One Crazy Summer, 8 Men Out, Say Anything, True Colors, City Hall, Grosse Pointe Blank, Con Air, Thin Red Line, Pushing Tin, High Fidelity, America's Sweethearts, Serendipity, Identity, Runaway Jury, Must Love Dogs, War Inc.......
See why it was so hard?