Just saw the request to put them in order. If forced to, I'd say:

1) Rocky - when I was young played a role in helping me believe was possible if you believe and work hard.
2) Brian's Song - first movie that ever made me cry.
3) Field of Dreams - love the mix of the supernatural into the story line.
4) Jerry Macguire - loved his commitment to his beliefs and convictions.
5) Raging Bull - being Italian-American, I can't help but like De Niro and Pesci.

-Chris