Jerry Maguire (1996)
In his second Oscar-nominated role (Born on the Fourth of July earned him his first), Cruise played Jerry, a sports agent who has a moral epiphany and is fired for expressing it.
The best moments in the film are where he bonds with his love interest's (Renee Zellweger) son, Ray (Jonathan Lipnicki).
Also read: Gals who looked great in black