The role: Sports agent Jerry Maguire

Nominated for: Academy Award (Best Actor), Screen Actors Guild Award (Best Actor)

Won: Blockbuster Entertainment Award (Favorite Actor - Comedy/Romance), Golden Globe (Best Actor - Comedy/Musical), MTV Movie Awards (Best Male Performance), National Board of Review Award (Best Actor), Satellite Award (Best Actor - Comedy or Musical)

Thoughts: Cruise was riding probably his highest wave in 1996, a successful franchise starter in the summer, a bona fide box office star having already appeared in three Best Picture nominees, etc. The awards season brought Cameron Crowe's "Jerry Maguire," the perfect vehicle for Cruise at the time, showing off the actor's dramedy range and landing him his second Oscar nomination.