Happy 50th Damon!
The Last Boy Scout (1991)
This film was directed by Tony Scott (Top Gun, Beverly Hills Cop, True Romance, etc.), produced by Joel Silver (Predator, Die Hard, Conspiracy Theory, etc.) and also stars Bruce Willis.
Wayans plays Jimmy Dix, a former professional quarterback for the fictitious football team, the Los Angeles Stallions.
Celtic Pride (1996)
In this film starred Daniel Stern and Dan Akroyd as avid Boston Celtics fans, Damon stars as the star player for the Utah Jazz, who are playing the Celtics in the NBA Finals.
The Great White Hype (1996)
In another sports comedy, Damon plays James "The Grim Reaper" Roper, the reigning heavyweight boxing champion in the movie whose unscrupulous promoter, played by Samuel L Jackson, pits him in his next fight against an amateur white man, played by Peter Berg.
This film also starred Jeff Goldblum, Corbin Bernsen, Jon Lovitz, Cheech Marin, John Rhys-Davies and Jamie Foxx.