Won for: Pvt. Trip, Glory (1989)
Should have won for: Take your pick. Arguably, Washington's Oscar for Glory was well deserved, but during his heyday from the late '80s to mid-90's, he gave a series of Oscar-caliber performances in hard-hitting dramas like A Soldier’s Story (1984), Philadelphia (1993), and Cry Freedom (1987), for which he also received a nomination.
Cuba Gooding, Jr.
Won for: Rod Tidwell, Jerry Maguire (1996)
Beyond 1991's Boyz n the Hood, which earned director John Singleton nominations for both Best Director and Best Original Screenplay, Jerry Maguire is about as good as it gets for Cuba Gooding, Jr.
Won for: Eddie "Scrap-Iron" Dupris, Million Dollar Baby (2004)
Should have won for: Joe Clark, Lean on Me (1989)
When Freeman spoke with THR a few years ago, he cited no-nonsense principal Joe Clark as one of a handful of roles that defined his five decade-long career. He was instead nominated for an Oscar in 1989 for his supporting role in Driving Miss Daisy.
Regarding his win for Million Dollar Baby he said, "It actually kinda felt anticlimactic. I guess you just sort of know you can only get so many nominations before they decide, 'Oh, why don't we just give it to him?'"