30 Oscar losers that should have been Oscar winners

Oscars statuettes (Photo by Matt Petit - Handout/A.M.P.A.S. via Getty Images)
Oscars statuettes (Photo by Matt Petit - Handout/A.M.P.A.S. via Getty Images) /
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William H. Macy losing to Cuba Gooding Jr. – Best Supporting Actor (1997)

The Winner

Cuba Gooding, Jr. as Rod Tidwell, AKA the “Show me the money” Guy, in Jerry Maguire. He’s a football player who is represented by the titular sports agent. He is the Oscar to Jerry’s Felix. Meaning he’s the one who has personality.

The Loser

William H. Macy in Fargo, a cult classic if there ever was one. Macy plays Jerry Lundegaard, a car salesman who gets into some money troubles. He hires a couple of bad guys to kidnap his wife in order to get some ransom money out of his wealthy father-in-law. The only problem is, the guys he hired? Yeah. They’re bad. Did I mention that?

Why It Was Wrong

Cuba Gooding, Jr. is very good in this role. He’s very funny and, truth be told, he and the precocious kid are the only things that keep Jerry Maguire from being a boring rom-com. But, even though he gave one of the best Oscar speeches of all time, I still have to give more credit to William H. Macy.

Gooding was funny in a pretty obvious way. But Macy was funny in a very subtle, sincere, and even kind of sad way. While Gooding was going crazy with the “Show me the money” scene, Macy had to figure out how to be comedic in a room full of blood.

Ultimately, while both roles were well-executed, Macy’s was the more complex. He had to carry the sincerity and reality of an everyday guy who ends up witnessing murders. He had to carry the fear of being caught, the fear of getting out of hand, the fear of losing his wife. He carried it all against the desperation of needing money. But he also had to be funny. He was amusing, pitiable, and despicable all at once. Gooding, while great, had a much more clear-cut character arc. So despite the hilarity of Gooding’s performance, Macy has my vote.