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Peter O'Toole vs. Gregory Peck (1962)
It's so unfair. Seriously? T.E. Lawrence up against Atticus Finch? We have to choose?? We probably couldn't still, but the Academy closed their eyes, took a deep breath and opted for Peck, a vet who hadn't won yet against an up-and-comer who would surely have his day. Or would he? Alas, O'Toole famously (or perhaps infamously) never did get his hands on one of those trophies, but his performance belongs to the ages.