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Mr. Oscar Night himself (well, when there isn't a must-see Laker game), Jack Nicholson is one of two gents to have received three Oscars to date. Two of them were for lead actor and one for supporting. He has 12 nominations to date, and while he probably should have received one or two more over that stretch for this and that, he'll likely pick up another before it's all said and done. Fun fact: two of Nicholson's Oscars came for performances in James L. Brooks films.
"One Flew Over the Cuckoo's Nest" (1975) - Best Actor
"Terms of Endearment" (1983) - Best Supporting Actor
"As Good As It Gets" (1997) - Best Actor