Chillopedia: After playing various roles for over three decades on the silver screen, Jack Nicholson is one of the most versatile actors of all time. Nominated for the prestigious Oscar Awards a record 12 times, he has won three of them as well. He won it twice for best actor playing a leading role and once as best actor in a supporting role. No other male actor in the history of the Oscar Awards has ever been nominated 12 times or has won it thrice. He exudes a very strong personality in whatever role he plays.