After several years of small roles and experimental screenwriting during his early career, Jack Nicholson got his big break in 1969 with Easy Rider. The next year Five Easy Pieces made him a star. Since then the 12-time Academy Award nominee has won Best Actor twice (One Flew Over the Cuckoo's Nest and As Good as It Gets). This critical study examines each of Nicholson's film roles, as well as his screenwriting and directorial efforts. Fascinating personal insights are provided through interviews with stars such as Mews Small, James Hong, Millie Perkins, Michael Margotta, Shirley Knight, Joe Turkel, Ed Nelson, Hazel Court, the Monkees, several Apollo astronauts, Hell's Angel Sonny Barger, Peter Fonda, Bruce Dern, and many more.