(born 1937) Part bohemian beatnik and part establishment, three-time Academy Award winner Jack Nicholson (One Flew Over the Cuckoo’s Nest, 1975; Terms of Endearment, 1983; As Good as it Gets, 1997) has brilliantly painted the landscape of the American male of the 1960s, 1970s, 1980s and 1990s. His expressiveness and intelligence as an actor are undeniable. Nicholson first played lead at twenty but his break came in the counterculture cult flick Easy Rider (1969). He has since worked with directing legends such as Stanley Kubrick, Antonioni, Polanski and Milas Forman. Refusing to give in to Hollywood’s casting conventions, Nicholson picked roles as disparate as dapper detective, mental patient, pothead anti-hero and devil—once with a capital D. His smile is phenomenal: its dazzling transformation from affectionate to demonic in The Shining (1980) renders the movie a horror classic.