James Woods

Whether playing a hero or a villain, Woods is a master at making sleaziness seem sexy, and vice versa. Armed with a skinny frame, craggy features and explosive energy, this charismatic player dropped out of MIT to pursue acting. Although he spent the '70s languishing in small roles, he broke through as a psychotic criminal in the harrowing 1979 drama The Onion Field. It was a testament to his talent that he got typecast as a big-screen baddy: a manipulative drug dealer in Against All Odds, an S-and-M-obsessed cable TV operator in Videodrome and a Jewish gangster in Once Upon a Time in America. He earned his first Oscar nod for Salvador, as a reckless American journalist caught up in the title country's civil unrest. Yet despite his critical accolades, Hollywood didn't view Woods as leading-man material in films, perhaps due to his unconventional looks and manic energy. So while he spent the next two decades turning in excellent supporting performances on the big screen — a hustler in Diggstown, Sharon Stone's lowlife ex in Casino, a key player in the Watergate scandal in Nixon, and an unrepentant racist killer in Ghosts of Mississippi, which earned him a second Academy Award nomination — he essayed larger and more diverse roles on the small screen. He won two Emmys in a pair of TV-movies opposite James Garner — as a schizophrenic in Promise and the cofounder of Alcoholics Anonymous in My Name Is Bill W. — and he also played New York City Mayor Rudy Giuliani in an eponymous, post-9/11 telepic. Off screen, Woods' personal life seemed as intense as his roles. A twice-married ladies' man with an eye for pretty young things, he engaged in a very public war with Sean Young, his ex-girlfriend and costar in The Boost, whom he accused of harassment, and at age 59 dated 20-year-old starlet Ashley Madison, the daughter of one of his golfing buddies. He also claimed to have encountered two of the 9/11 hijackers on a flight in August of 2001. In 2006, Woods took on his first series-regular role as a crusading defense lawyer in Shark.