Jack Nicholson

Whether playing a loser or a lothario, a heavy or a hero, this iconic actor is always, on some level, Jack Nicholson. That's not to imply that he isn't versatile. In the '60s the hungry up-and-comer turned in a bunch of offbeat performances in a string of cheapie flicks, a few of which he wrote. He was over 30 when he earned his first of many Oscar nods — not to mention an expanded fan base — as a disgruntled lawyer in 1969's Easy Rider. In the '70s Nicholson tapped into the decade's unrest by essaying a slew of unforgettable roles in legendary films: a rebel in Five Easy Pieces, a misogynist in Carnal Knowledge, a lovesick gumshoe in Chinatown and an unruly inmate in One Flew Over the Cuckoo's Nest, which snagged Nicholson his first Academy Award. He became a scenery-chewing, eyebrow-arching megastar in the '80s, delivering broad (sometimes to the point of parody) yet always interesting performances in more commercial fare (Terms of Endearment, The Witches of Eastwick, Batman). Nicholson's personal life — particularly where women were concerned — was as dramatic as his career. At the age of 37, he learned that the woman whom he thought was his mother was actually his grandmother and that his supposed sister was his biological mom. As for his own romantic entanglements, he had a longtime on-again, off-again relationship with Anjelica Huston that ended acrimoniously in 1990 when he fathered a child with starlet Rebecca Broussard, and later he was linked to the much younger Lara Flynn Boyle. In the late '90s the sexagenarian actor started to slow down. He took a four-year hiatus from the big screen after his Oscar-winning turn as a surly obsessive-compulsive writer in 1997's As Good as It Gets. But he was still a ubiquitous industry presence, frequently spotted on red carpets and at Lakers' games, almost always sporting his trademark dark sunglasses.