Jack Nicholson and Anjelica Huston

celebrity couples

It was 1973. Jack was one of Hollywood’s most notorious lady-killers and Anjelica was the lanky daughter of legendary director John Huston (The Maltese Falcon). They met at a nightclub, sparks flew, and the Voguemodel-turned-actress found herself embroiled in a love affair with Nicholson that lasted sixteen years. The Oscar-winners became one of celebdom’s most enduring, glamorous couples — until 1989, when the eternal philanderer got his mistress pregnant (allegedly, theSmash star beat him up when she found out). They parted ways, but in 2011, Jack told The Daily Mail that their breakup left him shattered. “I was annihilated emotionally by the separation from Anjelica. It was the toughest period of my life.” Should’ve kept it in your pants, playboy.