Surprising Celebrity Hookups (20 images)

The unusual duo dated in 2002, after meeting at the Grammys. Despite McConaughey saying they were "just friends", Jackson admitted to the fling.

The unusual duo dated in 2002, after meeting at the Grammys. Despite McConaughey saying they were "just friends", Jackson admitted to the fling.

The unusual duo dated in 2002, after meeting at the Grammys. Despite McConaughey saying they were "just friends", Jackson admitted to the fling.

The notorious playboy and the "A Thousand Miles" singer dated on and off for about a year in 2002.

The notorious playboy and the "A Thousand Miles" singer dated on and off for about a year in 2002.

The notorious playboy and the "A Thousand Miles" singer dated on and off for about a year in 2002.

The actors dated briefly in 2007

The actors dated briefly in 2007

The actors dated briefly in 2007

The two briefly dated in 1986, when meeting on set of the film "Lucas". Sheen claims to have given Ryder her stage name (original name is Winona Horowitz).

The two briefly dated in 1986, when meeting on set of the film "Lucas". Sheen claims to have given Ryder her stage name (original name is Winona Horowitz).

The two briefly dated in 1986, when meeting on set of the film "Lucas". Sheen claims to have given Ryder her stage name (original name is Winona Horowitz).