Married from 1985 to 1989, they also costarred in Shanghai Surprise in '86.

The president's son was reportedly a rebound for Madge after her marriage to Sean Penn.

"She wanted to get married and have a child with me," the MLB star once said of an encounter that took place in 1991, when he was married. Hmm.

Rodman said the two were together from 1993 to 1994.

Beatty didn't just direct 'Dick Tracy'—he also starred in it alongside Madonna. The 21-year age gap between the pair did nothing to deter a supposedly super steamy fling.

Madonna's 1992 photography book Sex featured her engaging in a threesome with Kane and Naomi Campbell. It was fake, and Kane says he and Madge never got together, but it was steamy nonetheless.

The "Ice Ice Baby" singer said he broke up with Madonna over the Sex book—but that she was a "great lover."

The music-industry giants reportedly hit it off shortly before Pac's 1996 murder.

The two shared an artistically fruitful relationship before the painter's death at the age of 27.

Married from 2000 to 2008, they had a son in 2000 and adopted another in 2006.

Madonna and her personal trainer were together for a couple years in the mid-'90s. Together they had a daughter, Lourdes, who turned 18 last year.

An affair with Madonna was rumored to be the reason Rodriguez's wife of six years—and mother of his two children—filed for divorce in 2008.