Year: 1994
Looks like celeb ladies had a thing for the Worm cause he managed to hook up with megastar and equally unique, Madonna back in '94. The relationship only lasted for two months but during the wildly publicized fling, Rodman claims the singer demanded that he impregnate her and tried multiple times. Dennis openly admitted later that he also thought her music sucked but that he could have married her if he wanted to. #badboysfinishfirst