Madonna and Guy Ritchie
Never one to stand on tradition, it shouldn't have been a surprise to anyone when Madonna announced her pregnancy with then-boyfriend Guy Ritchie. Baby Rocco, born in 2000, was the second baby born to the unwed Material Girl. Madonna's first child, Lourdes, was fathered by the singer's personal-trainer boyfriend, Carlos Leon, in 1996. Ritchie and Madonna did wind up marrying four months after Rocco's birth, but the couple split in 2008.