Jennifer Lopez and Cris Judd
Length Of Marriage: 218 days
Some celebrities will rebound from a high-profile relationship by tying the knot with a minor celeb or civilian. Such was the case when, just a few months after splitting from Diddy, she married choreographer and musician Cris Judd. When Judd later won I'm a Celebrity, Get Me Out of Here!, the $200,000 prize went to the Make-a-Wish foundation. His, though, had already come true, as the three settlements with Lopez had made him a very rich man.