A marriage doesn’t have to last a long time to give a guy a big payoff at the end of it. Cris Judd married Jennifer Lopez in September 2001 after a whirlwind courtship. The actor/dancer met Lopez in Spain when he was hired to direct her video for “Love Don’t Cost a Thing,” and they had instant chemistry. Unfortunately, instant chemistry isn’t enough to keep a marriage going, and they split up in June 2002. Judd took away a massive settlement from Lopez, with reports saying that he got about $14 million for nine months of matrimony.