Length of marriage: Nine days
There are bad decisions and worse decisions, and then there are Dennis Rodman's decisions. The seven-time NBA rebounding champion, who helped the Chicago Bulls win five titles, wore a wedding dress to a book signing for the release of his 1996 autobiography. Much like his eye-catching fashion choices, when Rodman married Baywatch beauty Carmen Electra in a 7 a.m. Las Vegas ceremony in 1998, the news turned a few heads. His publicist questioned the legality of the marriage, saying Rodman may have been "deeply intoxicated" at the time. For their part, the couple said their love was legit until nine days later, when they filed for an annulment. The marriage officially ended six months later. Reflecting on the quickie wedding, Electra told People, "It's easy to get caught up in a moment. You think it's romantic, but then you realize, 'God, we did it in Vegas?' It's like getting a cheeseburger at a fast-food restaurant."