Britney Spears and Jason Alexander
Length of marriage: 55 hours
Before the rehab stints, the head shaving and the court hearings, Britney Spears was America's pop princess. The virginal Southern sweetheart played into her public perception for nearly 10 years, until drugs, alcohol and a sudden disregard for reality sent her tumbling off her industry-fashioned pedestal. After a public breakup with Pop Charming, 'N Sync's Justin Timberlake, Spears' first highly public mishap was her 2004 marriage to childhood friend Jason Alexander in Las Vegas, a "till death do us part" that lasted all of 55 hours. Both Spears and Alexander claim the spirit of Sin City led them to the aisle of the Little White Wedding Chapel, but darker versions of an ecstasy-fueled bender trickled out no matter how much Spears' family or record label attempted to laugh the "incident" off. The marriage was annulled, but it would mark the beginning of one of the greatest falls from grace in pop history. But seven years and one additional divorce later (from Kevin Federline), Spears' career has barely blinked. Her latest album topped the charts as she embarked on a sold-out tour.