Gallery: Celebrity Trainwreck Marriages 2 of 15
Britney Spears & Jason Allen Alexander
Image: Getty Images
Before the K-Fed days, Britney had actually married her childhood friend, Jason Alexander (no, not the one from Seinfeld). The couple married at Las Vegas' Little White Wedding Chapel in 2004, but were married for less than three days. The union was annulled after 55 hours.