Jason Alexander

On New Year's Eve 2003, Britney was in Las Vegas and had flown her childhood friend Jason Alexander out from her hometown of Kentwood, Louisiana, to celebrate the arrival of 2004.

Shocking the entire world, the pair tied the knot at the Little White Wedding Chapel during their trip to Sin City, but the union was annulled after just 55 hours.

At the time, Britney told E! News: "It was me being silly, being rebellious, and not really taking the responsibility of what I was doing, you know?”