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On Saturday, January 3, 2004, Britney Spears married her childhood friend Jason Allen Alexander at The Little White Wedding Chapel on the Las Vegas Strip in Las Vegas, Nevada. The couple promptly arranged for an annulment, which occurred on Monday, January 5, 2004, ending their 55-hour marriage.

In June 2002, Spears branched out as a restaurateur with the opening of a New York City eatery, NYLA, but the venture was not a success and the restaurant closed in 2003. Her appearance in the movie Crossroads, which reached number two in the box office charts, netted her a Razzie Award for worst performance of 2002.

Britney Spears's castmates on the show included Justin Timberlake and Joshua Chasez (who later became members of the pop band NSYNC), Keri Russell (star of the TV show Felicity) and Christina Aguilera, also a pop singer. Spears dated Timberlake for about five years.