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Britney Spears's fourth album, In the Zone, was released on November 18, 2003. Jettisoning the Max Martin produced synth pop of her earlier releases, the album takes in lesser-known producers such as RedZone as well as such big names as Moby and R. Kelly. Spears co-wrote eight of the album's thirteen songs. The first single, "Me Against the Music" (featuring Madonna), while a staple on MTV's Total Request Live, fared less well on the Billboard Hot 100 chart, though it performed well on other charts. The second single, "Toxic", was released on March 1, 2004.

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.

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.