In February 2002, Spears made her acting debut in the Paramount Pictures drama film Crossroads which starred her sister, who portrayed the central character Lucy Wagner. Spears made a cameo, playing the younger version of Britney’s character. Following Crossroads, Nickelodeon cast Spears as a regular performer in the eighth season of the sketch comedy series All That. The season followed a two-year hiatus of the series. Spears portrayed various roles through the two seasons she appeared in as well as herself. Spears’s performance received positive reviews from critics with many complimenting her comedic timing and being a highlight of the show. Spears did not return for the series’ tenth and final season to pursue other roles on the network. Spears made a guest appearance at Stars, Stripes and Skates skating gala at Madison Square Garden in September 2002.

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