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November 2004 saw the release of her first greatest hits collection, Greatest Hits: My Prerogative, which features all of Spears's singles with the exception of "From britney spears oops The Bottom Of My Broken Heart". It also featured three previously unreleased songs, them being a cover version of American R&B singer Bobby Brown's 1988 hit "My Prerogative", "Do Somethin'", produced by Bloodshy and Avant, whom she had worked with on In The Zone, and "I've Just Begun (Havin' My Fun)", which was a song recorded for Spears's fourth album, In The Zone, but did not make the final cut.^[86] By the end of that year, Spears had become one of the best-selling artists in the world.

Spears had her first starring role in the 2002 film Crossroads,^[57] in which she portrayed a high school graduate who travels to find her long-lost mother. The movie was poorly received,^[58] as was her performance; Spears received Razzie Awards for Worst Actress and for Worst Original Song.^[59] Nonetheless, the film grossed over $60 million worldwide.^[60] Spears also made cameo appearances in Austin Powers in Goldmember and Longshot.^[61] Footage of Spears appeared in the 2004 documentary Fahrenheit 9/11, which samples a 2003 CNN interview about the Iraq War in which Spears says, "Honestly, I think we should just trust our president in every decision he makes and should just support that, you know, and be faithful in what happens."^{britney spears sex id="cite_ref-61" class="reference">[62]}^[63]

Spears initially supported the policies of President Bush in a CNN interview in 2003 with conservative political pundit Tucker Carlson. However, her support was not due to politics; instead more to show patriotism. Carlson praised Spears for her support of the president, who was unpopular at that time among Hollywood britney sprears sex tape entertainers.^[70]