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More controversy arose when Spears declared that she would "remain a virgin until marriage".^[31] This pledge has been questioned britney spears sex photo due to her apparently sexual relationship with fellow pop singer Justin Timberlake.^[32][33]

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 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 britny spears nude photos 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,^{www.briney spears.com id="cite_ref-crossroads_56-0" class="reference">[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."^[62][63]