At this time Spears announced she would take a career break; she released a greatest hits collection. In 2005 Spears released an album of remixes.

In May 2006 Spears announced her second pregnancy on "The Late Show with David Letterman" and appeared on the news magazine show "Dateline." After the interview aired, Spears posed nude for Harper’s Bazaar magazine cover and gave birth to a second son, Jayden James Federline in September. In November Spears filed for divorce from Federline citing irreconcilable differences. Magazines like People, Star Magazine, In Touch magazine and other women’s magazines chronicled Spears’ troubles and continue to devote coverage to her.

In February 2007 Spears seemed to hit a low point when she shaved her head. Paparazzi captured the entire coiffe-crisis and photos of Britney mid-shave appeared in countless celebrity magazines like People, Us Weekly and InTouch magazine. Even magazines like Time magazine covered Spears’ troubles, called Spears "former pop star, current tabloid staple."

In October 2007 Spears released the album Blackout, which received lukewarm reviews and debuted at number two on the U.S. Billboard 200. Her single, "Gimme More" quickly peaked at number three on the Billboard Hot 100 chart but Spears highly-anticipated comeback performance of the single was nothing short of a major embarrassment. In the performance Spears was sluggish and out of sync with her lip-synching. The embarrassing performance prompted Jive Records to cancel all live promotion.

For the next year Spears continued to have custody troubles and legal troubles involving minor car accidents and driving without a license. During this time she fired her longtime manager and body guard; her personal publicist resigned. Due to a series of bizarre behavior including shaving her head and attacking a car with an umbrella in a fit of rage and missed court dates Spears lost custody of her children. Finally Spears’ family stepped in to rescue the singer from her seemingly self-destructive path. People Magazine has reported that Spears is currently back in the studio working on a new album.

People.com also recently reported that Spears and her ex-husband Federline have come to a custody agreement—Federline will retain sole legal and physical custody while Spears will have visitation rights.

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