Britney Spears was 17 when she traded in her Mickey Mouse Club persona for a naughty-schoolgirl outfit in the music video for her first hit single, "Baby One More Time." Spears’ early days of swearing off sex until marriage didn’t last long, and it turned out that she wasn’t “that innocent.” “Smoking, drinking, sex—why is it such a big deal for me?” she proclaimed to People magazine in 2002. Soon she was gyrating in sexually charged music videos like "I'm a Slave for You" and making out with Madonna onstage at the 2003 MTV Video Music Awards. In 2005, when Spears was only 24 and at the height of her career, she had her first child, Sean Preston, with husband Kevin Federline. Controversy erupted when the young mother was photographed driving with her 4-month-old son in her lap. (She claimed she was being chased by paparazzi and didn’t have time to strap baby Sean into his car seat.) She gave birth to Jayden James Federline in September 2006, and filed for divorce from her husband two months later. Not long after the breakup, Spears started partying with Paris Hilton, drinking excessively, and unwittingly flashing the paparazzi while her babies were home with the nanny. Spears hit rock bottom in February 2007 when, in the midst of a very public nervous breakdown, she randomly shaved her head and subsequently checked into Malibu’s Promises rehab center. The next year was a rocky one—after failing to submit a drug test, Spears temporarily lost custody of her kids and was ordered by a judge to spend eight hours a week working with a “parenting coach” who supervised her interactions with Sean Preston and Jayden James. In an August 2008 interview with OK! magazine, Spears said she wanted her sons to have a “more normal childhood” than she had. It wasn’t until this spring that she regained primary custody of the boys after a three-year battle with Federline.

Hollywood’s Youngest Moms

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