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Made headlines for partying, and in February, for spontaneously shaving her head. |
2007 |
Announced in May, after rumors had swirled for months, that she and hubby Kevin were expecting their second baby.
Second son Jayden James was born in September, and in November she announced she was divorcing Kevin Federline.
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2006 |
After weeks of media speculation, the pop princess finally announced her pregnancy to the public.
Debuted reality show, "Chaotic," featuring behind-the-scenes footage of married life with Kevin Federline.
Gave birth to first child, Sean Preston, in September.
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2005 |
Shocked fans by marrying childhood pal Jason Allen Alexander in Las Vegas; marriage was annulled 2 days later.
Married dancer Kevin Federline at a surprise ceremony in Studio City, CA.
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2004 |
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Made headlines by kissing Madonna on the lips during a performance at the 2003 MTV Video Music Awards.
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2003 |
Played the lead role in 'Crossroads,' a teen flick about childhood friends who go on a road trip.
Broke up with Justin Timberlake.
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2002 |
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Her song "Oops! ...I Did It Again!" entered pop culture.
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2000 |
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Began dating *NSYNC member and former Mouseketeer Justin Timberlake.
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1999 |
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Released her first single, "Baby One More Time."
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1998 |
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Signed a contract with Jive Records.
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1997 |
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Landed a spot in the Disney Channel's "Mickey Mouse Club."
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1993 |
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Competed on "Star Search"; her first performance was a winner.
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1992 |
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Moved to New York City with mother and sister.
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1991 |
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Began taking dance lessons.
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1987 |
| Born in Kentwood, Louisiana on December 2.
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1981 |
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 © 2007 Matthew Simmons / Getty Images |
