- 1993-1994
Mini-Mouse Pack
Spears, 11, lands a cast spot on the New Mickey MouseClub, where she performs with Christina Aguilera, Ryan Gosling and Justin Timberlake. Timberlake will later become her first public romance.- 1998
Proper Dress Code
Spears releases the video for ". . . Baby One More Time," in which she wears a schoolgirl's uniform and knotted shirt, revealing her midriff. "The outfits looked kind of dorky, so I was like, 'Let's tie up our shirts and be cute,'" she tells PEOPLE. The following spring, Spears, 17, poses in hot pants and a push-up bra for her first Rolling Stone cover.- 2000
Like Mother, Like Daughter
After losing the Best New Artist Grammy award to pop rival Christina Aguilera, Spears and her mom release a coauthored memoir, Heart to Heart. "I'm living proof that you can succeed, no matter where you're from or how little you have," she writes. The two write another book together, A Mother's Gift, released in 2001.Oops! Brit Does it Again
Spears' album, Oops! … I Did It Again debuts at No. 1 and sells more than 1 million copies in its first week. The title track touts the now-famous lyrics "I'm not that innocent."
Pop Power Couple
Spears and singer Timberlake go public with their romance when they sit together at the MTV Video Music Awards in New York. During the show, Spears performs a medley of her hit "Oops!...I Did It Again" and "Satisfaction" in a sequined, flesh-colored outfit.- 2001
Snake on a Pop Star
Spears drapes a 7-ft. albino python around her shoulders during a performance of "I'm a Slave 4 U" at the MTV Video Music Awards. The python is so "sticky" and "slimy," she tells EW, that she breaks into hives after she touches it the first time. Her third album,Britney, makes her the first female artist to have three albums debut at No. 1.- 2002
Bye-Bye-Bye
Ending weeks of speculation, Spears confirms that she and Timberlake are no longer seeing each other. "[The breakup] was horrible. Very upsetting and it took a lot out of me. He was my first real love, and I doubt I'll ever be able to love anyone like that ever again," Spears tells PEOPLE. "But I'd rather spend two days with my soulmate than the rest of my life with some guy who doesn't mean as much."- 2003
'I'm Not That Innocent'
In a W magazine cover story, Spears poses like a designer-clad lap dancer, and admits to kissing actorColin Farrell and losing her much publicized virginity to Timberlake. "I thought he was the one," the pop star says to the magazine. "But I was wrong!" On August 28, the pop princess and her pop peer Aguilera famouslykiss pop queen Madonna during a performance at the MTV Video Music Awards.
Sweet Success
Spears releases her album In The Zone, and the single "Toxic" goes on to win a Grammy for best dance recording. Despite her commercial success, this is Spears' first Grammy win.- 2004
Vegas Style
Spears weds childhood friend Jason Alexander in a Las Vegas ceremony, but the marriage is annulled after 55 hours. Spears tells Today's Matt Lauer it was an act of rebellion, prompted by a demanding performance schedule.
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