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.
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.
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."
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.
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.
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."
In a W magazine cover story, Spears poses like a designer-clad lap dancer, and admits to kissing actor Colin 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 famously kiss pop queen Madonna during a performance at the MTV Video Music Awards.
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.
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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