1993-1994

Britney Spears

Mini-Mouse Pack

Spears lands a cast spot on The New Mickey Mouse Club, where she performs with Christina Aguilera, Ryan Gosling and Justin Timberlake. Timberlake will later become her first public romance.

1998

Britney Spears

November

Proper Dress Code

Spears releases ". . . Baby One More Time," and in the video wears a Catholic 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. "What's the big deal?" she asks the magazine. "I have really strong morals, and just because I look sexy on the cover of Rolling Stone doesn't mean I'm a naughty girl."

2000

February 23

Grammy Disappointment

Spears performs at the Grammys but loses the Best New Artist award to Christina Aguilera.

Britney Spears

May 09

Like Mother, Like Daughter

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 in her book. The two write another book together, A Mother's Gift, released in 2001.

May 16

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," and the song "Lucky" tells the story of a famous but lonely Hollywood star. In June she launches her first world tour of the same name.

Britney Spears

September 07

Power Couple

Spears and singer Timberlake go public with their romance when they sit together at the MTV Video Music Awards. During the show, Spears performs her hit "Oops!...I Did It Again" in a sequined, flesh-colored outfit.

2001

Britney Spears

September 06

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 PEOPLE, 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

Britney Spears

March

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

August

'I'm Not That Innocent'

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!"

Britney Spears

September 06

Shock Value

The pop princess and her pop peer Aguilera famously kiss pop queen Madonna during a performance at the MTV Video Music Awards.

Photo Credits

BIOGRAPHY (top to bottom): Everett/Rex USA; Kevin Mazur/Wireimage; Delacorte Press; Kevin Mazur; Beth Keiser/AP; TAMMIE ARROYO/AFF; Julie Jacobson/AP

Edited by Mai Dinh, Janet Murphy