Britney Spears

Current age: 31

Career at 20: Britney Spears celebrated her 20th birthday in December 2001, just after the release of the Britney album and the start of her Dream Within a Dream tour. In 2002, her movie Crossroads was released, and she was back in the studio recording her next album, In the Zone, at the end of the year.

Relationship status at 20: Britney and then-*NSYNC member Justin Timberlake broke up in 2002 after dating for nearly three years, and he went on to release "Cry Me a River" in November of that year, which is rumored to be about Britney cheating on him.

Quoted at 20: In October 2002, Britney opened up about fame in Rolling Stone, saying, "I feel changed. I'm a little more serious than I was. It's really weird, because you're a star, and everything is about you all the time — and I'm tired of that. I want to have a different perspective. And not have all my family and all the people I know working for me. I want to hang out with my friends and be a nobody. Because that's how you become reinspired."

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