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Rihanna

Current age: 25

Career at 20: Days after her 20th birthday in Feburary 2008, Rihanna attended the Grammys, where she presented and won the award for best rap/sung collaboration with Jay Z for "Umbrella." That year, she also joined Kanye West, Lupe Fiasco, N.E.R.D., and Nas for the Glow in the Dark Tour. She also released several successful singles, including "Disturbia" and "Take a Bow."

Relationship status at 20: Rihanna was in a relationship with Chris Brown when she turned 20 in 2008, and he joined her for several stops on the Glow in the Dark Tour. The two broke up just after her 21st birthday in February 2009 as reports surfaced of assault.

Quoted at 20: Rihanna sat down with Cosmopolitan in 2008, where she talked about her success and how it helped her confidence. "A year ago, I would have sat here in my shell with my hands in my lap and been very shy. But now, I can be goofy and outgoing." Later, she said, "Some people never figure themselves out, and that's sad. I'm still learning who I am, but I'm not scared to be myself anymore."

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