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Leonardo DiCaprio

Current age: 41

Career at 20: Leo had already established himself pretty well in Hollywood, even as a teenager. In fact, just before his 20th birthday, he received a best supporting actor Oscar nomination for his role in What's Eating Gilbert Grape.

Relationship status at 20: Leo was often seen out and about with model Bridget Hall, though their relationship was never confirmed.

Quoted at 20: Leo appeared on the Today show in 1995, where he commented about fame: "Definitely not what I expected, you know? You work so hard to be in this place, and then once you're there, it's sort of like, it's shocking to be there. . . . It's not as glamorous as you expected it to be, but that's an old cliché, I suppose. I'm enjoying it, you know, having a good time. I'm just going to try to do as much good work at this point in my life as possible."

Image Source: Getty / SGranitz
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