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14. Leonardo DiCaprio
We love a picture of baby Leo, and by baby we mean 25 years old (he does look super young though, don't you think?).

Leo's first recurring role was on Growing Pains, and while it didn't last long, it paved the way for more roles to come. In 1993, he starred in What's Eating Gilbert Grape opposite Johnny Depp, and earned himself both an Academy Award and a Golden Globe nomination. Once he hit his 20s, he kept acting in hit after hit, including Titanic of course.