Leonardo DiCaprio — Growing Pains to Oscar Winner

DiCaprio was Luke Brower on Growing Pains at 16. Three years later, What's Eating Gilbert Grape earned him his first Oscar nomination at 19. Titanic ($2.2 billion) made him the biggest movie star on Earth at 23. Then he spent 20 years chasing an Oscar through The Aviator, Blood Diamond, The Departed, and Django Unchained — finally winning for The Revenant in 2016. Net worth: $300 million. His environmental foundation has donated $100 million+. The teen heartthrob became one of the most serious actors of his generation by sheer force of choosing difficult roles over easy paychecks.