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Matt Damon

Current age: 43

Career at 20: Matt was barely making a dent in the film industry at 20 but managed to land a role in School Ties. Within the next five years, though, Matt got plenty more roles and even won an Oscar for the Good Will Hunting screenplay, which he penned with Ben Affleck.

Relationship status at 20: Not a lot is known about Matt's earlier relationships, but his love life was thrown into the public eye when he started dating Minnie Driver, whom he met on the set of Good Will Hunting.

Quoted at 20: When reflecting back on being a young actor, Matt shared an interesting tidbit during an Esquire interview: "My mother thought it was child abuse. She literally did. She was a professor who specialized in early childhood development, and she thought putting a child on stage or in a commercial or in a movie was child abuse."

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