Ben Affleck

He and Matt Damon wrote Good Will Hunting in their early twenties, two kids from Cambridge with no real credits and a script nobody wanted to make. When it finally got produced, Affleck walked away with the Oscar for Best Original Screenplay at 25, still the youngest person to win that award. He wrote it because he needed a good role, which is either very cynical or very smart, depending on how you look at it.

Gigli made $7 million on a $75 million budget in 2003. Daredevil came out the same year. The tabloids coined 'Bennifer.' Most careers don't survive one of those, and he survived all three. He rebuilt as a director: Argo won Best Picture in 2013, but the Academy didn't even nominate him for Best Director. He married Jennifer Lopez in 2022, almost two decades after their first engagement ended. The divorce was finalized in February 2025. Running Artists Equity keeps him from having to explain what comes next.

Gigli was a disaster, but Affleck has called it 'a gift.' Without it, he says, he might never have directed. Gone Baby Gone (2007), The Town (2010), and Argo followed, and that's the part of his resume that holds up best. He's completed residential treatment for alcoholism three times (2001, 2017, 2018) and talked about it more candidly than most people in his position. James Gunn has reportedly met with him about directing a DC film. Affleck keeps saying no.