Kieran Culkin

He was the bed-wetting cousin in Home Alone, not a launching pad. He spent years being quietly good in things like Igby Goes Down, which earned him a Golden Globe nomination in 2002 and not much lasting attention. The career break came when the Succession producers sent him the script to read for Cousin Greg. He passed, lobbied for Roman Roy instead, and built a character out of a man who uses cruelty as a substitute for a personality. HBO let him improvise freely and refuse to stand on his mark. He made Roman Roy feel like someone you might actually know, which is the worst possible version of a compliment.

The 2024-2025 awards cycle turned him into something close to inescapable. He won the Emmy and the Golden Globe for Succession, delivered a "Suck it, Pedro" speech that spread everywhere, and used the Emmy podium to ask his wife for a third child on live television. Then A Real Pain got him back into movie theaters, and he did it again. The 2025 Oscar for Best Supporting Actor made him the first actor since Christopher Plummer to win that category from a film not nominated for Best Picture. His wife's public take: "the most hardworking but also somehow the least ambitious person I've ever known." The speeches are negotiating sessions. The trophies are leverage.

He met Jazz Charton in a New York bar by mocking her name to her face. She liked it. They got married in Iowa during a road trip, in a storm, in 2013. The award speeches have become a recurring bit: he asked Jazz for a third child from the Emmy stage, and she'd reportedly promised him four if he won an Oscar. He won. None of it looks like a plan. That's probably the point.