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Marcelo Krasilcic
Coat by Hugo; sweater and jeans by Boss.

For many, Bill Hader was the only reason to watch SNL from 2005 to 2013. He had that Phil Hartman–like ability to salvage a skit in a supporting role with trademark characters including Stefon and elderly reporter Herb Welch. But it was his performance opposite Amy Schumer in Trainwreck that showed his depth as an unlikely leading man.

Hader's easy Midwestern charm—reminiscent of Jimmy Stewart—made the movie work; he's an under-stated Everyman, not too handsome, not too goofy. He can be sidesplittingly funny doing shtick on Conan and Kimmel, thoughtful and unpretentious talking about Kurosawa for the Criterion Collection.

He does drama (The Skeleton Twins) and writes (South Park; Documentary Now!), but what he's really always wanted to do is direct. "I've been movie-obsessed my whole life," says Hader. All of which makes Barry, a HBO series he co-created with Alec Berg (Curb Your Enthusiasm), all the more intriguing. Hader, who directed the first three episodes, stars as a Marine turned hit man who follows a target to an L.A. acting class run by Henry Winkler and ultimately signs up.

The only thing Hader doesn't love about directing is having to watch himself act. Then again, it took five seasons at SNL for him to feel like he wasn't auditioning every weekend. That's when Lorne Michaels told him, "You know you don't have to worry. Have fun."