Bill Hader will put up with a lot: he ground out 20-hour days as a production assistant on movie sets when he first moved to Los Angeles after college, getting coffee and babysitting actors; he suffered panic attacks on stage when he eventually made it on to Saturday Night Live and managed to finish a skit when a migraine left him temporarily blind; now, he works four jobs on his HBO smash-hit Barry, which just wrapped its second critically acclaimed season. But one thing that Hader will absolutely not tolerate is Hollywood impertinence.

While on Saturday Night Live in the early aughts, honing impressions and giving life to characters like underground-club-king Stephon and talk show host Vinnie Vedecci, Hader was quietly crafting a film career. He didn’t care if he owned a scene — he just wanted to be part of “something good.” So when he read the part of a ludicrous-but-loveable cop in an upcoming Judd Apatow flick called Superbad, which became Hader’s big-screen breakout moment, he jumped, passing on a bigger part in a projected blockbuster with an underwhelming script. “I got a very snarky email from this agent that said, ‘Let me get this straight: instead of being with this big actor in a lead role for this big amount of money, you want to be with the kid who plays George Michael on Arrested Development for that amount of money — and you’re playing Cop Number Two?’” explains Hader, now 41. “I didn’t respond because, well, it was rude.”

Instead, he waited patiently for months for both movies to hit theatres in 2007. “When Superbad was a massive hit and the other wasn’t, I found the email and I just responded, ‘yes.’”

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Hader grew up in Tulsa, Oklahoma. He wasn’t a great student, probably because he got unmanageably anxious before tests. (He once said he just wrote his name on his SATs and left). Instead, he watched movies and dreamed of becoming a director. After a stint at community college, Hader, with nothing to lose, moved to Los Angeles in 1999. He got a job as a production assistant, working dispiritedly on movies like Spider-Man and VH1’s The Surreal Life. Then, after nearly falling asleep at the wheel after a hellish day filming The Scorpion King, The Rock’s first leading role, Hader realized he needed to reimagine his life. He quit and signed up for improv classes with friends.

This simultaneous coupling of aimlessness and burning creative drive might feel familiar for fans of Barry, the masterful HBO tragicomedy Hader created, stars in, writes, and directs — and which is nominated for a staggering 17 Emmy awards this month, including best lead actor in a comedy series. (Hader won that award last year. When asked how he can possibly keep outpacing his own success, he just laughs: Yep, we really fucked ourselves!”) The titular character in Barry, played by Hader, is a repentant hit man who was lured into the game after a tour in Afghanistan. When he almost-accidentally enrolls in an acting class while tracking a mark, he gets hooked on the craft.

“[Before Superbad] I got a snarky email from this agent that said, ‘You want to be playing Cop Number Two with the kid from Arrested Development?’”

The improv captured Hader, too. So in 2003, he and friend Matt Offerman, along with another couple of buddies, started doing a show in a backyard in Van Nuys, California. “I didn’t have an agent, or headshots or a manager,” says Hader. “We were doing shows in a backyard while everyone else was trying to get the HBO Showcase space because managers would come see you. My friends and I were almost purposefully doing alternative-comedy.” Except word got out anyway: Matt’s brother, actor Nick Offerman of Parks and Rec, went to a show with his wife, comedian Megan Mullally. “And then I just got obscenely lucky,” says Hader casually. Mullally called legendary SNL showrunner Lorne Michaels and got Hader a meeting, which turned into an audition, which turned into an eight-year comedy marathon.

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When Hader got the call in 2005 to join SNL, walking onto the same stage as his idols like Eddie Murphy, he was crewing for Iron Chef America. This is a distinctly insane origin story: becoming a cast member is supposedly reserved for those who have built fame by rising through the ranks of prestigious improv troupes like Groundlings and Second City. But in retrospect, now faced with his body of work which presents a complicated and more interesting model for a modern leading man — an underdog who isn’t insecure, a laidback guy who works his ass off, a comedian who makes you laugh without actually telling a joke — Hader’s rise doesn’t seem all that surprising at all.

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Despite his critical success, the anxiety Hader had been swallowing since childhood quickly began to eat away at him during his turn as an SNL cast member. He stopped sleeping for nights at a time. “I liked the SNL experience in retrospect, but while it was happening, I was pretty terrified,” says Hader with a sheepish laugh. “I had a rough time getting through it; you know, the fact that you just had one shot and if you messed it up, everyone would see.” Even though Michaels told him he could work at the show forever in an attempt to quell his nerves, Hader suffered a full panic attack onstage while playing Julian Assange in 2010.

“But every season I got a little bit better — and it was Saturday Night Live and I didn’t want to lose that, you know?” he says. So he shuttled back and forth between coasts as he and his then-wife, filmmaker Maggie Carey, tried to balance work and a growing family. (They divorced last year and have three daughters together, aged 9, 7 and 4.)

When he announced his retirement from the show, it felt right. “Finally,” he says, “there was no anxiety.” Right out of the gate, Apatow called, hoping to cast him as a love interest for Amy Schumer in the deeply hilarious Trainwreck. “I was ecstatic that Judd happened to be looking for someone you would not normally see in a romantic comedy, and I was like, ‘Well, then, I’m definitely your man!’”

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Hader might be the only person who doesn’t see himself as a leading man. Standing well over 6 feet, with a relaxed laugh, razor-sharp cheekbones and running-back shoulders, Hader is diminutive only in ego. “Maybe it’s because I’m from Oklahoma or something,” he says, explaining that, much like rudeness, being a braggart is kind of a midwestern character flaw.

The notion of an unlikely leading man is what led him to the concept behind Barry. “There is something in pop culture that says hit men are always very masculine and very cool and I am neither of those things,” he explains. “I wondered what it would be like if I played one and got very real about trying to deal with it. I would probably be suicidal, I thought, because I would be so sad about being able to do it. It brought up interesting questions.”

“Growing up, there was this feeling that you had to be aggressive to get the things you want and that, as a man, you’re always on the offensive, starting fights. I always thought the whole thing was kind of silly.”

Despite the fact that the show is branded as a comedy, Hader adeptly uses it to explore ideas of masculinity, kicking at the cracks in the gun-wielding aggressive machismo that has swept popular culture. (He, for instance, can’t deal with Donald Trump’s one-sided hollering: “Even my four-year-old knows that man is rude.”) It’s more interesting, reasons Hader, to present life as it really is: muddy, confusing, complicated. Epic fight scenes in Barry aren’t juiced up with pulse-pounding musical scores; they’re served up bare for the audience to mull over, with only the thumping of bodies or whirring of bullets to punctuate the pain. “Growing up, there was this feeling that you had to be aggressive to get things you want and that, as a man, you’re always on the offensive, starting fights or whatever the hell it might be,” says Hader. “I always thought the whole thing was kind of silly. I just didn’t understand it when I would hear people talking about romantic versions of a fight they were in or how they fucked someone over.” Hader isn’t afraid to admit that he has no idea what makes someone a good person these days, but he’s pretty sure it has something to do with empathy.

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Given his impatience with bloodshed, it’s initially surprising that Hader signed on alongside Jessica Chastain to star in the horror sequel It: Chapter Two, which is based on the classic Stephen King novel and hits theatres this month. But this isn’t a “by-the-numbers” movie about violence, says Hader. “I don’t like anything where people are getting murdered with a knife. I’m not into torture. There is something that is weirdly fetishistic about it,” he explains. A good monster movie, he argues, actually grapples with deep issues, rather than slashing away at surface banalities. It is about trauma, in the same way that recent tour-de-force horror film Get Out was about racial prejudice and It Follows unpacked bias against promiscuity. “When you can take these concepts and put them in a horror context,” says Hader, “it’s exciting.”

It’s also proof that Hader, practiced improviser and Midwestern good guy, really is all about the pitch. A bad one, like that graceless jab at Superbad, can turn him off. A good one can get him to do anything, explore parts of himself he never thought he’d turn to on camera. Which is how he ended up in It: Chapter Two in the first place. Finn Wolfhard, the 16-year-old Canadian star of Stranger Things who played the young Richie Tozier in the first It film was quoted in the press saying he wanted Hader to play him in the next film. Then Hader’s phone rang: director Andrés Muschietti wanted to have lunch. “I was just like, ‘Wow,’” Hader says, “that kid is really powerful.”

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