George Clooney has a theory: “There is never a bad time to talk about the insanity of war.” That’s why he said yes to Hulu’s Catch-22 remake (premiering May 17), despite his original reaction to the idea, which was “F—, no. I wouldn’t touch it with a 10-foot pole.” Clooney’s wariness stemmed from several factors, not least of which was Catch-22‘s legacy. Joseph Heller’s 1961 novel, which follows John Yossarian, a young bombardier in World War II, is regarded as a classic, and was memorably adapted for the big screen by Mike Nichols (Working Girl, The Birdcage) in 1970 with stars Alan Arkin and Martin Balsam. And even for those not familiar with the book or film, odds are they know the phrase itself, which entered the lexicon after its publication.

A catch-22 is, essentially, an endless, inescapable loop. For Yossarian, it means he’s trapped in a war. “The catch-22 is that the only way you can get out of the military is if you’re crazy, but if you know enough to say you’re crazy, then you’re not crazy,” Clooney explains. That’s the central idea of Heller’s extremely complicated story, which jumps between various character perspectives. “It’s a dense, kaleidoscopic novel that does not follow any particular linear shape or structure,” executive producer Luke Davies says. Which is precisely why it took Davies and his co-writer David Michôd nine months to complete even just the outline for the story, which they ultimately decided would work best in the format of a six-episode miniseries.

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By the time Clooney read the scripts, he couldn’t turn the project away. “They did such a beautiful job,” says the 57-year-old actor-director-producer. “So we thought, ‘Well, s—, I guess we’re going to be doing Catch-22 now.'” Clooney and his producing partner Grant Heslov — who each directed two episodes, as did Ellen Kuras — then set out to discover their Yossarian and found him in Christopher Abbott, best known for his work on HBO’s Girls. “I didn’t know him when he came in to read, and he just blew us away,” Clooney says. “He can break your heart and he can do comedy. That’s rare.”

Abbott has to flex both muscles as Yossarian, a sane man in a world of people who are either insane or not paying attention. “It’s the tail end of the war, and he’s noticing that they’re sending guys out on these missions, and all he’s saying is ‘Why?'” Abbott says. Yossarian asks that question many times throughout the series as his mission count — the very thing he must complete in order to go home — keeps rising. “He constantly feels like he’s screaming down an empty hallway,” says the 33-year-old Connecticut native. “He feels very alone. He doesn’t understand how his friends are so willing to give their life over to something that he thinks is essentially inane.”

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But this isn’t a commentary on war. It’s a commentary on the bureaucracy of war. And in Yossarian’s case, his enemies aren’t the German soldiers he’s bombing, but rather the people preventing him from going home. For much of the series, that’s Colonel Cathcart, the man responsible for raising Yossarian’s mission count time and time again.

Clooney himself was originally set to play Cathcart, but as a producer and a director, he had enough on his plate. That’s when Clooney thought of Kyle Chandler, with whom he’d worked on 2012’s Oscar winner Argo. “The thing about Kyle is there’s never a moment where he’s on camera that you don’t believe him,” Clooney says. “And I’ve never seen him do anything like this.” In this role, Chandler leaves behind the heartwarming sincerity with which he once delivered Coach Taylor’s epic locker-room pep talks on Friday Night Lights for a man who is anything but a mentor to Yossarian. “Cathcart is representing everything that is absolutely insane about the situation at hand,” Chandler, 53, says. “This war turns people, and I think he just went mad.” And if Cathcart isn’t the one risking Yossarian’s life, it’s Lieutenant Scheisskopf—a smaller role that Clooney felt he could tackle—who’s upping the mission count. And above him, there’s General Dreedle (Peter Guinness). As Clooney puts it, “S— rolls downhill.” And for Yossarian, that means his nightmare has no end.

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But Heller’s novel isn’t revered simply for the tragedy in its tale. It’s also an extremely satirical look at the absurdity of war. All of which is to say: It’s funny. It’s really, really funny. “There is one insanely ridiculous scene where I tell Chris to drop his pants, I want to see his balls,” Clooney says. “That’s not something I’ve ever said in a film before.” Furthermore, Chandler recalls reading an introduction to the book written by former Virginia senator Jim Webb. “He was in Vietnam and there was a lull in a battle, and he hears one of his buddies laughing his ass off in a foxhole across the way,” Chandler says. “And he was reading Catch-22. It’s a very serious issue that allows for great humor.” It’s that mix of comedy and truly dark drama that makes Catch-22 stand out. But its success will boil down to one thing, as far as Clooney’s concerned. “It all rests on whether or not you root for a guy who’s a coward and who does a lot of crappy things,” Clooney says of Yossarian’s fight to escape the war. “I believe, because of Chris, you do.”

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