Daniel David Stewart Embodies Avarice in 'Catch-22'

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How do you play a metaphor? Daniel David Stewart will tell you it isn’t easy. As Milo Minderbinder, the war profiteer extraordinaire in the new Hulu series Catch-22, he portrays the embodiment of American capitalism run rampant, a mess officer whose black-market trading network reaches across Europe and beyond during World War II, heedless of any allegiance except to the dollar. Milo is just a part of the satirical tapestry of the series, based on Joseph Heller’s iconic novel exposing the absurdity, hypocrisy, and brutality of war, but in taking aim at one of our country’s foundational tenets, he is perhaps the most scathing. He is a stand-in not just for those who seek to turn a profit from the disorder of a continent torn apart by conflict, but for anyone who sees commerce as a competition divided cleanly into winners and losers. “He’s such a salesman,” Stewart says, “trying to constantly casually bully people into wanting the things that he wants for his own profit.”

Like the novel on which it is based, Catch-22 centers on John Yossarian, here played by Christopher Abbott, an American bombardier who finds himself sentenced to an ever-increasing quota of flight missions and is slowly ground down by the bureaucracy of war. George Clooney serves as executive producer and plays General Scheisskopf, an officer obsessed with synchronized parades, and Kyle Chandler is Colonel Cathcart, who seems to be equal parts sadism and incompetence. Shot in burnished golden tones on the sun-drenched Mediterranean island of Sardinia, the show is strikingly gorgeous but also painfully tragic, what Stewart calls a “beautiful, strange mood piece.” Yossarian’s friends are killed one after another, war crimes are ignored, and the folly of man comes across as both comical and devastating, sometimes in the same scene. “It’s such a delicate balance,” Stewart adds. “You want to show the absurdity of war and how insane it all is, but at the same time, if you lean too far into that, then when these deaths happen or when all this crazy stuff goes down, that’s not going to have the weight that it needs. That was, I think, the most difficult challenge.”

In dealing with olive oil and oranges rather than bullets and bombs, Milo does not traffic in bloodshed like those who fly into battle every few days, but his influence is perhaps even more insidious. One episode is largely devoted to exploring the scope of his Syndicate—he is elected the mayor of Palermo before enlisting Yossarian to impersonate Nelson D. Rockefeller to seal a deal in Oran—while he demonstrates himself to blissfully unaware of his own amorality as he recommissions German planes for shipping cargo and puts local Italian children to work. Hulu’s Milo is notably less severe than Heller’s, played with a gently needling charm that will be familiar to anyone who has encountered the soft persuasion of a used-car salesman. Stewart admits that he nearly begged to audition for the role, going so far as to cut his hair and find a vintage uniform to match that of Jon Voight’s Milo in the 1970 film.

His interpretation was met with some hesitation from the creative team at first. “I think they had an idea of who the character was and I had a very clear idea of who I thought the character was and they weren’t completely convinced,” he recalls. “Then luckily George Clooney happened to see my tape and was like, ‘That’s our guy.’” He worked to strip away some of Milo’s specificity—a Brooklyn accent was vetoed—to turn him into more of the universal symbol he is meant to be, a decision he calls somewhat instinctual and that required some firm self-assurance. “It was the first time I had ever fully just followed my gut in every step of the way,” he says. “When everyone was like, ‘Oh you shouldn’t do this,’ or ‘That’s going off,’ I was just like, ‘No, this is what I feel so I’m going to do it.’ It just kept seeming to lead me in the right direction.”

First published in 1961, Catch-22 is a Cold War-era novel about World War II informed by Heller’s opinions about the Korean War, but its themes continue to be pertinent in our age of uneasy peace. “It’s about powerful men abusing their power for advancement,” Stewart argues. “It’s always relevant because we’re constantly surrounded by the foibles and the ridiculousness of these older, mostly white men who are in power and not necessarily looking out for the people below them, but looking at their own advancement.” As a warning against avarice, in fact, Milo can seem particularly pertinent. “I felt such a responsibility with Milo because he represents so much of what America is,” Stewart continues, “specifically this capitalist idea of, ‘If it fits into my bottom line, it’s okay, let’s all abuse this system together.’ The entire fabric of what makes up America is this toxic capitalist mindset.”

A veteran of the stage, Stewart jokes that the biggest lesson he learned from Catch-22 was how to curb his need for validation without the “instant gratification” of the audience’s reactions. “You’re never going to get that on a film or television set, as you rightfully shouldn’t,” he laughs. “It’s a human need to go, ‘Let me know I’m doing the work well,’ or whatever, but no, you have to just show up and do your job.” Raised by two parents who met performing in musicals in college and later ran a dinner theater, Stewart says he started performing “before I was born.” A teenage trip to New York specifically to see plays like the Pulitzer winner August: Osage County and director David Cromer’s celebrated stripped-down take on the classic Our Town helped cement his goals. “I was physically moved and saw the world in a different light than before,” he recalls. “When we’re at our luckiest, performers can really give something to the public, whether that be making someone laugh or giving them a new outlook on life. So few people get an opportunity to change people’s hearts and minds through their work, so if you can have that, that’s a dream come true.”

After a few years working in local productions in his native Southern California, Stewart made his Broadway début in Deaf West Theatre’s 2015 revival of Duncan Sheik and Steven Sater’s epochal musical Spring Awakening in a cast composed of both deaf and hearing performers. He played the voice of Ernst, a shy teenager slowly discovering his love for another boy, alongside Joshua Castille, who performed the role in American Sign Language. He also played the piano, an instrument he had never properly studied. “I knew three songs on the piano maybe, but I went in the audition and played one and they told me, ‘Oh we’d probably only have you play a couple songs and have people rotate,’” he laughs. “Then the first day of rehearsal I showed up and they put the whole score in front of me and were like, ‘Memorize this!’ and I was like, ‘Ok you don’t know what you just did.’ There was no part of me that ever thought I’d be playing an entire piano score on Broadway.’”

He returned to Broadway in 2018 for a brief run in The Band’s Visit, the Tony-winning musical about an Egyptian police orchestra’s accidental trip to a remote town in the Israeli desert, stepping in for an actor who became ill. Having originated the role of Papi Off Broadway before being replaced for the Broadway transfer, Stewart admits to having had “many mixed emotions” about the decision, especially coming as it did after a few difficult months. “I’d done a pilot and I had auditioned for a new show and I remember getting on a flight from LA to New York and I was like, ‘Ok by the time I land in New York I’m either going to have two jobs, one job, or none,’” he recalls. “I landed in New York and none of them happened. I was like, ‘Whoa okay,’ so I put my tail between my legs and went off. I’d gotten to the end of 2017 and I was completely broke and working at my hometown mall during Christmastime at a kiosk, running into old high school friends who were like, ‘I thought you were in New York doing Broadway!’ And I was like, ‘Well, I’m selling you a portrait of Prince for twenty-five dollars, here you go.’”

Still, Stewart says he is thankful things worked out the way they did, as that fallow period was in some ways necessary to make his new prominence possible. “If The Band’s Visit had happened on Broadway for me, I wouldn’t have even been able to audition for Catch-22, so everything happens for a reason,” he says. “I had gotten a lot of nos back to back to back for half a year and I had no money and I was thinking if I had to move back in with my parents and what my survival job was going to be. I think that all bolstered me when I was auditioning for Catch-22 to be like, ‘I have nothing to lose, so I’ll just follow my gut and damn the consequences.’ All those nos happened for the right yes to come along.”

Catch-22 is now streaming on Hulu.