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Menswear issue 11/26/2013

At the Cannes Film Festival last May, Oscar Isaac was anxious. He had been to Cannes twice before—with the film Agora, in which he played Rachel Weisz’s suitor, and Robin Hood, in which he protected the honor of Léa Seydoux. In both cases, he had been told that the films and the festival would change his life, that he would be transformed into a major movie star. Isaac had half-listened; he wanted to believe the praise, but, over his career, he had learned not to have crazy expectations. Despite a twenty-minute standing ovation at Cannes in 2009, Agora, which takes place in ancient Greece, was deemed too esoteric for American audiences and received a very limited distribution—and Robin Hood just didn’t work. Isaac went home to New York and kept booking interesting parts. Guatemalan by birth and raised in Miami Beach, he has the rare ability to convincingly play different ethnicities, from Hispanic hustler to Russian mobster to English nobility. His versatility (he can also sing!) was a virtue and a complication: He was terrific in roles such as the doomed petty criminal in Drive and the security-guard savior in W.E., directed by Madonna, but he was not distinct enough for true cinematic stardom.

This story first appeared in the November 26, 2013 issue of WWD. Subscribe Today.

But Cannes in 2013 was different. Isaac attended the festival as the face of Inside Llewyn Davis, the new movie written and directed by Joel and Ethan Coen, in which he portrays a folk singer in 1961 who is equally talented and self-destructive. The character is the latest in a long line of beautiful losers created by the Coens, who consistently detail and embrace the unique and stubborn vein that runs through American culture with one gorgeously flawed protagonist after another, from Barton Fink to the Dude. Their latest antihero, Llewyn Davis, is a pure talent—he has no tolerance for the compromises that might help him become a commercial success, although he craves a large following. Based loosely on the life of singer Dave Van Ronk, who influenced Bob Dylan but never found mainstream success, Inside Llewyn Davis is both funny and a subtle meditation on what it is to be an artist.

After the first Cannes screening of the film, Isaac, dressed in a white button-down shirt and dark pants, walked into the press conference with the rest of the cast, the Coens, and T Bone Burnett, who supervised the music. Isaac had heard that the 10 a.m. screening had been a smash, but he was still nervous about the reactions of the international journalists. Immediately, a hand shot up and a critic from a London newspaper asked Isaac, “WHO ARE YOU? Where did you come from? And where are you going, because you are going to be famous!” Isaac laughed awkwardly but looked pleased.

“It was a great setup,” he told me four months later, over a 3 p.m. lunch on a cool fall day. We were in a booth at the Cafe Edison, in Times Square, an anachronistic spot that could have been a location for Inside Llewyn Davis. Isaac, who is 33, was wearing a thick gray sweater and jeans, and he had a military-like stubble on his head, which he had recently shaved. His dark, round, lemur-like eyes are his fortune: They are hugely expressive and can be, at once, menacing, melancholy, searching, love-struck. During Inside Llewyn Davis, he often looks simultaneously hurt and defiant—but at the press conference, he just looked shy and shocked. “I think I started babbling about artistic context,” Isaac continued, while eating a Greek salad. “It was intense at Cannes—a lot to take in. I found it very confusing.” 

Although he didn’t win best actor at the festival (that citation went to Bruce Dern, for his excellent work in Nebraska), Isaac’s career trajectory has definitely changed. He is in every scene of Inside Llewyn Davis, and he is riveting. “I understand Llewyn,” Isaac said. “This is a guy from a working-class background. He’s the worker—not the shooting star in the sky.” Strangely, Isaac is a mix of both: his twelve-year career has been a series of fast starts and sudden stops. As a teenager, he was in bands rather than plays, but he didn’t adopt a particular sound. “I was in ska bands, punk bands, hard-core rock bands. I was a musical whore, available to any genre,” he said. “I would sing acoustic ballads and industrial-sounding rock, but I wasn’t a good enough musician to do covers of other people’s songs, so I wrote my own. I was always trying to sound like something other than myself. At Juilliard, that changed.”

He and his buddies also shot elaborate home movies. “I would usually play the villain,” Isaac recalled, “and his henchman.” Interested in acting but unhappy with the drama teacher at his school, Isaac skipped over grade-school productions and instead auditioned for professional theater jobs in Miami. His mother and father, who is a doctor, were supportive, and almost instantly Isaac landed the part of a Cuban prostitute. “I can’t remember the name of the play,” Isaac said now. “But after that, I was asked to play a young Fidel Castro in When It’s Cocktail Time in Cuba, a play that was going to New York. Walking around Manhattan, I passed by the Juilliard School, and I went in and asked for an application. They told me that I had missed the deadline by a week. I took the application home anyway and came back the next day and said please, please, please, and the woman at the desk postdated my form. I auditioned a few weeks later, and I got in. That was the reason I moved to New York.”

On the application to Juilliard, Isaac was asked what life experiences would contribute to his acting. “I wrote that I had been a transporter in a hospital,” Isaac said. “For nearly two years, my job was to move people in extreme situations: take someone very ill to the X-ray machine, or take a dead body to the morgue. I saw people in the most extreme circumstances. Every day, that job made me think about existence. Even now, right before a take in a film, I’ll think, I’m going to die. I don’t say that to make myself sad, but to remind myself that nothing really matters. I’m going to die: It’s a liberating sentiment for me.”

At Juilliard, Isaac studied theater rather than film acting. “That school is like boot camp,” he explained, taking a sip of Coke. “They want to break you down and then build you back up into the actor they want you to be. I remember that one of the teachers said to me, ‘You have such a great sandy quality to your voice. Is that from all the flamenco you listened to growing up?’ I’m not going to comment on how racist that is, but no, I’m not from Spain, and I grew up listening to Jimi Hendrix rather than maracas.” He paused. “I worked hard at Juilliard, and because of the training there, I now have a skill set to do almost anything. For instance, in Llewyn Davis, I do a Queens accent. It’s a little thing that most people won’t notice, but I learned that kind of nuance at Juilliard.”

After graduating, in 2005, Isaac played a Russian criminal trying to sell plutonium in PU-239, a movie for HBO. “Years later, Madonna saw that film,” Isaac said. “She must have liked it, because she didn’t even ask me to audition for W.E. Instead, I was summoned to her lair. We talked: Madonna was very funny and very open about love and her personal life. I was struck by her candor, and I thought, Why wouldn’t I do her movie?”

W.E. was also a respite from playing bad guys: In the candy-colored, futuristic Sucker Punch, Isaac was the villain, the only human male in a sea of beautiful female comic-book warriors. (“It was a wild imagination explosion,” Isaac explained, “but it didn’t find an audience.”) I first noticed him in Drive, when he brought depth to a stock character: the wayward outlaw husband of an innocent woman. “I didn’t have to audition for Drive,” Isaac recalled. “I sat with the director, Nicolas Winding Refn, at the Noho Star for four hours and told him why I wasn’t going to do his movie. I think that made him like me. As it was written, I hated the character. In the script, he was a Mexican, tatted-up guy who beat his wife and gave alcohol to his infant son. When you saw this guy, you wanted the blond people—Carey Mulligan, who played my wife, and Ryan Gosling, who played my rival for her affections—to get together. I absolutely did not want to play that role. So Refn said, ‘Make him anything you want him to be.’ And I rewrote my character.”

Drive should have catapulted Isaac, but his complex portrayal of a man caught between his criminal past and his family was not seen by a large audience. “Around then, I auditioned for the lead in the Bourne sequel,” Isaac said, sounding a little frustrated. “I had twelve hour-long screen tests, and they kept calling me back and calling me back, but they eventually gave the part to Jeremy Renner, who was much better-known. The studio wasn’t willing to take a chance on me. It was upsetting. I was so worried that would happen again with Llewyn Davis.”

To cast their film, the Coens initially auditioned musicians rather than actors. After a short time, they realized that they needed an actor who could sing rather than a musician who could act. “I knew they had seen some musicians, and I was told to send in a tape with me singing any song,” Isaac explained. “I also knew that the script was loosely based on Dave Van Ronk’s life. I look nothing like Dave Van Ronk—he was a six-foot-five, 250-pound Swede that kind of resembled John Goodman. People would go see him because he was crazy. He howled. I tried to channel him by singing his song “Hang Me,” but I sang it very quietly. I filmed myself at home, and I did so many takes—maybe thirty. For me, it’s not so much talent alone as talent and obsessiveness.” The Coens watched the tape and then sent it to T Bone Burnett with a note that read, “What do you think of this guy? He’s a good actor, can sing, and isn’t square.” Burnett instantly wrote back, “I think we found our Hitler!”

A month passed before Joel Coen phoned Isaac to tell him that his life had almost definitely changed. “Joel called and said, ‘We’d like for you to be a part of our movie, if you want to be in it,’ ” Isaac recalled, still sounding surprised. “I assumed that it was the Bourne situation all over again—that the studio did not want to take a chance with me in the lead role, and Joel was giving me a smaller part. I said, ‘A part of it?’ Only then did Joel say, ‘We’d like you to play Llewyn Davis.’ ”

The Coens must have realized that Isaac understood the complicated nature of the character: Llewyn Davis is brilliant but impossible. The movie begins with him waking up on a borrowed couch in the Upper West Side apartment of a Columbia professor and his wife. As he leaves their apartment, he accidentally lets their large orange cat escape. Since Llewyn is instantly locked out of his temporary home, he must take the cat with him on his journey. “There were a few different cats,” Isaac explained, “and I have a complicated history with cats. I used to think I could speak to cats. As a kid, I would meow and cats would come to me, but not long ago, I met a cat that bit me. I felt his tooth go all the way into my arm. I ended up in the hospital for two days. I found out that a cat bite is a serious thing. So, four years later, I show up on the Coen brothers’ set, and they say, ‘These are the cats that will be tied to you by a wire.’ They attach the cat to you so it doesn’t run away. At one point, one of the cats freaked out and scratched my face. They just put makeup on me and sent me back to work.” He smiled. “That’s my job.”

The sight of Isaac/Davis balancing his guitar case and a tabby cat is the key image of the film. It is also consistent with the cinematic vision of the Coens. All of their characters (Llewyn Davis especially) are like cats: prickly, idiosyncratic, independent, fascinating. Cats never try to be likable, but are always true to their nature.

“You can’t really train a cat,” Isaac said, as he was getting ready to leave. He was late for a rehearsal for an Inside Llewyn Davis folk concert at Town Hall. He would be performing songs from the film, and he was jittery about singing alongside full-time musicians such as Marcus Mumford, the Punch Brothers, and Elvis Costello. “I heard that both Joan Baez and Patti Smith are going to perform,” Isaac said. “That’s intimidating. I can’t decide whether to sing the songs as Llewyn or myself. At this point, it’s getting hard to tell the difference.”