James Caan Was Unlike Any Other Leading Man

James Caan rarely reminisced. “I usually talk about how much fucking money I lost on football games,” he told me in February 2021. His time as a Hollywood star? “I don’t really think about it too much—unless I get guys like you fucking bothering me.”

This assertion came at the end of a spirited conversation about preparing to play a safecracker in Thief, a cult classic that perfectly captured his charming tough-guy energy. Forty years after appearing in Michael Mann’s neo-noir, Caan sounded like he could still bust open a bank vault. He even spent a few minutes explaining why the inside of a heavy-duty safe is layered with copper. “It binds the drill,” he said. “So as you got deeper, you had to just kind of give it and take it, give it and take it, just like you were fixing a little bitty cavity.”

For all of his posturing, Caan clearly loved his job. What he hated was the pretentiousness that came with being a leading man. After his Academy Award–nominated performance as Sonny Corleone in The Godfather, he knew that he’d never fully escape it. But Caan, who died at age 82 this week, still did his damndest to bend his career to his will. Over and over he turned down splashy roles in classics and blockbusters in favor of riskier parts.

When Francis Ford Coppola told him about Apocalypse Now, Caan immediately balked. “All I heard him say,” he once told The Washington Post, “was 16 weeks in the Philippine jungle.” He also had no use for sequels—they bored him. “Everybody wants to do Rocky 9 and Airport 96 and Jaws 7,” he once said. “And you look and you listen, and what little idealism you have left slowly dwindles.”

Famously, Caan agreed to play the bedridden romance novelist Paul Sheldon opposite Kathy Bates’s deranged Annie Wilkes in the Stephen King adaptation Misery only after a long list of stars refused. “That’s what made Brando so great,” Caan told me. “You were more interested in him because he was unpredictable. And that’s what I think the key word is: unpredictable.”

Caan, a shit-stirring Jewish guy from Sunnyside, Queens, gravitated toward films that embraced and commented on his surly persona. Many of his most iconic characters—Axel Freed in The Gambler, Jonathan E. in Rollerball, Frank in Thief—were both combustible and vulnerable. And while he may have been a classically trained actor who specialized in playing complicated men, he consistently called out the self-seriousness of his profession. “I used to think a lot of these actors just go a little too far,” he told me. “They lose 90 pounds [for a part]. What the fuck is the matter with you?”

Still, Caan was not afraid to occasionally lose himself in a role. Take, for example, Thief. Mann wanted Caan to become Frank. “What does he think? What does he do? What does he dress like? Where did he keep his tools?” Mann said in 2021. “What are his movements during the day? What are the happenings of his life? The real specifics.” So Caan learned how to crack safes. He hung out with real thieves. He trained at Gunsite Academy, an Arizona firearms school founded by Jeff Cooper. Mann said that Caan, a former football player and rodeo team roper, was a natural. But, unsurprisingly, he bristled at the instructor’s methods.

“Jeff Cooper took himself very, very seriously and that wasn’t going to fly,” Mann told me in 2021. “It was raining and Jimmy and I are getting wet. So Jimmy says, ‘It’s time to go in,’ and the guy says, ‘Well, we’ll take a 10-minute heat break and reassemble on the parade ground.’ Jimmy looks at me, I look at him, and Jimmy says, ‘Where’s the parade ground?’ [Cooper] says, ‘Over there.’ Jimmy says, ‘It’s a fucking parking lot.’”

Caan “was very funny,” Mann said.

One of the actor’s most well-known roles may have been an NFL player dying of cancer in the ultra-earnest 1971 TV movie Brian’s Song, but Caan had comedic chops. He pops up as a criminal in Wes Anderson’s Bottle Rocket. He plays a toupee-wearing drug lord in the Adam Sandler–Damon Wayans vehicle Bulletproof. And he steals his scenes as Will Ferrell’s long-lost father in Elf.

Late in his career, Caan appeared in dozens of mainstream Hollywood movies, some of which were more successful than others. Nineties kids probably remember him as the coach in the college football drama The Program and as Arnold Schwarzenegger’s nemesis in Eraser. But looking back at his time as an actor, Caan expressed fondness for his smaller films. When the “people who you really love and really respect, when they like it, then jeez, you’ve done it,” he said. Thief made only about $11.5 million at the box office. But the role of Frank, he added, “is surely one of my favorites, if not my favorite.”

“Tell him hello,” Caan said of Mann when I told him I was scheduled to interview the director next. “And tell him I need a fucking picture before I get too old.”

With the help of Twitter, Caan spent the last few years having more fun reminiscing than he ever had before. The medium turned out to be perfect for the wise-ass octogenarian. On his account, which piled up more than 120,000 followers, he posted photos from the sets of his movies and cutting one-liners—closing every single message with the same declarative phrase: End of Tweet.

A few weeks after I wrote an ode to Caan’s tweets as part of The Ringer’s list of “Things We Actually Loved Watching in 2020,” I received an email from his assistant asking for my address. Soon a package arrived at my apartment. Inside was a baseball cap emblazoned with three words: End of Tweet.

Looking at it now, it’s the perfect way to remember Caan’s voice: macho, hilariously to the point, and unmistakably his.