Cinematic tough guys often subvert their image by appearing in comedies. (Think of Arnold Schwarzenegger in Kindergarten Cop or Clint Eastwood hanging out with an orangutan.) Their onscreen persona is so intimidating that occasionally going for the funny can be a winning strategy: For a change, we see their badass characters made the butt of the joke. It’s a surprising but also shrewd pivot, allowing these seemingly bulletproof actors to suddenly feel more relatable.
The late, great James Caan was a master at portraying hard-edged, ultra-masculine characters in everything from The Godfather to Thief. In real life, he didn’t suffer fools, was married four times and battled drug addiction. He hails from a bygone era of guy’s guys actors who you wouldn’t want to cross. This, of course, made him a natural for comedy.
Many of the appreciations out today mourning his passing are, deservedly, focusing on his dramatic work, but it’s worth spending a moment admiring the funnier films he tackled later in his career. In particular, Misery, Bottle Rocket and Elf, which showcased Caan’s comedic strengths. He may not have always been on the same wavelength as his directors, but the results (and the laughs) speak for themselves.
Released in 1990, Misery was adapted from a Stephen King novel, telling the story of a novelist, Paul (Caan), who gets into a terrible car accident, is rescued by his biggest fan, Annie (Kathy Bates, who won an Oscar for the role), and must then write a new book that makes her happy — or else. Although a horror/thriller, the film was also darkly comic, with Bates and Caan deftly playing off each other, poor bedridden Paul at her mercy.
“I sometimes wondered if this was a sadistic joke on [director Rob Reiner’s] part,” Caan said at the time. “You know, ‘Let’s get the most hyper guy in Hollywood to stay in bed for 15 weeks.’” Misery found the absurdity in the situation, riffing on toxic fandom long before #ReleaseTheSnyderCut, but what was also funny was that it was Caan in the role. For an actor who long flaunted his machismo, portraying a character who’s trapped by a female fan who had total control over him was also a sly flip of gender power dynamics. The more unstable Annie got, the more terrified and indignant Paul got — in this blackhearted comedy, Caan was the straight man, but also the flat-on-his-back man, a dude stripped of his masculinity by a woman who just wants him to write more cheesy romance novels.
Misery helped kickstart a comeback for an actor who’d been Oscar-nominated for The Godfather and gone on to do strong work throughout the 1970s and early 1980s, before watching his career stall. After Misery, he alternated between roles as criminals and cops, usually in dramas and thrillers but also sometimes in comedies. Too often, these funny films weren’t so funny — Mickey Blue Eyes is best forgotten — but in 1996’s Bottle Rocket, he found just the right slant on Mr. Henry, a small-time crook who intimidates the even-smaller-time crooks who are the film’s lovable antiheroes (Owen Wilson, Luke Wilson, Robert Musgrave). Reportedly, Caan had recently gotten out of rehab when he signed up for Wes Anderson’s feature debut, not entirely understanding the filmmaker’s peculiar sensibility.
“One thing I began to realize when we started doing that movie is that Owen and Luke and Bob Musgrave and I, we had our own way of working together,” Anderson said in 2008. “We’d been doing our own experiments, and I’d been making my own shorts, and as we started making Bottle Rocket with other people, I began to realize, ‘I think the way we’re doing things is not quite right, because some of our techniques seem to be getting sort of a puzzled reaction.’” In fact, Anderson recalled that, at one point during filming, Caan turned to him and said, “This isn’t supposed to be a comedy, is it?”
Still, the director insisted, “I think he was amused by it. He wasn’t there for long, and we had fun with him, and he seemed to be getting a laugh out of it all.” And you can see Caan relaxing into his position as the seasoned pro on a set filled with hungry, inexperienced young filmmakers and actors. Not unlike how Anderson would give veteran actors Bill Murray and Gene Hackman strong, autumnal roles in his subsequent films, Bottle Rocket was a crime caper that had a huge amount of reverence for its august star, and in turn Caan lent the film a relaxed gracefulness that grounded the movie. He felt like a real person, albeit a slightly bizarre one — seriously, what’s up with his fascination with martial arts? — in a gently quirky, off-kilter reality. Caan was funny by not even trying.
In the early 2000s, Caan landed one of his steadiest gigs, that as the lead in the long-running NBC series Las Vegas, smoothly transitioning to elder-statesman status. But he was far more memorable in a film that came out the same time, Elf, playing Walter, a grouch who runs a children’s book publishing company, unaware that he has a son named Buddy who’s been living as an elf at the North Pole for decades. This was the movie that made director Jon Favreau and comic Will Ferrell big shots in Hollywood, and Caan’s slowburn annoyance was a perfect counterpoint to Buddy’s wide-eyed optimism and unhinged glee. The more flummoxed Walter got about Buddy, the more hilarious the scenes got, while also setting the stage for Caan to deliver what’s ultimately one of his warmest performances as an unwitting dad who becomes a better person.
“Will and I were kind of starstruck by him,” Favreau would say later. “But Will would bust his balls a lot, which was fun, too. Will gave him, as a wrap gift — he wrote a note that said, ‘Great working with you. The first one is a little bit slow, but the second two are really good.’ And it was The Godfather trilogy.”
Read about the making of Caan’s comedies, and what comes through clearest is that he may not have been the most naturally gifted comedian. Which isn’t to say he’s not funny in something like The Godfather, but he didn’t necessarily gravitate to making lighthearted films, a fact that worked to those movies’ advantage, utilizing his characters’ discomfort for laughs.
“The thing with Caan is, he’s got a great sense of humor,” Favreau went on to say. “So if you could make him laugh, all the tension disappears. We kept him laughing, and he kept us laughing. It took him a while to get with the programming. I surrounded him with a lot of improvisers, like Andy Richter and Kyle Gass and Amy Sedaris. When I’m working with improv people, I give them the green light to just bring it and try things. So every take was different. Eventually, something just clicked in Jimmy and he just went with it. He was a lot of fun.”
Even so, James Caan knew what film would be his legacy. In that same interview, Favreau recalled going out with the veteran actor to dinner. “Whenever we’d go into an Italian restaurant, they’d put on The Godfather soundtrack,” said Favreau. “Everywhere he goes, The Godfather theme.” Considering that Caan was Jewish, not Italian, hopefully he found that funny. After all, in his best comedies, he always mined the humor of being put in awkward situations.