"James Caan in The Godfather"

James Caan often described himself as "the only New York Jewish cowboy." He was rugged and intense, portraying iconic hot-heads like Sonny Corleone from "The Godfather" with volatile bursts of rage, but there was more, too. In 1981, Michael Mann got Caan to go deeper with "Thief." Caan had that thing great performers have: He could stop talking and you still wanted to know what he was thinking. As one of Hollywood’s most iconic tough guys, he often didn’t have to say anything at all.

The Bronx-born, Queens-raised Caan didn’t drop the regional accent. It was his calling card and let you know where he stood. When directors needed a "heavy," Caan was the man. Well into his 70s, the actor was landing intimidating parts. Yet, he was also happy to play on his well-worn persona for laughs, too, as he did for a whole new generation opposite Will Ferrel in Jon Favreau’s classic 2003 ode to the Christmas spirit, "Elf."

Caan died in 2022 at the age of 82, leaving behind an indelible body of work stretching back a stunning seven decades. His first role was in a black and white TV series "Naked City" in 1961. His final film, "Fast Charlie," has a 2023 release date. It’s fitting that his fans will get new stuff from this man even after he’s gone. His body of work is immortal.

15. Rollerball

James Caan in "Rollerball"

To understand how Hollywood could think rollerskating (not even blading mind you) could plausibly be the sport of the future, you’d have to recall how popular disco-ball lit rinks were in 1975.

This movie doesn’t hold up, but I swear, it was interesting at one point. James Caan stars as Jonathon E. He’s the big rollerball star in this dystopian future, set in the year — wait for it — 2018! Corporations have replaced governments and different regions compete in this violent game that’s sort of a combination of roller derby and jai alai. "Rollerball" is similar to Arnold Schwarzenegger’s "Running Man" or even "The Hunger Games," in that one hero defies an exploitative, entertainment-oriented corporatist system.

Years later (with no rollerball craze in sight), this movie comes off as unintentionally funny. Dudes skating in circles wearing those vintage ’70s-era football helmets is just comedic. As always, Caan commits and carries the film because he was relentlessly great.

14. Dogville

James Caan in "Dogville"

James Caan did blockbusters, adult dramas, kids’ movies, and far-out arthouse indies, too. The oddest of that latter group is definitely "Dogville" from 2003, and it’s not for everyone.

Nicole Kidman stars in this curiosity from weirdo auteur Lars Von Trier, who more recently horrified audiences with his gruesome ode to serial killer movies with "The House That Jack Built" in 2018. "Dogville" is hardly any less subtle than that gore-fest, but takes more patience. The entire film is shot on a sparsely decorated sound stage that the director makes no effort to conceal. Right away, you know you’re in the realm of some kind of Brechtian theatre experiment.

Set during the Great Depression, the film features Kidman as Grace, who is on the lamb in the small town of Dogville, hiding from gangsters in hot pursuit. The insular and cultish locals offer to take her in but only so long as she works tirelessly to please them. Her servitude quickly takes on a far more sinister and torturous tone. Dogville is clearly meant to be America in miniature. James Caan plays a kind of avenging angel to this hellscape vision of the United States as "the big man." His full identity is a twist I won’t spoil, but suffice to say "Dogville" turns into a revenge film and Caan really brings it home with a bang.

13. Dick Tracy

James Caan in Dick Tracy

"Dick Tracy" was disappointing relative to expectations in 1990, but that only means we can now declare it an underrated cult classic. This ambitious adaptation of the 1930s-era hard-boiled detective comic strip had a budget of nearly $50 million and was packed with massive movie stars like Warren Beatty, Madonna, and Al Pacino — all to bring to the surreal world of the titular yellow duster-clad flatfoot to life.

James Caan has a somewhat minor role in this massive ensemble full of legends in cartoonish prosthetics. He plays Spaldoni, one of the many warring gangsters inhabiting the hyper-colored art-deco underworld. Tracy wants to bust Pacino’s gangland head honcho, Big Boy, and to do that he gets entangled with Madonna’s stylish take on a femme fatale.

In retrospect, the great thing about "Dick Tracy" is that its bold aesthetic now feels like a template for modern graphic novel adaptations like "Sin City" or even "The Watchmen." Alongside Tim Burton’s fanciful "Batman" in 1989, these were the first two films to go for that over-the-top comic book noir aesthetic. All the "Dick Tracy" sets are practical, and the whole movie is awash in only four colors borrowed from Chester Gould’s comic strip that was originally printed exclusively in red, green, purple, and yellow, to save money at the presses.

12. The Yards

James Caan in "The Yards"

James Caan’s career was so long that a lot of moviegoers only knew him from films like "The Yards" in which he played one kind of elder criminal patriarch or another. No doubt, part of his longevity was in that he was so good at playing bad, and in "The Yards," he does it with rueful regret.

A young Mark Wahlberg stars as Leo Handler, an ex-con freshly paroled and trying to get back on his feet. He takes a job at the train yards run by Caan’s mustachioed and suspiciously connected union boss, uncle Frank Olchin. Frank warns Leo to steer clear and get a straight job, but he needs the money and teams up with his cousin’s enforcer boyfriend (Joaquin Phoenix). Soon, he learns there’s no such thing as easy money.

Director James Gray of "Ad Astra" fame basically remade this movie in 2007, again starring Wahlberg and Phoenix, with "We Own The Night." That’s good too, and better known, but it doesn’t have James Caan, so "The Yards" is definitely the better of the director’s similarly cast thrillers.

11. Bottle Rocket

Robert Musgrave, James Caan

"Bottle Rocket" from 1996 is Wes Anderson’s least "Wes Anderson" film, mostly because it’s his debut. It has the director’s signature light-hearted caper plot, but none of the expensive and elaborately symmetrical set design.

Back in the late ’90s, hot indie talents sometimes attracted one established star, and James Caan plays that role here. The plot is kind of like "Reservoir Dogs" meets "Idiocracy." Owen Wilson plays dopey crook, Dignan. He rescues Anthony (Luke Wilson) from a psych ward, and the two hatch a "75-year plan" for a series of heists. Anderson’s sets might not be actualized at this date, but his whimsy is all there as these two buffoons begin their life of crime in Texas by targeting Anthony’s mother’s house for a "practice heist."

"Bottle Rocket" has always had a devoted cult following, and even with its modest $5 million budget, it’s arguably better than Anderson’s "The Life Aquatic," which cost ten times as much. Caan’s part is small yet memorable with the actor inhabiting the role Bill Murray usually occupies in Anderson’s films. He plays a warm father figure, Mr. Henry, the big boss to this band of incompetent crooks. Caan generously lent his legitimacy to this movie that looks like a student film and helped launch the careers of three of the biggest Hollywood names in the decades that followed.

10. The Rain People

James Caan in "The Rain People"

If it seems like James Caan had the cut of an athlete, he did. He played quarterback at Michigan State for a season in 1956. Caan joked he was used as a tackling dummy, and according to The Los Angeles Times, he didn’t see the field much. With a wiry frame well below six feet, the actor was tiny by college football standards, so just making the team was impressive. Competing at his relatively ordinary size would’ve given him some special insight into the violence of this glorious game.

The hardscrabble experience came in handy for Francis Ford Coppola’s sentimental 1969 road movie, "The Rain People." Caan plays Jimmy "Killer" Kilgannon, a former football star with a serious brain injury sustained on the field. He’s picked up by a pregnant young woman Natalie (Shirley Knight) who has just walked out on her husband. She’s on a spontaneous journey of self-discovery and wants to help Jimmy navigate the world. The two form a tense but touching relationship, but their rollercoaster ends when they come across an abusive cop (Robert Duvall) who wants Natalie for himself. Jimmy will remind you a little of Lenny from "Of Mice and Men," and this early melodrama from Caan’s most iconic collaborator has a similar sense of sadness.

9. Cloudy With A Chance Of Meatballs

James Caan in "Cloudy With a Chance of Meatballs"

When James Caan got into TV and movies, the Westerns of the 1960s often did not record live sound on the set. Everything was dubbed later in post, so the man was a natural for the computer-animated feature "Cloudy With A Chance Of Meatballs" in 2009.

This fantasy comedy has all the whimsical charm you want. Economic depression has come to Shallow Falls and the people are eating nothing but sardines. Gross! That’s when inventor Flint Lockwood (Bill Hader) builds a machine that makes it rain meatballs. But when it rains, it pours, and soon the town is facing a real flood of foodstuffs.

Caan plays the inventor’s towering father, Tim Lockwood. He’s a hulking, old-fashioned man with a bushy stache who wants his son to get his head out of the clouds. Caan’s voice is almost unrecognizable as he leans into a much slower version of his familiar New York accent. The best scene is when this literal-minded, blue-collar boomer tries to navigate the "windows" of a desktop computer. This is a family-friendly gem and Caan, nearing the end of his incredible career, was still hitting high notes.

8. A Bridge Too Far

James Caan in "A Bridge Too Far"

At nearly three hours, "A Bridge Too Far" from 1977 might be a smidge too long, but this ensemble World War II action-drama captures some indelible scenes of just how terrifying the urban warfare of the European Theater was.

The huge cast is led by Sean Connery, Michael Cane, Laurence Olivier, and Gene Hackman, but James Caan has a memorable role as a sergeant who forces a U.S. combat surgeon to triage his badly injured friend at gunpoint. It’s a moving moment in which the indifference a surgeon needs to psychologically survive a total war suddenly smashes against the will of the individual.

The plot follows the real Operation Market Garden in 1944 in which 35,000 troops were air dropped far behind enemy lines in the Nazi-occupied Netherlands. This Richard Attenborough-directed film is somewhat unique in the genre for depicting a failed Allied mission, but a doomed cause is always tragically compelling. Caan is excellent as usual in this gritty war movie that transports you into the stone and rubble reality of the house-to-house fighting that saved the world.

7. Brian’s Song

James Caan in "Brian's Song"

"Movie of the week" became a pejorative term for the generally slipshod production values of network TV film events of the 20th century. "Brian’s Song" from 1971 isn’t exactly cinematic, but James Caan elevates this otherwise sentimental portrayal of the 1960’s era Chicago Bears halfback Brian Piccolo who died at 26 of a rare and aggressive type of testicular cancer.

That’s the song part, a ballad really, but the film is also a feel-good, civil rights-era story about the friendship between the modestly talented Piccolo and legendary Bears running back Gale Sayers (Billy Dee Williams). Sayers was Black, but the two men become roommates and inseparable on and off the field in an era of NFL football when some segregation was still part of the game. The bond between these tough guys is touching and tragic. It’s a real tear-jerker. Once again Caan works his rugged magic to convincingly portray a football star with a devastating vulnerability.

6. The Gambler

James Caan in "The Gambler"

"Hit me" is how you ask for another card in 21, and that suits the endless masochism of James Caan’s table game addict in "The Gambler" from 1974.

Caan plays well-heeled college literature professor Axel Freed. Even though he’s the scion of a wealthy New York furniture magnate and teaches the 2+2=5 relativism of Fyodor Dostoevsky novels by day, he compulsively loses far more objective sums to the mob by night. As the leg-breaking enforcers start circling, Axel anxiously approaches his mother for help with the cash, all while dragging along his long-suffering girlfriend Billie (Lauren Hutton). At first, Caan plays it all with the matter-of-fact cool of a man for whom things have always just worked out. However, his enablers are only getting him in deeper.

Caan’s increasingly cornered Mr. Freed has an intensity that captures the compulsive spirit of a man who only feels alive with dice in the air. Mark Wahlberg starred in an unnecessary 2014 remake of this film, but the better successor is the disquieting claustrophobia of 2019’s "Uncut Gems." Adam Sandler and the Safdie brothers arguably have the better film about this specific addiction, but Caan cut the mold for the kind of self-destructive soul who will never know when to fold them.

5. El Dorado

James Caan "El Dorado"

It’s a little sad that the saloon-door swinging Western genre so popular in the 1960s is all but dead. It is, however, remarkable how James Caan’s career spanned the heyday of John Wayne to the supremacy of the Marvel movie.

Howard Hawks’ "El Dorado" from 1966 is really the movie that made Caan a star. He was a TV actor before he landed this supporting role billed below both Wayne and the equally legendary Robert Mitchum.

Mitchum plays the drunken sheriff of El Dorado, J.P Harrah, who enlists the help of a gunfighter Cole Thorton (Wayne) to fend off incursions by a greedy tycoon (Ed Asner). Clint Eastwood’s "Pale Rider" has basically the same plot — so do "Quigley Down Under" and many others. The virtuous gun-fighter saving settlers is a staple of the genre. Caan is only about 26 in this film and in the full bloom of his glorious youth. He really stands out as Wayne’s knife-wielding sidekick in this absolute essential of all three actor’s astounding careers.

4. Misery

James Caan in Misery

The best adaptations of Stephen King’s books are consistently his stories like "Stand by Me," "The Shawshank Redemption," and of course "Misery," which don’t have the horror author’s signature supernatural elements.

Make of that what you will. I’d say it’s because deus ex machina plots work better in your imagination. Regardless, this is a straight-up thriller and Caan is brilliant as a stand-in for King himself. He’s novelist, Paul Sheldon, who gets in a serious car crash and is rescued by a seemingly doting ex-nurse Annie Wilkes (Kathy Bates). She soon turns out to be a deranged and obsessive fan who holds him captive, forcing him on pain of torture to reverse the death of one of her favorite characters. The whole thing has the feel of King grappling with angry fan mail and then sitting down to pen the ultimate comeback to the well-read Karens in his inbox.

"Misery" is an absolute classic, and part of the appeal is definitely in the casting of Caan in the most physically vulnerable role of his career. Not only is he badly disabled as he tries to escape Annie’s clutches, but he’s also something of an artist type. Bates deservedly won an Oscar in 1991 for her frighteningly unhinged performance, but it’s Caan who steps outside of his wheelhouse as he makes you feel his extraordinary pain.

3. Elf

James Caan in Elf

Let me put aside my personal preference for more Jimmy Stewart-oriented Christmas classics and just give a big hug to this story of Buddy the oversized elf (Will Ferrell), who leaves the North Pole and meets his real father, Walter, played by James Caan at his crotchety best.

Caan is the film’s Grinch or Ebenezer Scrooge. He’s a New York businessman and doesn’t have the patience for this apparently deranged man in an elf suit he assumes must have wandered away from either Macy’s Christmas display or an insane asylum.

Happy to shed his tough-guy persona to be the straight man and let others shine, Caan played a lot of roles like this in his later career. Sure, he was famously intense, but Ferrell’s performance cracked him up on the set, according to a DVD commentary track by Favreau. You can actually catch him break just slightly in his scene where he takes Buddy to the doctor for a DNA test. Getting to see one of Hollywood’s hardest men crack, even a little, feels like a Christmas miracle.

2. Thief

James Caan in "Thief"

"Thief" might have been James Caan’s favorite James Caan movie — and for good reason. Caan was coming off "The Godfather" and had serious heat. "At the time I was a big shot, and whatever I wanted to do, they did," he recalled to Bright Lights.

What he chose was this stylish neo-noir heist film, and it was an unlikely pick. Nobody knew back in 1981 that first-time feature director Michael Mann was a genius. Mann, of course, would go on to make the greatest heist film of all time with "Heat." "Thief" is a lot like a prototype for that masterpiece. Caan described Mann’s infamous intensity on set as only he could: "And Michael — this little Napoleonic workaholic. This guy was nuts. But I liked it. That film, and that character, it’s one of my fondest memories."

"Thief" kicked off the neon-noir genre later copied to such great effect by stylishly lit films like "Drive." Caan plays a highly skilled jewel thief who makes the mistake of going full-time for his double-crossing fence, Leo (Robert Prosky). As the two men go to war, everything Caan’s ex-con has carefully built in his cautious criminal career goes up in flames. This might be the actor’s best performance as he brings serious range to the backstory of this hardened man whose life of crime is the result of a brutal past.

1. The Godfather

James Caan in The Godfather

"The Godfather" cemented James Caan’s legacy, but the Bronx-born star was already famous and brimming with confidence. He didn’t even feel he needed a screen test for the role of Sonny Corleone. "Test what? You got a Porsche you want me to drive around the block?" Caan reminisced to Variety as only he could.

Caan also recalled director Francis Ford Coppola initially had him pegged to play the Al Pacino part as Michael Corleone. However, the actor wanted the role of the angry eldest son in Mario Puzo’s Mafia epic, and he got his wish.

Caan’s searing Sonny balances the pathos and the volatility of this family. He’s the contrast to Pacino’s Machiavellian Michael, who ultimately takes over the family business from the similarly shrewd Vito Corleone (Marlon Brando). Caan improvised the scene in which he beats down the wife-abusing and treacherous Carlo (​​Gianni Russo). That sets up his gory death, and there was no other way for a loose cannon like Sonny to go out. Caan recalled Sonny’s famous finale was dangerous too. "It was very scary," he explained. "I had 147 squibs on me and there were 5,000 in the tollbooth and the truth is that I only did it because there were girls on the set. I remember [special effects head] A.D. Flowers putting these wires on me … mumbling to himself about how he never put this many squibs on somebody in his life … Thankfully we only did it once."