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The Best James Caan Movies And How To Watch Them

James Caan talking in the study in The Godfather.
(Image credit: Paramount)

James Caan, the Academy Award-nominated actor best remembered for his roles in classics like The Godfather, Thief, Misery, and Brian’s Song, passed away on July 8, 2022, leaving behind a body of work and legacy that is mostly unmatched by both his contemporaries and those who followed in his footsteps. Immediately following the screen legend’s passing, many of his co-stars, other Hollywood figures, and fans shared tributes to the late star, praising his accomplishments both on and off the screen.

Another way to pay tribute to one of the greatest actors of all time, I have put together a list of 13 of James Caan’s best movies that show why the electric, dynamic, and versatile actor was and remains such a legend.

James Caan in The Godfather

(Image credit: Columbia Pictures)

The Godfather (1972)

Regarded as one of the best movies of all time, Francis Ford Coppola’s 1972 epic, The Godfather, follows the Corleone crime family over the course of several decades, first with a focus on family patriarch Don Vito Corleone (Marlon Brando) and later his son and successor Michael (Al Pacino).

Though not the main character, James Caan’s Santino “Sonny” Corleone is at the center of some of the movie’s most pivotal and iconic scenes. It is hard to think of anyone more perfect for the role of Sonny than James Caan, who was able to channel pure anger and passion with this ill-fated character.

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James Caan and Billy Dee Williams in Brian's Song

(Image credit: ABC)

Brian’s Song (1971)

Based on a true story, the landmark 1971 ABC TV movie, Brian’s Song, tells the story of Brian Piccolo (James Caan) and Gale Sayers (Billy Dee Williams) as they form an unbreakable bond as teammates on the Chicago Bears, a friendship that is later put to the ultimate test.

One of the best sports movies of all time, Brian’s Song is also one of the most emotional you’ll see in the genre. And after watching the moving performances by Caan and Williams, it’s easy to see why. Especially when it comes to the film’s final act.

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Kathy Bates and James Caan in Misery

(Image credit: Columbia Pictures)

Misery (1990)

In Rob Reiner’s 1990 adaptation of Stephen King’s Misery, novelist Paul Sheldon (James Caan) is “rescued” by Annie Wilkes (Kathy Bates), a former nurse and his biggest fan who has a twisted and incredibly violent manner of taking care of the injured author following a car crash.

This disturbing psychological thriller is mostly remembered for the brilliantly diabolical performance by Bates (it earned her and Oscar), but Caan’s portrayal of the famed novelist is right up there in terms of acting. Watching him come up with different ways to escape his captor while also going through a great deal of physical and emotional trauma is beyond riveting.

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Amy Sedaris, James Caan, and Will Ferrell in Elf

(Image credit: New Line Cinema)

Elf (2003)

Upon learning he wasn’t actually born at the North Pole, Buddy the Elf (Will Ferrell) goes on an odyssey to find his long-lost father, a children’s book publisher named Walter Hobbs (James Caan), in Jon Favreau’s modern Christmastime classic, Elf.

One of the great things about Caan’s performance in Elf is the way in which he always looks like he’s about one second away from blowing a gasket and going all Sonny Corleone on Buddy. The cynicism, anger, and animosity in his portrayal really take the movie to the next level.

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James Caan in Thief

(Image credit: United Artists)

Thief (1981)

In Michael Mann’s gritty neo-noir thriller, Thief, James Caan plays a Chicago-based ex-convict who specializes in high-stakes jewelry heists that earn him a lot of cash. With the success comes a reputation that puts him on the radar of a crime boss who offers him a big job that could help him start a new life.

There’s so much that can be said about Thief, and it starts with Caan’s performance. With the role, he finds the balance between being a hot-headed criminal and tender and compassionate man looking for a way out of a life of crime. The argument at the adoption agency (where he says “I’ve got some ABC-type information for you, lady”) is a perfect example of that.

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James Caan in El Dorado

(Image credit: Paramount Pictures)

El Dorado (1966)

After a wealthy tycoon named Bart Jason (Ed Asner) arrives with a plan to kick a family off their land, it’s up to gunslinger Cole Thornton (John Wayne), a young cowboy named Mississippi (James Caan), and the drunken town sheriff (Robert Mitchum) to save the family and the town in Howard Hawks’ El Dorado.

Although El Dorado is very much a John Wayne movie both in style and the focus on “The Duke” and his character, this beloved classic also served as a great launching point for the young Caan.

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James Caan in The Gambler

(Image credit: Paramount Pictures)

The Gambler (1974)

On the surface, Axel Freed (James Caan) seems like your everyday college professor, but the New York City intellectual is secretly battling a severe gambling addiction. After years of racking up losses with various bookmakers, Freed is given one last shot to wipe out his debt or pay the consequences.

Karel Reisz’s 1974 anxiety-inducing drama plays a lot like Uncut Gems nearly 50 years earlier in that it centers on a character you can’t help but love despite never learning from his mistakes. Though less over-the-top and explosive than some of his other roles, Caan’s performance is incredibly emotional and memorable.

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James Caan and Nicolas Cage in Honeymoon in Vegas

(Image credit: Columbia Pictures)

Honeymoon In Vegas (1992)

After losing a high-stakes poker game and agreeing to let a notorious gambler (James Caan) spend the weekend with his fiancée (Sarah Jessica Parker) to pay off the debt, private eye Jack Singer (Nicolas Cage) embarks upon a frenzied odyssey to get her back in Honeymoon in Vegas.

Andrew Bergman’s 1992 romantic comedy features a hilarious performance by Caan that channels some of his earlier crime-based work and adds a nice touch to it, which creates an incredible character that you sort of almost root for throughout the movie.

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James Caan and Marsha Mason in Cinderella Liberty

(Image credit: 20th Century Fox)

Cinderella Liberty (1973)

Sailor John Baggs Jr. (James Caan) meets a prostitute named Maggie Paul (Marsha Mason) while waiting to be reassigned to another ship following a medial evaluation. But, as falls in love with the woman, Baggs begins to have concerns about her line of work, adding further complications to their rocky relationship.

Caan was mostly known for his boisterous and hard-edged roles that showed him losing his cool without a moment’s notice, which makes his tender and loving performance in Mark Rydell’s Cinderella Liberty such a treasure.

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Luke Wilson and James Caan in Bottle Rocket

(Image credit: Sony Pictures Releasing)

Bottle Rocket (1996)

Just as gets out a mental hospital, Anthony (Luke Wilson) finds himself wrapped up in a plan orchestrated by his best friend Dignan (Owen Wilson) to start an epic crime spree. But the pair soon find out supporting themselves through a life of crime isn’t as easy as they expected.

Like the other great Wes Anderson movies, the 1996 crime comedy, Bottle Rocket, is full of eccentric and quirky characters like James Caan's Mr. Henry, the owner of a landscaping business and crime boss who steals every scene in which he’s featured. 

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James Caan and Barbra Streisand in Funny Lady

(Image credit: Columbia Pictures)

Funny Lady (1975)

Herbert Ross’ 1975 musical comedy, Funny Lady, centers on the relationship shared by stage sensation Fanny Brice (Barbra Streisand) and showman Billy Rose (James Caan) as their success in show business leads to issues in their personal lives.

The pairing of Streisand and Caan in Funny Lady is really what makes this movie work as well as it does. The chemistry shared by the two is electric and provides for some truly amazing scenes, both humorous and dramatic. 

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James Caan in Rollerball

(Image credit: United Artists)

Rollerball (1975)

Set in a future where corporations control everything from access to knowledge and personal freedoms, rollerball has become society’s most popular sporting event. When Jonathan (James Caan), the star of the Houston team refuses to retire, the corporate overlords change the rules of the game in the hope of killing him off.

Norman Jewison’s 1975 sci-fi sports film, Rollerball, is an incredibly gritty affair with a great deal of biting social commentary about corporations, freedom, and violence that is propelled by Caan’s portrayal of a man fed up with being controlled who takes a stand for what’s right.

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James Caan in A Bridge Too Far

(Image credit: United Artists)

A Bridge Too Far (1977)

Richard Attenborough’s 1977 military epic, A Bridge Too Far, follows American and British forces as they plan to take back a road leading from the Netherlands to Germany in the height of World War II. But, the mass of soldiers soon discover the plan isn’t going to be as easy or painless as they once thought.

There are few military dramas that feature a cast as noteworthy as A Bridge Too Far, which boasts the likes of Sean Connery, Michael Caine, Robert Redford, Ryan O’Neal, Anthony Hopkins, and James Caan as Staff Sergeant Eddie Dohun. Caan’s performance is particularly stunning, especially the scene where he goes to great lengths to save a soldier.

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The world lost one of its most treasured screen legends with the passing of James Caan, but we should take solace in knowing he gave cinema so many great, memorable performances while he was here. And, to quote the ending of Brian's Song, we'll remember him as he lived. How he did live...

Philip Sledge
Philip Sledge

Philip grew up in Louisiana (not New Orleans) before moving to St. Louis after graduating from Louisiana State University-Shreveport. When he's not writing about movies or television, Philip can be found being chased by his three kids, telling his dogs to stop yelling at the mailman, or yelling about professional wrestling to his wife. If the stars properly align, he will talk about For Love Of The Game being the best baseball movie of all time.