20 Best James Caan Movies, According to IMDb

James Caan passed away at the age of 82 in July 2022, leaving behind a sizable filmography that contained numerous iconic movies belonging to a wide variety of genres. He began his film career in the 1960s, with his body of work ultimately lasting about 60 years, given the final movie he was featured in, Fast Charlie, premiered in October 2023.

He was incredibly prolific as an actor, with more than 100 acting credits to his name over the space of six decades. The following movies of his are the greatest according to average ratings from users on IMDb, starting below with some of the decent to good films he appeared in, and progressing up to the essential classics he starred in, and often helped elevate.

20 ‘The Way of the Gun’ (2000)

IMDb Rating: 6.6/10

Some years before he became known for teaming with Tom Cruise on numerous movies, including several Mission: Impossible films, Christopher McQuarrie made his feature film debut with The Way of the Gun. It’s a fairly uncompromising and in-your-face crime/action movie, and centers on two criminals who land in hot water after kidnapping someone they really shouldn’t have.

Their target is a surrogate mother who’s carrying the child of a terrifyingly powerful man, played by James Caan, which is where their troubles – and the main plot – kick in. It’s fairly mean-spirited and edgy as a film, feeling like a product of its time, but it has a good pace, strong performances, and solid visuals, with the action scenes in particular being well-shot.

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19 ‘Rollerball’ (1975)

IMDb Rating: 6.6/10

Rollerball is one of those science fiction movies that was once set in the future, but is now technically set in the past, thanks to the unrelenting passage of time. The year is 2018, and the titular (fictional) sport is the focus of the film, with it being a particularly violent one that’s used by corporations in control to implicitly discourage acts of rebellion or non-conformity.

James Caan plays Rollerball’s central character; a player of the game who one day decides to stand up against those who seek to control him and everyone else. It’s solid stuff, and pairs well with another ahead-of-its-time sci-fi action/satire film released in 1975 about games in a violent dystopia: Death Race 2000, featuring a young Sylvester Stallone.

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18 ‘Cinderella Liberty’ (1973)

IMDb Rating: 6.7/10

While it’s one of the more obscure James Caan movies of the 1970s (a decade where the actor was arguably at his peak), Cinderella Liberty seems nonetheless well-liked by those who’ve seen it and rated it on IMDb.

It’s based on the novel of the same name by Darryl Ponicsan, who also wrote the screenplay here, and tells a story about the unlikely romance that blossoms between a sailor and a prostitute. Coincidentally, it was released the same year as another film adaptation of Ponicsan’s work: The Last Detail (starring Jack Nicholson), though he didn’t do the adapted screenplay in that instance.

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17 ‘Lady in a Cage’ (1964)

IMDb Rating: 6.7/10

Containing a great, simple premise for a thriller, Lady in a Cage is a little by-the-numbers, but nonetheless engaging. The title does ultimately do a good job of summarizing the plot, seeing as the film centers on a widow who becomes trapped in an elevator inside her house, and then becomes the target of several home invaders who torment and threaten her.

It was James Caan’s first credited role, and he shines here as one member of the trio who break into the mansion. Caan and the film’s lead, Olivia de Havilland, are successful in elevating Lady in a Cage to a considerable extent, making what would otherwise be a fairly ordinary thriller into something better than average.

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16 ‘The Rain People’ (1969)

IMDb Rating: 6.8/10

A few short years before they collaborated on a certain legendary crime movie from 1972, Francis Ford Coppola and James Caan worked together – as director and actor, respectively – for The Rain People. This 1969 film is a grounded road movie/drama about various lonely people trying to find human connection with others, despite the obstacles life’s thrown their way.

It’s all very subdued in a New Hollywood kind of way, but it largely works and stays absorbing, even with the sometimes uneventful plot and patient pacing. Caan really excels as a college football star grappling with the long-term effects of a serious head injury, with his role here showing his range more than just about any other performance of his from the 1960s.

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15 ‘Middle Men’ (2009)

IMDb Rating: 6.8/10

While Middle Men wasn’t particularly well-received by critics, it has picked up a considerable amount of support from users on IMDb. It also has something of a controversial story behind it, given it was a box office flop and was also notoriously produced by Christopher Mallick, with the film’s story being loosely based on his own experiences.

Those experiences included being instrumental in introducing pornography onto the internet, as well as developing a system to allow credit card transactions online to enable people to view such material. Caan’s part of an ensemble cast that also includes Luke Wilson and Giovanni Ribisi, with Middle Men being overall not as bad as its critical reception may have made it sound.

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14 ‘This Is My Father’ (1998)

IMDb Rating: 6.9/10

This Is My Father has a fairly strong IMDb rating, though it also has considerably fewer ratings than most other James Caan movies that are well-liked among the site’s users. Its title referencing family is fitting, considering it’s a movie that stars Aidan Quinn, with its writer/director being his younger brother, Paul Quinn.

It’s a family drama and a romance film, and centers around a man’s quest to discover who his real father might be, and the inevitable personal journey he undertakes along the way. The film’s events take place during both the 1930s and 1990s, with it being an interesting and well-told story about one Irish family over generations.

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13 ‘Bottle Rocket’ (1996)

IMDb Rating: 6.9/10

Two years before directing the critically acclaimed coming-of-age film that was Rushmore, Wes Anderson made his feature debut with the still well-liked Bottle Rocket. It was an expanded, feature-length version of a short film Anderson had directed in 1994, with brothers Luke and Owen Wilson appearing in both (Owen Wilson was also credited as a co-writer with Anderson for each version).

Bottle Rocket’s a small-scale and entertaining blend of comedy and crime, centering on three friends who plan to pull off a series of robberies before meeting up with a mysterious criminal figure known as Mr. Henry. James Caan plays this older criminal, and shines in a solid supporting role, bringing prestige to this early Wes Anderson movie by being the most well-known actor (at the time) to appear in it.

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12 ‘The Gambler’ (1974)

IMDb Rating: 7.1/10

Alongside James Caan, Paul Sorvino was another well-known crime movie actor who also sadly passed away in July 2022. Nearly 50 years earlier, the two had starred in an underrated crime/drama movie together called The Gambler, which centers on a man with a gambling addiction who’s unable to stop, no matter the losses he suffers.

The film follows the rocky relationships he has with family members, his girlfriend, and, eventually, some loan sharks who don’t exactly take kindly to people who are unable to pay their debts. It’s an honest and uncompromising look at addiction to something that’s not illicit in nature, with Caan’s performance in the lead role here being particularly strong and believable.

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11 ‘Elf’ (2003)

IMDb Rating: 7.1/10

When it comes to discussing the most iconic Christmas movies of the 21st century so far, Elf’s one that’s likely to be brought up pretty much every time. It’s about a man who’s been brought up in the North Pole, believing he’s an elf, and what happens to him when he travels to New York City to find and meet his real father.

Will Ferrell’s the lead here, and it was perhaps his first truly successful lead role in a movie, after he’d spent the previous years on Saturday Night Live and in various supporting film roles. It also might be the most well-known post-2000 James Caan role, with him turning in a very strong performance as the protagonist’s father, with Elf also standing out for being the rare family-friendly Caan movie.

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10 ‘Bolero’ (1981)

IMDb Rating: 7.3/10

A surprisingly epic movie musical that runs for almost three hours, Bolero is also sometimes known as Les Uns et les Autres, which translates to The Ones and the Others. It has a huge international cast, and tells an epic story that spans decades; roughly from before the start of the Second World War and then ending during the 1980s.

With the size of the cast, James Caan is ultimately one of many people featured in the film, but notably takes on two roles here: both a father and his son, which is possible due to the number of years the story spans. It’s an overall interesting and undeniably ambitious movie, and perhaps one of the more underappreciated within Caan’s filmography.

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9 ‘Thief’ (1981)

IMDb Rating: 7.4/10

Michael Mann’s best-known crime movie is probably 1995’s Heat, but many other films of his are worth checking out too, including 1981’s Thief. This one stars James Caan as a skilled safe cracker who’s preparing to do one big final job (as so many protagonists in heist movies aim to do) before retiring for good.

It’s an effortlessly cool and – typical for Mann – a very slick movie, and Caan is excellent in the lead role. Those who like their crime/action/thriller movies simple but satisfying ought to check out Thief, as though it’s relatively well-known to the point where calling it overlooked might not be fitting, it’s still something that’s perhaps under-appreciated to some extent.

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8 ‘A Bridge Too Far’ (1977)

IMDb Rating: 7.4/10

In September 1944, the Allied forces launched one of their most ambitious operations of World War II with what was labeled Operation Market Garden. It was intended to create a way for further Allied forces to invade German territory and potentially bring about an end to the war, with the attempts to mount this operation covered extensively in A Bridge Too Far.

With a runtime of almost three hours and an all-star cast that included Gene Hackman, Robert Redford, Sean Connery, Anthony Hopkins, Michael Caine, and of course James Caan, among many others, it’s a fittingly epic World War II movie. It’s long and a bit old-fashioned, but does prove to be a rewarding watch, and stands as one of the more impressive war movies of its decade.

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7 ‘Brian’s Song’ (1971)

IMDb Rating: 7.5/10

Brian’s Song is a classic sports film tearjerker, and though it’s technically a TV movie, it nevertheless deserves to be included alongside James Caan’s top-rated theatrically-released titles. James Caan plays the title character, and Billy Dee Williams co-stars as his friend, with the story centering on the bond two footballers have, and what happens when one learns he’s dying.

It’s presented in a way that some might feel is a little conventional, but it’s also effective and emotional enough that calling it clichéd feels unfair. Caan and Williams elevate what could otherwise be an ordinary TV movie considerably, with both being key reasons why it’s held in such high regard among feature films made for television.

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6 ‘El Dorado’ (1966)

IMDb Rating: 7.5/10

Not to be mixed up with the 1998 movie about a road, 1966’s El Dorado is a Western starring John Wayne and Robert Mitchum in the lead roles, with James Caan in a supporting role. It follows an unlikely squad of people banding together to help one rancher take on a rival who’s attempting to steal water from the rancher and his family’s property.

Caan holds his own against the more established lead actors here, and El Dorado is ultimately a satisfyingly made and easy-to-watch classic Western. It might not convert people who aren’t already crazy about Westerns released decades ago, but it’s a well-oiled machine of a movie that’ll undeniably please fans of the genre.

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5 ‘Detachment’ (2011)

IMDb Rating: 7.7/10

Detachment is a drama that stars Adrien Brody in the lead role. In the film, he plays a substitute teacher who has to get by with jumping around between classrooms, with the film exploring the way this challenges him in forming bonds with other teachers and the huge number of students he teaches.

The cast of Detachment is impressive, as beyond Brody and Caan, other actors here include the likes of Lucy Liu, Christina Hendricks, and Bryan Cranston (coincidentally, the latter two were also featured in the cast of another 2011 movie: the moody and stylish crime/thriller, Drive).

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4 ‘Misery’ (1990)

IMDb Rating: 7.8/10

The central premise of Misery is quite genius in its simplicity, with it centering on one writer and his nightmarish, ultimately gruesome encounter with a dangerously passionate fan of his. The writer (Caan) is seriously injured in a car accident, and at first, one of his fans (Kathy Bates) appears willing to nurse him back to health.

Unluckily for him, she actually wants to force him to change one aspect of a story he wrote that she doesn’t like, and lashes out violently when it becomes apparent that he won’t. Caan is great as the victim here, but it’s Bates who does ultimately shine with the flashier role, and she ended up winning an Oscar for her captivating and utterly menacing performance.

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3 ‘Dogville’ (2003)

IMDb Rating: 8.0/10

Dogville is, without a doubt, one of the most acclaimed movies directed by the famous/infamous Lars von Trier. It also might well be one of his most challenging works to date, given its unusual presentation, with all the action playing out on a soundstage that’s almost completely empty, and intended to represent the titular town.

The plot concerns a woman who’s on the run from the mob, and attempts to hide out in the town of Dogville, with the film detailing her experiences with the unusual people who live there. Though the film’s strange, von Trier still managed to attract a large number of big-name actors to the project, with Nicole Kidman leading a cast that includes the likes of Caan, Lauren Bacall, John Hurt, Paul Bettany, and Stellan Skarsgård.

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2 ‘The Godfather: Part II’ (1974)

IMDb Rating: 9.0/10

The Godfather: Part II is justifiably considered one of the greatest movie sequels of all time, if not the greatest. It continues the story of Michael Corleone, who now finds himself as the head of the criminal/family empire, all the while flashbacks provide insight into how his father, Vito Corleone, came to America and established himself as the man he’s shown to be in the first movie.

It’s darker than the first movie, and considerably more epic, thanks to the lengthier runtime and the fact it’s both prequel and sequel. James Caan has a fairly small role, only showing up in one flashback right near the film’s end, but it’s a tremendously powerful scene that helps The Godfather: Part II feel like a suitably powerful second half to the epic story told across two films (The Godfather: Part III, on the other hand, is more contested and perhaps more of an added epilogue).

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1 ‘The Godfather’ (1972)

IMDb Rating: 9.2/10

Yet for as great as The Godfather: Part II is, The Godfather (1972) is sometimes considered the best of the two, and that at least seems to be the case for IMDb users. This was the film that began it all for the Corleone family on the big screen, proving to also be a breakout success for director Francis Ford Coppola, and being a pivotal film in establishing (or solidifying) the talents of numerous cast members, including Al Pacino, James Caan, Diane Keaton, and Robert Duvall.

The character of Sonny Corleone is the role that James Caan’s best known for, and it earned him his sole Oscar nomination (for Best Supporting Actor). Caan brings an unbelievable intensity and anger to the role, with his character’s inevitably tragic arc in this original film being one of the most memorable parts of it. It’s hard to top The Godfather in general, and of James Caan’s numerous performances, it’s understandable why this is usually considered his most noteworthy.

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