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The 7 Best And 7 Worst James Caan Movies Ranked

As an actor, it's hard to retain a consistent career that lasts decades, with hits often scattered throughout a filmography, but James Caan made it look easy. Best known for his serious dramatic work as Sonny Corleone in Francis Ford Coppola's "The Godfather," Caan's talents spanned various genres and styles. Throughout his career, Caan stretched his acting chops by starring in some pretty great comedies, science-fiction films, action movies, Westerns, and one of the most well-known Christmas films of all time, "Elf." There was no limit to the types of characters that Caan could commit himself to, and that's part of what made him so great to watch.

Before his death in July 2022, Caan made a name for himself by working with some of the best directors out there such as Coppola, Wes Anderson, Rob Reiner, Michael Mann, Jon Favreau, Lars von Trier, Howard Hawks, and a host of others. Though, with nearly 150 different acting roles in his filmography, they couldn't all be hits. In the 2010s, Caan made a slew of bad movies that, while they certainly didn't tarnish his career, didn't do him any favors either. To help you weed through Caan's extensive filmography, here's our list of the seven best and seven worst James Caan movies out there.

Best: The Godfather (1972)

"The Godfather" is widely considered by many to be the greatest film ever made. With intense performances, clever writing, and incredibly detailed direction, Francis Ford Coppola really outdid himself with this instant classic. Shining bright as ever in this film — the cast of which also features Marlon Brando and Al Pacino — is James Caan as the hotheaded heir to the Corleone throne, Sonny. Completely committing to his role as a heavy-tempered mobster, Caan could be somewhat erratic on screen, but only in the best ways. Though his character doesn't make it out of the film alive, his brief cameo in "The Godfather, Part II" reminds us exactly why.

Ironically, Caan wasn't always as happy with his role in "The Godfather" as we might be today. In fact, he actually walked out of the screening of the film because he was so upset that Coppola cut out an entire scene he shared with Robert Duvall. Although Caan was ultimately grateful for his experience with Coppola (as evidenced by his brief return for the sequel), we may never know if he ever went back and finished the film for himself. There's no doubt that "The Godfather" is one of Caan's best dramatic works, and his excellent performance is only further emphasized by that of his on-screen co-stars.

Worst: The Outsider (2014)

In his later years, James Caan took on some less-than-stellar film roles, including in the critically reviled 2014 film "The Outsider." While Caan's own performance is reliably solid no matter which film he's starring in, that doesn't mean that the quality of the overall production is anything to write home about. In this action-crime drama, Caan portrays Karl Schuster, the villainous CEO of a tech company who is responsible for the abduction of military contractor Lex Walker's (Craig Fairbrass) daughter. Walker, with the help of Detective Michael Klein (Jason Patric of "The Lost Boys" fame), fights to find his daughter and take down Schuster in the process.

Although the film has its few moments of exciting action, the overall plot feels a lot more like an extended episode of "NCIS," "Criminal Minds," or any other standard television procedural, with little substance beyond the surface. Of course, Caan himself is excellent as always in his sniveling criminal role here, but even his solid performance doesn't save this action flick from being a nigh-disaster. 

Best: Elf (2003)

One of the most beloved Christmas movies of all time, 2003's "Elf" is a delightful film that shows not just the full comedic range of Will Ferrell, but also that of James Caan himself. Playing the old miser of a children's book publisher Walter Hobbes, Caan's work with Ferrell is some of the best on-screen chemistry you could hope for. As Buddy the Elf (Ferrell) travels from the North Pole to the "magical land" of New York City, he hopes to reconnect with his real father (Hobbes) and build a new life as an actual human being. In addition to Ferrell and Caan, the film's cast also includes Ed Asner as Santa Claus, Zooey Deschanel as Jovie, and Mary Steenburgen as Hobbes' wife Emily.

The film's clever aesthetics help this Christmas classic stand out as a modern triumph with clear ties to the holiday specials of old. There's no doubt that director Jon Favreau had a clear and distinct vision for what he hoped "Elf" would be, and judging by the film's overall success and place in our collective consciousness, he got everything he wished for. Watching Caan's Walter Hobbes go from being one level down from Scrooge to becoming a real father to his children is incredibly heartwarming. It's a story we look forward to revisiting every December.

Worst: That's My Boy (2012)

If you forgot that James Caan had a supporting role in the overtly ridiculous Adam Sandler comedy "That's My Boy," then you were right to do so (and our apologies for bringing it up). Now that we've all remembered as much, though, let's revisit this story about a young man named Todd Berger (Andy Samberg) whose father is a slightly older man named Donny (Sandler) who had him when he was in middle school after an inappropriate relationship with a teacher. Yeah, that's what "That's My Boy" is about: a father and son reconciliation as Todd is about to get married. And who better to marry him and his unfaithful bride but James Caan?

Although Caan's Father McNally isn't in much of the film, his scenes happen to be pretty memorable, especially the scene between the priest and Andy Samberg's Todd where McNally beats the living daylights out of the younger Berger. The initial shock value is hilarious, but don't let that scene fool you, the rest of the film is a real miss. "That's My Boy" certainly reminds us of Caan's chops as a comedic actor; it's just a real shame that the quality of the rest of his comedies isn't really there.

Best: Misery (1990)

Based on the classic Stephen King novel of the same name, Rob Reiner's "Misery" is a masterclass in acting that truly deserves all of the hype and praise. Starring James Caan as romance novelist Paul Shelton and Kathy Bates as the fanatical nurse Annie Wilkes, "Misery" is a delight, just not for the characters involved. Often considered one of the best Stephen King adaptations of all time, the film follows Shelton after he's "saved" from a blizzard and a car wreck by Wilkes, only to realize that he's in much more danger with her than he would've been on his own.

Bates' work in this film might've earned her a well-deserved Academy Award for best actress, but Caan's performance as the desperate Paul Shelton is just as convincing. As Shelton tries his best to escape the clutches of the obsessive nurse, we find ourselves just as unsettled — if not more so — as he is, hoping beyond hope that he'll make it out alive. As far as James Caan films go, "Misery" is one of the absolute best and accessible to even those who aren't fans of King's works — as long as you've got a strong enough stomach for the infamous hobbling scene, that is. 

Worst: Wuthering High School (2015)

"Wuthering High School," a television film based on the 1847 Emily Brontë novel "Wuthering Heights," is a story of revenge and obsession. The film takes the premise of Brontë's original story and updates it to modern-day Malibu, California — and let's just say that the scenery change from dark and dreary to "always sunny" doesn't exactly work. So where does James Caan fit into all of this? Well, he plays Mr. Earnshaw, of course, the father to the protagonist Catherine "Cathy" Earnshaw (played here by Paloma Kwiatkowski).

It's important that we don't understate Caan's performance here. Playing a concerned father, Caan knocks his role in "Wuthering High" out of the park in a way that only he can, and his chemistry with Paloma Kwiatkowski really sells their roles as father and daughter. Of course, the melodrama of "Wuthering High" brings it down a peg or two, and unless you're currently in high school yourself you might not see as much value in this film as you might in others on Caan's filmography. Regardless, if you really want to see Caan play a struggling father, there are far better movies on this list.

Best: Thief (1981)

It's a classic story. The seasoned criminal falls in love and decides to leave his life of crime, but in order to get out, he has to perform one final job to set up their future life together. Sound familiar? Well, Michael Mann's "Thief" practically invented the trope for modern audiences, and James Caan sold it to everyone with a rock-solid performance as Frank that'll make you wish you were half as cool as this character. Set in Chicago, the film shows Frank working hard to maintain the life he's worked to build while trying to move on to greener pastures. Alongside Caan, the film stars entertainment icons Jim Belushi as Frank's friend Barry, Willie Nelson as Frank's mentor "Okla," and Tuesday Weld as Frank's wife Jessie.

"Thief" is a pretty exceptional picture and a masterclass in neo-noir filmmaking. Caan's work as Frank in the film reminds us that this is the type of character he was born to play. Although "Heat" is Mann's most famous motion picture (and for good reason), "Thief" deserves a lot more credit for showcasing Caan as such a powerful leading man. 

Worst: The Throwaways (2015)

Unfortunately, just because a movie has a decent cast doesn't mean it's going to be good, and the title of 2015's "The Throwaways" is an all-too-apt descriptor for this motion picture. A 2015 spy-heist Crackle Original Movie, "The Throwaways" centers around a young hacker named Drew Reynolds (Sam Huntington of "Being Human" fame) who is conscripted into the C.I.A. by Lt. Col. Christopher Holden (Caan) into a team of — you guessed it — "throwaways" who are sent on their own spy mission. The team also consists of "Supergirl" star Katie McGrath, "Entourage" actor Kevin Dillon, and "The Last Kingdom" star Christian Hillborg.

The film feels more like a 90-minute pilot for a continuing spy series rather than a stand-alone film (it even has its own post-credits scene) — and perhaps it might've been a better series than a movie. Caan's work as Holden is as consistent, but what really stands out here is his chemistry with Sam Huntington (an underrated actor in his own right). While the rest of the movies listed here are either excellent or completely forgettable, "The Throwaways" is somewhere in between.

Best: El Dorado (1966)

One of James Caan's earliest film roles just so happens to be in one of his best films. "El Dorado," a John Wayne western, features Caan as the young gunslinger Alan Bourdillion Traherne aka "Mississippi" alongside the Duke's Cole Thornton and Robert Mitchum's Sheriff J.P. Harrah. "Mississippi" is essentially Thornton's new sidekick, willing to follow the gunslinger to the death. With a plot incredibly similar to other Howard Hawks films like "Rio Bravo" and "Rio Lobo" (which also starred Wayne in the lead role), the film follows Thornton as he travels to help Sheriff Harrah deal with a dispute between neighboring ranchers.

In the film, Caan holds his own next to Hollywood legends like Wayne and Mitchum, with a healthy energy that balances these two veterans out. "El Dorado" might not be the most memorable of Wayne's heavy filmography, but it makes it onto the best of Caan's thanks to his youthful vigor, which is refreshing given the roles he'd take on later in his career. The pic proves that he was just as solid in the earliest points of his career as in the later years, plus it's just plain fun watching him and the Duke hold their own against the tide.

Worst: Mickey Blue Eyes (1999)

In 1999, James Caan starred opposite Hugh Grant in a romantic comedy crime film called "Mickey Blue Eyes," and it's a doozy. An apparent parody of the gangster genre of films — Grant's character even notes the need to watch "Goodfellas," "Casino," and "The Godfather" movies — this isn't one of Caan's best, though there are some clever jokes and moments between him and Grant in there that make it somewhat enjoyable. The film itself follows Michael Felgate (Grant) as he inadvertently becomes a part of his soon-to-be father-in-law's criminal empire as "Mickey Blue Eyes." Trust us, it sounds funnier than it is.

If you're a die-hard fan of mobster movies (or Grant's movies for that matter), then maybe "Mickey Blue Eyes" is for you, especially since nearly a dozen character actors from "The Sopranos" make it into the film at some point or another. After all, Grant and Caan do have some pretty spunky chemistry that lends well to the film; watching Caan's character try to help Grant's talk like a mobster is pretty hilarious. However, other than their buddy-cop demeanor "Mickey Blue Eyes" is mostly pretty forgettable.

Best: A Bridge Too Far (1977)

A film with plenty of incredible star power behind it, "A Bridge Too Far" is a World War II epic that depicts a failed Allied operation called "Operation Market Garden" in which the Allies attempted to take back the Nazi-occupied Netherlands. Based on a book of the same name, the film was directed by Richard Attenborough with a screenplay written by William Goldman of "Butch Cassidy and the Sundance Kid" and "All The President's Men" fame. James Caan stars in the pic as American Staff Sergeant Eddie Dohun alongside an incredible cast consisting of Sean Connery, Michael Caine, Anthony Hopkins, Robert Redford, Gene Hackman, and Dirk Bogarde, among others.

Caan's performance as Dohun is excellent in this film as he truly sells the desperation of these Allied soldiers on the battlefield. However, Caan's absolute best scene in "A Bridge Too Far" actually takes place off the battlefield in the "save my captain" moment where his character pulls the gun on an army medic, forcing him to make sure that his captain is still alive. No doubt one of the best war films ever made, "A Bridge Too Far" is one of those Caan movies that you just can't miss, and one that, quite frankly, you wouldn't want to.

Worst: Con Man (2014)

In one of the more unfortunate films James Caan has been a part of, "Con Man" tells the true story of Barry Minkow (played by Justin Baldoni), a young man who cheats his way to the top and, according to "60 Minutes," would have been one of the first inductees into a "Con Men Hall of Fame." Ironically, the film itself seems to be a bit of a con, and while it's interesting and educational, there's nothing terribly artistic or exciting about "Con Man," no matter how flashy it looks on the surface. In fact, Caan is only in the film for a few scenes.

The film is one part documentary and two parts historical crime drama, and as a result, its structure is quite odd. With a cast that also includes the likes of Mark Hamill ("Star Wars") and Ving Rhames ("Mission: Impossible"), audiences may expect it to be a bit more balanced than it is. However, there isn't a whole lot of substance to the film, and even Caan's depiction of FBI Agent Gamble is pretty bare bones.

Best: Dogville (2003)

One of James Caan's strangest films, "Dogville" is Lars von Trier's avant-garde masterpiece and the first of his presently unfinished "USA – Land of Opportunities" trilogy. The film follows a young woman named Grace Mulligan (Nicole Kidman) who hides out in the small mountain town of Dogville in middle-of-nowhere Colorado. Grace — on the run from the mob, including her father "The Big Man" (Caan) — works the land to survive while the townspeople begin to abuse her. "Dogville" is certainly not for the faint of heart, and while it starts out promising enough, it becomes a dark tale of depravity that reaches some pretty sickening levels.

In the film, which is considered a "masterpiece" by some and "pretentious" by others, Caan's work as the Big Man is everything fans could hope for from this mobster role, albeit all too brief. The movie itself is fascinating given its stage-like set, making "Dogville" feel more like a play than a film, although it is admittedly very disturbing. Still, there are moments of artistic vision and expression that make all the oddities worthwhile in the end, even if we don't get nearly the amount of Caan we were hoping for.

Worst: For The Love of Money (2012)

Of all the bad movies that James Caan has been a part of, his 2012 action crime film "For the Love of Money" is arguably the worst. Based on a true story, the film follows a man (Yehuda Levi) as he leaves his old gangster lifestyle for a new one. It's the popular "Thief" trope all over again, but with fewer trimmings than a Charlie Brown Christmas tree. Besides Caan, the only other well-known "For the Love of Money" stars include "Terminator 2: Judgment Day" legend Edward Furlong and subsequently-disgraced "Arrested Development" star Jeffrey Tambor, both of whom give their all on screen.

Although this is one of the worst films Caan ever starred in, the actor himself still has some pretty memorable moments, especially when his character Mickey screams at his enemies through the phone. While nothing will beat his gangster work from "The Godfather," Caan also has a bloody death scene in "For the Love of Money" that's at least somewhat worthy of his cinematic greatness. 

Only time will tell if some of Caan's worst pictures like this one will gain some sort of cult status, but there's no doubt that his best work will always be celebrated wherever filmmaking is celebrated too.