The Godfather

The 10 Best James Caan Movies, According To Letterboxd

Legendary actor James Caan passed away this week, leaving behind a legacy of iconic movie roles from The Godfather to Stephen King's Misery.

Legendary actor James Caan, who was most famous for his role in The Godfather with a career full of other great films, passed away at the age of 82 this past week. His final film Fast Charlie is set to be released posthumously in 2023, and the actor had a rich and prolific career working in films since the 1960s.

There has been an outpouring of support for the late actor, whose estate said that they “appreciate the outpouring of love and heartfelt condolences” that has come from fans and colleagues all over the world, according to Sky News. Caan’s career will go down in history as one of the great actors in the history of cinema.

Bottle Rocket (1996) – 3.5/5

Bottle Rocket

Bottle Rocket was the first film from now-iconic director Wes Anderson, featuring breakout performances from Luke and Owen Wilson. Caan played the role of Mr. Henry in the film, a casting choice that showed the actor’s knack for making artistic over commercial decisions, as he was working with a relatively unknown Anderson at the time.

RELATED:Every Wes Anderson Movie, Ranked According To Rewatchability

According to the Dallas Observer, a 1995 profile of Wes Anderson showed Caan’s personality to be quite playful on the set of the film, most notably in his practicing of martial arts moves with Owen Wilson. Caan brought a perfect mix of gritty intensity and affectionate charisma that was needed for the role and has helped make Bottle Rocket a cult classic.

Irma La Douce (1963) – 3.6/5

James Caan in Irma la Douce

Though Caan is uncredited in the film, his first-ever role in a feature film came with Billy Wilder’s Irma La Douce, a romantic comedy based on the musical of the same name. Caan had worked in television up to that point in the 1960s but took a small role in the legendary filmmaker’s movie that started his film career.

Although he played a tiny role as an American soldier in Wilder’s film, the movie helped launch Caan into silver screen stardom. He spent the rest of the 1960s continuing to work with prestigious filmmakers like Wilder, including Howard Hawks and Sam Peckinpah, which lead to his breakout as a movie star in the 1970s.

The Gambler (1974) – 3.6/5

James Caan in The Gambler

The Gambler was a crime film that starred James Caan as Axel Freed, an English professor in New York City with a gambling addiction that spirals out of control as the film progresses. Caan has listed the film as one of his own personal favorites in his filmography, emphasizing the difficulty of playing the complicated character.

The film received mostly positive reviews when it was released, but Caan was universally praised for his performance and received a nomination at the Golden Globes for the role. The film is available to stream on the Criterion Channel and holds up as one of the best performances of Caan’s career.

El Dorado (1966) – 3.7/5

John Wayne in El Dorado

El Dorado was somewhat of a breakout role for Caan’s career in feature films, as he played a supporting role in the Western by legendary American filmmaker Howard Hawks. Caan held his own alongside some of the best actors in film history, as John Wayne and Robert Mitchum played the two starring roles in the film.

RELATED:20 Best John Wayne Movies, Ranked According To IMDB

Showbiz Cheat Sheet states that Caan’s reputation for being great to work with and fun on set may have begun with El Dorado, as Caan and Wayne were playing pranks on each other often during the filming. The film is one of the most memorable roles that Caan took on, and is a favorite in the actor’s filmography among many fans.

Detachment (2011) – 3.8/5

James Caan in Detachment

Detachment is a smaller and somewhat forgotten movie in Caan’s filmography, directed by filmmaker Tony Kaye who is most famous for making American History X. The film follows a substitute teacher, played by Adrien Brody, who goes from school to school without ever staying long enough to have any attachments.

Letterboxd users’ reviews focused on how emotional and sad the film is, thanks to grounded performances by Brody, Caan, and the rest of the cast. The film is available to stream for free on Peacock, and Letterboxd reviews have been flooding in with praise for Caan’s performance since the news of his passing on Thursday.

Misery (1990) – 3.9/5

james caan misery with kathy bates

James Caan starred in Misery, based on a Stephen King novel of the same name, about a novelist who finds himself at the mercy of an obsessive fan after he is left immobile in a car crash. The film was Caan’s collaboration with iconic filmmaker Rob Reiner for one of his best movies, who was also behind classics like When Harry Met Sally and The Princess Bride.

The film was a smash hit at the box office and among critics with many praising the performances of Caan and Bates in this heartstopping thriller. Letterboxd users describe his performance as “intense” and “frequently hilarious” and the film is still considered one of Caan’s best.

Thief (1981) – 4.0/5

james caan in michael mann's thief

Thief is the feature film debut by legendary action director Michael Mann and is an action thriller filled with neo-noir aesthetics. James Caan stars in the film as Frank, a professional safecracker who is trying to escape from his criminal ways, and the film has developed into a cult classic despite its modest box office.

RELATED:10 Best Michael Mann Movies, Ranked According To Letterboxd

Caan’s decision to star in the debut films of future legends like Anderson and Mann seems almost prophetic and shows the care and passion that the actor had for the art of cinema. Among his extensive filmography, it is easy to say that Frank was one of James Caan’s best roles.

Dogville (2003) – 4.1/5


James Caan had a small role in one of Lars Von Trier’s best movies Dogville, an experimental drama film about a woman who is on the run and hiding from mobsters. Nicole Kidman plays the leading role, and Caan has a supporting character alongside Paul Bettany, Stellan Skarsgaard, and others.

Caan is only in one scene of the film, and Twitter users were taking to the site to celebrate him earlier this month when someone prompted fans to list the best performance from an actor who only appears once. Caan is incredibly memorable in his short appearance and shows off his incredible screen magnetism in the role.

The Godfather Part II

godfather 2 ending family dinner

James Caan has only a small part in The Godfather Part II, reprising his role in the original film with just a short cameo in the very final scene of the movie. Caan plays Sonny Corleone, the brother of Al Pacino’s Michael, in the series, and his character was killed in the first film.

The director of the film Francis Ford Coppola put out a touching tribute to the late actor saying “Jimmy was someone who stretched through my life… He will always be my old friend from Sunnyside, my collaborator, and one of the funniest people I’ve ever known.”

The Godfather

Sonny Corleone laughing in The Godfather

Though there is some debate between fans as to whether The Godfather Part II is better than the original, Letterboxd fans prefer The Godfather. Caan’s legacy as an iconic actor truly began in The Godfather, as his portrayal of Sonny Corleone is the heart of the first half of the classic film.

No character in Caan’s filmography comes close to touching how iconic his portrayal of Sonny is, and the role will be the most remembered part of his career as an actor. His performance stands out among other stellar acting from Pacino and Marlon Brando, and he is a crucial part of one of the best films of all time.

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