James Caan’s 10 Best Film Roles

James Caan died today.

The film and stage actor appeared in nearly 100 movies, including some of the most iconic motion pictures of the past 50 years.

With so many juicy performances to choose from, here’s my top-ten list of James Caan’s most memorable film roles:

1. The Gambler (1973) — Caan was born to play Axel Freed, the Ivy-League university professor-turned-raging-gambling addict.  Caan brings the perfect balance of intensity, humor, street smarts, and compassion to a challenging role.  Most movies portray gamblers unrealistically, but Caan embodies his diverse character with seemingly split personalities — respected professor by day and reckless risktaker at night.  Why is The Gambler Caan’s best performance?  Well, he appears in nearly every scene of this two-hour film that builds to a suspenseful climax.  No movie has ever convincingly pulled off the rush of risk and gambling addiction, but Caan somehow manages to reveal the psyche of a compulsive gambler.

2. The Godfather (1972) — Mario Puzo’s immaculately-written fictional character Santino “Sonny” Corleone is brought to life by Caan, which is considered by many to be his best career performance.  Perhaps rightfully so, due to The Godfather being bronzed as one of the greatest films ever made. Caan’s explosive temper is in stark contrast to the cooler heads of the Corleone crime family and leads to his bloody demise.

3. Cinderella Liberty (1973) — This is one of the most underrated films of the 1970s, and James Caan absolutely nails the lead role.  He’s a lonely and bored Navy enlisted man who falls in love with a Seattle prostitute played by Marsha Mason.  The love story is doomed from the start, of course, but John Baggs, Jr. comes to care deeply about more than himself and gradually develops a close bond with the prostitute’s illegitimate (and Black) son.  It’s the unlikeliest of pairings, as Caan becomes the boy’s de facto father figure.  This might be Caan’s most tender performance of many, which is really saying something given how many hard-edged but vulnerable characters he played.

4. Rollerball (1975) — A futuristic movie about a twisted bloodsport with Caan cast in the role of a world-famous superstar athlete.  At the time it was released, Rollerball was considered a violent movie with shocking scenes of intense brutality — all in the quest for fame and fortune.  It’s a sort of Gladiator for the 21st Century.  Now, we see this film (set in 2018) very much predicted the future.

5. Thief (1981)— Continuing with Caan’s typecast as a smart tough guy constantly teetering on the emotional edge and pushed to his physical boundaries, Caan plays a jewel thief connected to a well-organized crime syndicate.  As he gets more deeply involved in high-tech crimes, he realizes that his life is no longer his own.  That’s when he discovers he can’t just leave and retire from “the company.”  This sets up a raging breakaway showdown between Caan and his criminal overseers.

6. Brian’s Song (1971) — It was this sympathetic out-of-character role in a Made-for-TV movie that made Caan a star and a household name, leading to a huge run of box office blockbusters in which he appeared over the next decade.  Caan played the late Brian Piccolo, a true-to-life Chicago Bears running back who died of cancer in his prime at age 27.  Grown men cried when they watched this movie for the first time, and still cry when we watch it 50 years later.

7. Misery (1990) — One typically doesn’t think of Caan as a best-selling novelist, but he pulled off playing Paul Sheldon masterfully in Misery.  Caan gets injured in an auto accident in rural New England and is “rescued” by Kathy Bates (in her Oscar-winning role).  Dangerously obsessed with Caan and his books, she makes his forced rehabilitation a living hell.  A compelling dark comedy, enhanced by Caan playing against his typecast.

8. Honeymoon in Vegas (1992) — Caan is perfectly cast as the lustful casino executive who is obsessed with Sarah Jessica Parker, a Las Vegas on holiday tourist and the ditzy fiance of man-mess Nicholas Cage.  Caan conspires to steal the girl all for himself thanks to a crooked poker game, one of the funniest such scenes ever made.  Caan doesn’t deviate much from the usual mixed bag of conflicting character traits he brings to every role — including his charm and toughness, always spiced with a bit of chicanery.

9. Lady in a Cage (1964) — This was only Caan’s second film role, and he’s cast opposite the legendary Olivia de Havilland, who is a wealthy socialite who gets trapped and then terrorized inside her mansion for the duration of the movie.  Caan, the bad guy, is a burglar.  Caan shows early gravitas in this unusual performance.  He could have just gone the one-dimensional route and played the young punk in a predictable fashion, so typical of films made from the time, but Caan slowly peels off more of himself than we expect.

10. Gardens of Stone (1987) — This was one of director Francis Ford Coppola’s lesser-known films, a flawed movie, but well carried by Caan in the starring role. He plays the battled-hardened Army Sgt. Clell Hazard, who is assigned to be in charge of the day-to-day operations of the Old Guard, which is the U.S. Army’s Honor Guard.  His unit provides the ceremonial honor guard for the funerals of fallen soldiers and also protects the Tomb of the Unknown Soldier in Arlington.  An interesting movie made more intriguing with Caan in the lead.