James Caan performed in films by some of cinema’s greatest directors. Perhaps known best for his role as Sonny Corleone in The Godfather, one shouldn’t miss his performances in films such as Bottle Rocket and Misery. Along with Coppola, Anderson, and Reiner, Caan also worked with Michael Mann, Norman Jewison, James Gray, and more. Caan passed away on July 6th, and our retrospective on his work shines a light on some of our favorite performances from the late actor.

The Rain People (1969)

Francis Ford Coppola’s The Rain People, the last film he would direct before The Godfather, was not a huge financial success or even a critical one at first, though it has attained a warmer reception as time has worn on. Heralded as a feminist counterpart to Easy Rider, The Rain People follows Natalie (Shirley Knight) after she leaves her husband and goes on a journey of self-discovery.

On that journey, she runs into Jimmy “Killer” Kilgannon (James Caan). A star football player, Killer was kicked out of college after suffering a traumatic brain injury. Part of Natalie’s reason for leaving her husband was feeling ill-fit to be a mother or caregiver with Killer awakening that side of her, given how helpless and lost he is, both due to his brain injury and lack of skill-set outside of football. Caan may not be the centerpiece of the film, but he is brilliant. Playing against the tough, macho, and charismatic type he would cultivate in the years to come, he has these puppy dog eyes and innocent tone in his voice that makes him impossible to leave behind, no matter how many times Natalie tries. Caan could have easily exaggerated or turned Killer into some caricature, but he never gives into these lesser instincts. Instead, he approaches the role with tenderness and understanding, having a real fragility within him as he desperately stares at Natalie for help as he tries to piece together how to survive in a world that just tries to take advantage of him and that he does not quite understand. Though Caan would become a bigger star over the years and star in better films, his performance in The Rain People stands as one of the finest of his career, rich in subtlety and physicality that so often says more than words ever could. – Kevin Jones

Brian’s Song (1971)

In the early 1970s, ABC broadcasted a new film every week as part of their ABC Movie of the Week anthology series. The series aired for six years, a fine success for the network, and premiered a number of films that would stand the test of time including Steven Spielberg’s early film Duel and Buzz Kulik’s Brian’s Song starring James Caan and Billy Dee Williams.

Caan and Williams star as Chicago Bears football players Brian Piccolo and Gale Sayers, respectively. The film follows the NFL teammates beginning at the start of their careers, the two becoming the first interracial roommates in the history of the NFL. Through supporting each other, the two became starters for the Bears and played a single season on the field together in 1969. During the season however, Piccolo was diagnosed with cancer and rapidly succumbed to his illness. Brian’s Song portrays the camaraderie the two men built together as well as the challenging final days of Brian Piccolo. The film’s closing scene is hard to forget as Sayers says his final goodbye to Piccolo. James Caan portrays the pain that Piccolo is in as Piccolo struggles to get out words, and the scene is touching and saddening. James Caan and Billy Dee Williams excel in conveying the bond between the two men, and enable Brian’s Song to be a heartfelt homage to Piccolo and Sayers’ friendship. – Alex Sitaras

The Gambler (1974)

In one of his very best roles, James Caan starred as Axel Freed in director Karel Reisz’s The Gambler. A Dostoevsky-quoting English professor by day and a gambling addict by night, Axel’s life is spiraling out of control. Drawn in by risk, both in life and in gambling, it is perhaps more accurate that Axel is an adrenaline junkie whose only way to feel that rush is through gambling. As Axel will explain, he views life as the line in an e.e. cummings poem that simply reads, “Buffalo Bill’s defunct.” Chasing a high, taking risks, and living life on the edge, like an old-school cowboy is all Axel knows, even as he fatalistically understands he is building to his own demise.

Caan captures every self-destructive tendency coursing through Axel, all while possessing a wisdom and a general sense of control that brings a calmness to the film. It is not a particularly suspenseful or stressful film, in large part thanks to Caan’s laid back demeanor. Playing it as he does makes it feel as though Axel is somehow in control, even as things fall apart. He knows what he is doing, knows when he will stop, and nothing will stop him from seeing his fate. It is fascinating and frustrating simultaneously, a credit to Caan who so eloquently recites Dostoevsky before frantically racing to place a bet on Georgia Tech. Showing off his range, charisma, and depth, Caan brings Axel Freed to life in The Gambler. – Kevin Jones

Thief (1981)

When I think of my favorite pieces of acting in all of cinema, James Caan’s work in Thief always surfaces to the very top. In Michael Mann’s debut feature film, Caan stars as Frank, the quintessential Mann protagonist – a brooding professional of both sensitivity and violence, equal parts brutishness and elegance. Recently released from an eleven-year stint in prison for stealing forty dollars, Frank works as a car dealer and club owner by day, jewelry thief by night. When one of his scores is intercepted by the local Chicago mafia, Frank becomes entangled with one of their top leaders, Leo (Robert Prosky), who then sponsors his future thefts in exchange for a cut. The story of Thief, and the likable yet dangerous type of character it centers around, is nothing particularly new to crime cinema, but what elevates the film to masterpiece status is both Mann’s gorgeously dreamy, droning style, and Caan’s one-of-a-kind performance.

There is not a single moment in the film where Caan is not totally convincing as this fascinatingly flawed, broken character. From the riveting opening heist (in which he demonstrates his real skill at cracking safes that he learned for the film) to the film’s bloody, bitter conclusion, the actor carries Frank with a real lived-in, constantly on edge weariness. When he’s out in the world at his various day jobs, he walks around with the composed, proud posture of someone with something to prove to the world; when he’s cracking safes, his body language is anything but stiff or performative; instead, he comes across rather comfortable and natural, completely enraptured in the complexity and danger of the task at hand. 

Undoubtedly the most revealing moment for his character, however, is the film’s famous scene at a diner with his love interest played by Tuesday Weld. Frank reminisces to her the brutality and horror of his time in prison with both an emotional distance to the events and a blunt honesty, then shows her a magazine collage he has made of his life and the future he wishes to have with her. This scene is truly remarkable not only because of how well written and emotionally honest it is, but also because of how cogently Caan conveys the mindset of his character. Frank was “20 when he went in, 31 when he came out”, as he puts it himself, and Caan plays him exactly like a young man who has lost eleven years of his life to a cold, uncaring institution – somewhat naive and emotionally stunted in interpersonal relations, shrewd and calculating in his business. There is perhaps no single line that better encapsulates the type of cunning, professional loner he is than the one he utters during a meeting with Leo when his boss mockingly tells him that he should have joined a labor union if he wanted a greater say in his work’s profits. Pulling up his shirt to reveal the pistol he is brandishing under his belt, Caan retorts, “I am wearing it”. – Ben McDonald

Misery (1990)

One of best adaptations of Stephen King’s writing, Misery stars James Caan as novelist Paul Sheldon who is taken in by nurse Anne Wilkes (Kathy Bates) following Sheldon spiraling off of the road during a blizzard. “Taken in” is putting it lightly – tormented would be a better descriptor. Claiming to be one of Sheldon’s biggest fans, Wilkes has an obsessive knowledge of Sheldon and his novels. Promising to send Sheldon to a hospital once the roads are cleared, it becomes more and more evident as the days pass that she has no intent on doing so – Sheldon is to be her prisoner, handicapped by his accident and unable to fend for himself. Sheldon quickly discovers that Wilkes is unstable and poses a danger to his life, and he must devise a means to escape from his locked room. As a novelist, he has a few crafty ideas..

Thirty years later, Misery holds up. The horror in the film is jarring, and we can see in today’s horror a number of scares cut from the same cloth as Misery. Imprisonment is conducive to fear, and it is James Caan’s acting, specifically his growing sense of desperation opposite to a disturbed performance by Kathy Bates, that elevates the film to become unsettling. Confined to a bed and then a wheelchair, Sheldon is handicapped and forces Caan to act primarily through expression and belabored movement, convincingly conveying his character’s predicament. Although we suspect that Sheldon will escape his confinement (he has to, right?), James Caan is able to make this journey a worthwhile one.