The 13 best roles of James Caan's career

The best of James Caan

James Caan in Elf, The Godfather and Thief — Everett Collection (2); CBS via Getty Images

An iconoclast who defied his leading-man good looks and channeled them into something more interesting and enigmatic, James Caan (known affectionately as Jimmy to his friends) was a rare breed of actor who delighted in upending expectations. Nominated for an Oscar, an Emmy, and four Golden Globes, Caan was a new type of actor birthed out of the cynicism of the "New Hollywood" during the 1970s. An often combustible presence, he held deep respect and affection for his craft alongside a healthy degree of skepticism. His career spanned six decades, and he was still actively working at the time of his death on July 6, 2022. Here are James Caan's 13 best roles.

02 of 14

Lady in a Cage (1964)

James Caan Best Roles — Everett Collection

Caan began his career on the stage, transitioning to small roles on television before landing his first major film role in this Grand Guignol thriller starring Golden Age legend Olivia de Havilland. Caan plays Randall O'Connell, a hoodlum who sets to ransacking the home of wealthy widow Cornelia (de Havilland) after she gets trapped in her private elevator. De Havilland praised Caan's performance and called the experience of working with him "wonderful," earning him a vote of confidence from one of Hollywood's most beloved actresses.

03 of 14

Brian's Song (1971)

Best Sports TV and Movies — Everett Collection

Caan earned his only Emmy nomination for this TV movie, a true story about Chicago Bears football player Brian Piccolo (Caan), stricken with terminal cancer after finally turning pro. An ABC Movie of the Week, it chronicles Piccolo's friendship with teammate Gale Sayers (Billy Dee Williams) as the first interracial roommates in the history of the NFL. The athletic Caan had to actively be told to slow down while filming football scenes with Williams, whose character was renowned for his speed on the field. But it's Caan's dramatic acting that really shines, catapulting the project to such success, it vaulted from the small screen to a theatrical release. It's still one of the most dependable movies for making men cry.

04 of 14

The Godfather (1972)

Caan immortalized himself in what would become his signature role as lovable hothead Santino "Sonny" Corleone in Francis Ford Coppola's Mafia epic. Originally cast as Michael, Caan wanted the part of Sonny more, and Coppola fought to move him into the role, casting Al Pacino as the younger brother. Over 50 years of the film's history, Caan's Sonny — a blend of raw sex appeal, nervy impulsiveness, and deep empathy— has remained a fan favorite. He earned a Best Supporting Actor Oscar nomination for his work. For many, he remains the emotional heart of the original film, Sonny's short-fused temperament contrasting with Michael's cold descent into nihilism. And if you aren't yelling for Sonny not to get in that car every single viewing, you're not really watching.

05 of 14

The Gambler (1974)

Based on a semi-autobiographical screenplay by James Toback, The Gambler exemplified the offbeat choices Caan made after The Godfather turned him into a fully-fledged movie star. He stars as college English professor Axel Freed, who is struggling with a spiraling gambling addiction. Battling his own addiction to cocaine while making the film, Caan relished the role and the challenge of making us root for a man who steals from his own mother. Earning a Golden Globe nomination for his performance, the actor long called the film a personal favorite.

06 of 14

Funny Lady (1975)

While Caan made a great success of playing gangsters and hard-scrabble characters, he had immense range, as demonstrated by his turn in Funny Lady, a sequel to the 1968 musical Funny Girl. Starring opposite Barbra Streisand, who reprises her Oscar-winning role as Fanny Brice, Caan plays songwriter and musical impresario Billy Rose, Brice's husband. Caan even sings on the soundtrack, which was certified gold. While the film was considered a lesser effort than Funny Girl, Caan received strong notices for his performance, earning another Golden Globe nomination.

07 of 14

Rollerball (1975)

Part of the beloved wave of 1970s apocalyptic sci-fi thrillers, Rollerball is renowned director Norman Jewison's commentary on corporate feudalism and contact sports. Caan stars as Jonathan E., captain and star of Houston's rollerball team (a violent fictional sport). When Jonathan refuses to retire at the behest of the team sponsor, he finds himself enmeshed in a life-or-death game on the rink. A deeper movie than any photo will suggest (this one included), Rollerball is one of Caan's most visceral performances; the film is a serious comment about homegrown fascism and audience bloodlust.

08 of 14

Comes a Horseman (1978)

Were you really a movie star in the 1970s if you didn't make a movie with Alan J. Pakula? The master of such paranoia thrillers as Klute and All the President's Men, director Pakula departed from the formula for this 1940s-set Western. Caan stars as WWII veteran Frank Athearn, who tends a small plot of land, attempting to make a living ranching. When he and fellow rancher Ella (Jane Fonda) are threatened by land baron Jacob W. Ewing (Jason Robards), they find themselves in a fight for their livelihood — and their lives. It's a smaller role than usual for Caan, but it paired him with two other icons of the decade.

09 of 14

Thief (1981)

THIEF, James Caan (front), Willie Nelson, 1981, © United Artists/courtesy Everett Collection — Everett Collection

Not a box-office success on release, Thief has only grown in stature over the years. Marking writer-director Michael Mann's feature film debut, the movie stars Caan as Frank, a professional safecracker trying to work one last job before he goes straight and makes a life with the woman he loves, Jessie (Tuesday Weld). The moody, evocative cinematography and pervading sense of danger became hallmarks of Mann's work and remain highly influential on generations of filmmakers who've come after. Caan's laconic, emotionally stunted Frank is one of the most remarkably coiled performances of his career, and he often cited it alongside The Godfather as the film of which he was proudest. Nowhere is the magic of his acting on better display than in a lengthy monologue in a diner opposite Weld, where Caan's Frank recounts the physical and emotional toll of surviving prison, the walls of his restraint falling for just a moment.

10 of 14

Dick Tracy (1990)

Caan didn't make any films from 1982 to 1987, taking a self-imposed exile from Hollywood while he dealt with depression, cocaine addiction, and burnout. His initial return to acting featured a string of lackluster projects, but he did get to chew the scenery briefly under heaps of prosthetic make-up in Warren Beatty's Dick Tracy. A gonzo comic-book adaptation, the film polarizes critics, but Caan has fun as crime boss Spud Spaldoni, a semi-send-up of his star-making performance in The Godfather.

11 of 14

Misery (1990)

MiseryJames Caan — Merrick Morton/Columbia Pictures

Caan's true return to form came via this psychological thriller based on a Stephen King novel of the same name and directed by Rob Reiner. He stars as famous novelist Paul Sheldon, a romance author who is held hostage by his "No. 1 fan" Annie Wilkes (Kathy Bates) after a car accident. Caan was offered the role after numerous stars, including Kevin Kline, Harrison Ford, Robert Redford, and Dustin Hoffman, turned it down because the character is bedridden for much of the running time. But he relished the challenge, particularly the opportunity to take on a more reactive part opposite Bates' pathological Annie. Though Bates got all the Oscar love, Misery helped restore Caan to prominence — and the "hobbling" scene remains one of the scariest moments in movie history.

12 of 14

Bottle Rocket (1996)

Now one of the most revered directors of our time, Wes Anderson made his directorial debut with this crime comedy, buoyed by Caan's status as the only real star in the cast. Caan traded on his on-screen iconography as a gangster as Mr. Henry, a landscaper and part-time criminal idolized by aspiring thieves Dignan (Owen Wilson) and Anthony (Luke Wilson). Caan's wry sense of humor and deadpan delivery proved a perfect fit for Anderson's budding style. The film was not a success when it was released, but as the director's reputation has grown, it's become a classic of the heist genre.

13 of 14

Elf (2003)

5884647k — Alan Markfield/New Line Prods./Kobal/REX/Shutterstock

The actor endeared himself to a new generation of fans — and secured a place among the rarefied air of Christmas classics — with his role as Walter Hobbs, a workaholic book publisher and biological father to Buddy the Elf (Will Ferrell). While Ferrell's antics provide the film's indelible humor, it's Caan, once again, who lends the film its heart. His gruff, humorless Walter is the film's Scrooge, transformed by the magic of Christmas and Buddy's childlike wonder. Off-screen, Caan was known for his love of pranks and a persistent twinkle in his eye, and Elf let some of that seep through. His steady presence is the perfect foil for Ferrell's off-the-wall Buddy, and we dare you not to feel the Christmas cheer when Walter finally busts out into "Santa Claus is Coming to Town" at the film's climax.

14 of 14

Las Vegas (2003-2007)

Though Caan was working up to his death (and there are still some projects to come posthumously), one of his last standout roles came playing Ed Deline, the head of security and surveillance for the fictional Montecito casino. Caan channeled his tough-guy persona into the portrayal of this ex-CIA operative with a penchant for violence when necessary. According to his co-stars, Caan was instrumental in the show's writing and the depth of his character, regularly pushing for more complexity and humor in scripts. Though he eventually left the show to focus on making films, it marked his most successful TV venture.