El Dorado (1966) Trailer

Caan was 25 years old when director Howard Hawks tapped him for a supporting role in El Dorado, a Western starring John Wayne and Robert Mitchum. His character, Alan Bourdillon Traherne, better known as Mississippi, is out for vengeance, a quest that catches the attention of Cole Thornton (Wayne) Sheriff Harrah (Mitchum). Thornton takes a liking to Mississippi, and they form a bond, though it’s not quite father-son. That’s made clear when Mississippi snaps, “I am NOT your son!” Caan more than holds his own with the veteran actors and there’s no better scene with Wayne than the dialogue-free moment when Mississippi helps a wounded Thornton onto his horse. It’s hard to distinguish whether that’s Mississippi respecting Thornton or Caan respecting Wayne. Maybe it’s both.

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3 / 16

Brian’s Song (1971)

Brian’s Song (1971)

Brian’s Song 1971 Trailer | James Caan | Billy Dee Williams

Brian’s Song is the single most heartbreaking entry in Caan’s filmography. The book was a tearjerker, and the TV movie is even more so. How could it not be as viewers watch grind-it-out NFL football player Brian Piccolo (Caan) succumb to the ravages of cancer despite the efforts of his best friend (Billy Dee Williams as superstar Gale Sayers), his wife (Shelley Fabares), and his coach (Jack Warden as George Halas). Caan imbues Piccolo with grace and humor, but also reveals his anger and desperation, which makes it hurt even more as he fades away. Caan and Williams, who shared palpable bromance chemistry, both earned Emmy nominations.

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4 / 16

The Godfather (1972)

The Godfather (1972)

THE GODFATHER | 50th Anniversary Trailer | Paramount Pictures

Even in a brilliant movie with brilliant performances across the board, Caan’s turn as Sonny Corleone stands out in Francis Ford Coppola’s The Godfather. Sonny is never, ever, ever going to become the next Don, and Caan drives home the reasons why. Hot-headed, a loose cannon, and too unpredictable for most of his own family, Sonny practically digs his own grave. Caan, without overacting the role, explodes at all the right moments, but even scarier are the scenes where Sonny simply stews and simmers, when the characters—and the audience—don’t know what he’ll do next. Caan, Robert Duvall, and Al Pacino were all Oscar-nominated in the Best Supporting Actor category and probably canceled each other out, as Joel Grey took home the statuette for Cabaret. But, make no mistake, Sonny Corleone was Caan’s defining role.

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5 / 16

Freebie And The Bean (1974)

Freebie And The Bean (1974)

Freebie and the Bean (1974) Official Trailer - Alan Arkin, James Caan Movie HD

James Caan in a comedy? After The Godfather, Cinderella Liberty, and The Gambler, Caan was ready for something lighter. Or was he? Freebie And The Bean was originally conceived as a drama and evolved into a comedy. Caan and Alan Arkin star as less-than-angelic San Francisco cops who must protect a witness in a case they’ve spent more than a year trying to close out. Every step of the way, Freebie and Bean are at each other’s throats (literally), wreaking havoc across San Fran in the process, as cars (lots of them) crash, guns are fired, and things go boom. Caan and Arkin are a great team, never better than when they’re finishing each other’s sentences, and there are several scenes in which Arkin appears to make Caan break character (with a smile or chuckle). Critics hated the film, but audiences loved it. And that sounds about right.

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6 / 16

Rollerball (1975)

Rollerball (1975)

Rollerball Official Trailer #1 - James Caan Movie (1975) HD

Rollerball was a modest hit that’s actually a lowkey dystopian classic. Directed by Norman Jewison, it stars Caan as Jonathan E, the aging icon who rules a brutal, violent game called Rollerball. Jonathan rejects a request/demand to throw a match from the head (John Houseman) of the powerful conglomerate that runs the league, setting up a final, to-the-death showdown. There’s precious little subtlety to much of the movie, but Caan—who was 35 at the time—brings heart and smarts to the situation. He’s also quite convincing on his skates and wielding the ball. Oh, and the film is set deep in the future … 2018.

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7 / 16

Thief (1981)

Thief (1981)

THIEF - Trailer - (1981) - HQ

We’re going to say it and we’ll die on this hill. Thief is Caan’s best film and it features his best performance. Caan, who’d just starred in and directed the imperfect but underrated Hide In Plain Sight, agreed to serve as the leading man for Michael Mann’s directorial debut. The film is sleek, dark neo noir with a pulsating score by Tangerine Dream. Caan plays Frank, a Chicago ex-con who wants it all: a thriving criminal enterprise and a happy family life—wife, kid, and all. Everything’s going to plan until Frank crosses paths with Leo (Robert Prosky), a take-no-prisoners mob boss. Caan beautifully captures Frank’s dilemma; it’s in his eyes, in the way he sweats, in the gentle moments (with Tuesday Weld), and in the funny buddy bits with a pal (a particularly effective Jim Belushi). And when Frank goes scorched earth, Caan has you rooting for him to burn everything the fuck down.

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8 / 16

Gardens Of Stone (1987)

Gardens Of Stone (1987)

Gardens of Stone Trailer 1987 (VHS Capture)

Caan reunited with Francis Coppola for Gardens of Stone, a Vietnam War drama that as a whole ranks as a well-intentioned misfire. It’s basically the anti-Apocalypse Now: understated, talky, straightforward. Caan plays a veteran named Hazard, who reluctantly leads the guards who patrol the Tomb of the Unknown Soldier at Arlington National Cemetery and serve as the honor guard for the funerals of soldiers lost in battle. Hazard interacts with several other characters, including his girlfriend (Anjelica Huston), a friend and superior officer (James Earl Jones), and kid (D.B. Sweeney) who’s itching to go fight in Vietnam. Caan shares chemistry with all three co-stars, especially Huston, and the movie’s final scene is emotionally compelling, but sadly, it’s good work lost in an okay movie.

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9 / 16

Alien Nation (1988)

Alien Nation (1988)

Alien Nation (1988) - Trailer

Truth be told, when most people think of Alien Nation, they’re likely thinking about the television adaptation, which was based on this thought-provoking film. Set in 1991, it explores what happens three years after formerly enslaved aliens—dubbed “Newcomers”—arrive on Earth and began to assimilate into the everyday life of Los Angeles. A human cop, Sykes (Caan), and a Newcomer cop, Sam Francisco (Mandy Patinkin), partner up to solve the murder of a Newcomer. It’s a reluctant buddy drama with a sci-fi twist, with Caan breathing life into a maverick character who’s alternately racist, understanding, cranky, impatient, and friendly as he slowly grows to respect and then befriend Francisco.

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10 / 16

Misery (1990)

Misery (1990)

Misery (1990) - Official Trailer

Misery runs 107 minutes, and Caan spends most of it confined to a bed, as his character, bestselling author Paul Sheldon, contends with unhinged fan Annie Wilkes (Kathy Bates). Bates won a Best Actress Oscar for her performance, and deservedly so, while Caan, who completes and complements her performance, didn’t even receive a Best Actor nomination. We get it, though. Bates has the flashier role, while Caan is called upon to simmer and stew and scheme, with occasional bursts of mostly verbal fury, and flashes of fake warmth. He pulls you in, even though Sheldon is a bit of a jerk. And just try not to scream in terror along with Sheldon when Annie takes a sledgehammer to his ankles.

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11 / 16

Honeymoon in Vegas (1992)

Honeymoon in Vegas (1992)

Honeymoon in Vegas Official Trailer #1 - Nicolas Cage Movie (1992) HD

Caan returns to comedy mode for Honeymoon In Vegas. Here, he’s Tommy, a likeable Las Vegas gambler who meets a school teacher, Betsy (Sarah Jessica Parker) and her boyfriend, a private investigator named Jack (Nicolas Cage). Jack loves Betsy, but promised his mother he’d never get married. Anyway, Jack loses a load of money to Tommy, who agrees to let him off the hook in exchange for a weekend in Hawaii with Betsy. She starts to fall for Tommy, while Jack grows ever more desperate. Caan breezes through most of the movie looking stylish and oozing charm (especially in his scenes with the effervescent Parker) … until a character shift that Caan can’t sell because it just feels so wrong.

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12 / 16

Bottle Rocket (1996)

Bottle Rocket (1996)

Bottle Rocket (1996) Trailer #1 | Movieclips Classic Trailers

Owen Wilson, Luke Wilson, and Robert Musgrave star as friends with lofty dreams of becoming crooks in Bottle Rocket, Wes Anderson’s feature directorial debut. But like bottle rockets, they’re far, far from serious explosives. The trio connect with Mr. Henry (Caan), a more established criminal who sees the humor in everything and uses a semi-legit gardening business, Lawn Wranglers, as a front for his operations. Caan, at the time, was the only “name” in the movie, and he lends it gravitas. Mr. Henry is a hero to the boys, and Caan delivers the character’s humor, tough love, and affection in equal measure. If Caan ever gave a sweet performance, this is it.

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13 / 16

The Way Of The Gun (2000)

The Way Of The Gun (2000)

The Way Of The Gun | Theatrical Trailer | 2000

Hot off his success writing The Usual Suspects, Christopher McQuarrie wrote and directed this convoluted and ultra-violent but engrossing thriller The Way Of The Gun. Benicio del Toro and Ryan Phillippe play criminals who see a big payday in kidnapping a woman (Juliette Lewis) who’s carrying a baby for an older man (Scott Wilson) and his much younger trophy wife (Kristin Lehman). Hmmm, bad idea. The older man turns to an old friend, Joe (Caan), who takes matters into his own hands. It’s nothing Caan hasn’t played before, but, really, no one does it better. Here, he puts a fresh spin on it, as Joe is generally soft-spoken and more of a working-class guy and less nattily attired than most of Caan’s cons. Try not to get chills when Caan intones, “I handle Mr. Chidduck’s laundry, things like you. I make unpleasant decisions for him, which he can’t and never will know. And … he sleeps very well.”

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14 / 16

Elf (2003)

Elf (2003)

Elf (2003) Official Trailer

The endlessly wonderful Elf needed a Scrooge character to really put it over the top. Enter Caan as Walter Hobbs, a grumpy book publisher who is shocked to learn that Buddy (Will Ferrell), the lunatic man-child running around New York City in an elf costume, is his birth child. Caan somehow manages to keep a straight face while Ferrell brings the craziness. Actually, his face contorts in spasms of bewilderment and exasperation, until Buddy’s pure, unabashed joy wins him over. You just know that there’s a softie under that tough exterior, and when Walter finally gives in, Caan does it with a relatable slow burn that makes it that much more powerful. And, while the Ferrell-Caan scenes are pivotal, his moments with Mary Steenburgen as Walter’s wife Emily and young Daniel Tay as his son Michael set the stage for Walter’s turnaround. It’s as if they, like Buddy, see something in Walter that he might not even see in himself. And that emanates from Caan.

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15 / 16

Cloudy With A Chance Of Meatballs (2009) / Cloudy With A Chance Of Meatballs 2 (2013)

Cloudy With A Chance Of Meatballs (2009) / Cloudy With A Chance Of Meatballs 2 (2013)

Cloudy With a Chance of Meatballs - Official Trailer #1

There’s more than a bit of Walter Hobbs in Caan’s Cloudy character, Tim Lockwood. Well, minus the meanness. Tim is the father of tinkerer and inventor extraordinaire Flint Lockwood (Bill Hader), who thinks big but tends to bungle things. Case in point, his latest contraption converts water into food, but it soon goes haywire and it starts raining hamburgers, strawberries, spaghetti, pancakes, and more. Can Flint save the day, get the girl (Anna Faris), and earn the respect and affection of his technophobic dad? Spoiler … of course, he can. And it’s fun to listen as Caan evolves the character, in just a handful of scenes, from doubting to proud. It’s more of the same in the sequel, though in the second go-round, Tim teams up to help his son—a transformation that Caan makes us believe for more reasons than the script says so.

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