To celebrate Gandolfini's prolific career, we're looking back on the roles that made us laugh, weep, and freeze in terror. While usually a tough guy, Gandolfini also showed us a softer side, stood on both sides of the law, and even portrayed a giant furry creature.
Check out the acting genius's most memorable moments on the big screen.
Gallery | James Gandolfini's Most Memorable Movie Moments
- 'Romance & Cigarettes' (2005)
That’s right, Gandolfini was in a musical with Susan Sarandon, Kate Winslet, Steve Buscemi, Christopher Walken, Mandy Moore, and Eddie Izzard. In this clip, Gandolfini sings about the woes of love as he’s caught between troubles with his wife (Sarandon) and his lust for a lingerie salesgirl (Winslet). Sadly, we don’t get a taste of Gandolfini’s moves, but the rest of the townspeople dance and twirl around him. Pure gold.
- ‘Where the Wild Things Are’ (2009)
You probably had a hard time imagining the voice of Tony Soprano bringing one of the Wild Things to life in Spike Jonze’s adaptation of the classic children’s book. Yet Gandolfini brought deep warmth and compelling emotion to the giant, furry, angsty Carol. Who knew the tough guy could be so sentimental and cuddly?
- 'In the Loop' (2009)
Gandolfini showed his comedic side as anti-war General George Miller in this black comedy based on BBC series “The Thick of It.” In this hilarious scene, Gen. Miller sneaks away to a young girl’s empty bedroom to discuss war planning and uses a pink Cabbage Patch Kids-esque calculator to figure out his troop casualties. What better way to calculate your soldiers’ deaths than with a chipmunk-voiced talking calculator?
- 'True Romance' (1993)
Gandolfini played a scary badass like no other, but in "True Romance" one of his scary badass characters seriously underestimates a pissed-off girl. In the classic corkscrew fight scene from the Tony Scott film, Gandolfini’s Virgil surprises Arquette’s Alabama in her hotel room and proceeds to beat the crap out of her. Thinking a corkscrew can do little damage, he stupidly lets her fight back and ends up engulfed in flames (thanks to some hair spray) with a corkscrew in his foot, a toilet cover smashed against his head, and a couple shotgun blasts to the face. Gandolfini's mob man has messed with the wrong lady.
- 'The Last Castle' (2001)
In “The Last Castle” Gandolfini played Colonel Winter, the warden of a maximum security military prison whom no prisoners want to mess with. Robert Redford is a three-star Lieutenant who rallies the inmates to rebel against Winter. When Redford and Gandolfini butt heads, it’s definitely not pretty.
- 'The Mexican' (2001)
Gandolfini as a gay hitman; enough said. While “The Mexican” isn’t necessarily memorable (except for being not that great), it is for Gandolfini’s Leroy, who kidnaps Julia Roberts’s Samantha, girlfriend of a low-level gangster played by Brad Pitt. In this scene Samantha gets Leroy to cry as he talks about his romantic evening with a postman the night before. If this moment doesn’t prove Gandolfini’s true versatility as an actor, nothing does.
- 'Killing Them Softly' (2012)
Gandolfini teamed up with Pitt again to do what they do best: kill some guys. Gandolfini plays Mickey, a hit man with a serious alcohol problem -- and Pitt’s Jackie Coogan is having none of it.
- ‘Get Shorty’ (1995)
Usually no one would mess with a Gandolfini character, but in “Get Shorty” he ends up being a bit too soft to handle the big guys. His bodyguard Bear is too kindhearted for the crime world (he brings his daughter on business with him) and is no match for John Travolta’s Chili Palmer. When introduced as a part-time stuntman, Chili grabs poor Bear in the worst place imaginable and tosses him down the stairs. Bear is definitely no Soprano.
- '8MM' (1998)
In Joel Schumacher’s thriller “8MM,” Gandolfini played Eddie, a sleazy talent scout who gets caught for helping commit a murder on film years before. When called up by Nicholas Cage’s private investigator, Tom, and called out for his crime, Eddie gets pretty pissed and invokes a little Cage rage himself.
- 'Surviving Christmas' (2004)
The forgettable holiday comedy “Surviving Christmas” shouldn’t be on any Best Of lists, but this scene definitely deserves some remembering. Before we heard Gandolfini’s singing voice in “Romance & Cigarettes” we got a little taste in this scene when rich brat Draw (Ben Affleck) forces Gandolfini’s Tom to sing Christmas carols. What’s better than watching Tony Soprano struggle through “O Christmas Tree”?
- 'Welcome to the Rileys' (2010)
Gandolfini’s Doug Riley is a miserable, lost man looking for a sense of hope in all his sadness. After both his daughter and mistress die, Doug finds himself in a New Orleans strip club. He makes an offer to stripper Mallory (Kristen Stewart): He’ll pay her $100/day to live in her home, no sex, no nothing, just a place to stay. The usual tough-guy Gandolfini showed his real vulnerable core here.
- 'The Man Who Wasn’t There' (2001)
In this Coen Brothers’ film Gandolfini played Big Dave Brewster, boss of the department store where Dora (Frances McDormand) works who is always sharing his war stories. Big Dave gets blackmailed by Ed Crane (Billy Bob Thornton) into giving him money to start the new technology of dry cleaning.
- 'The Taking of Pelham 1 2 3' (2009)
Gandolfini played the New York City Mayor in Tony Scott's remake of the 1974 thriller. In this scene, reuniting Gandolfini and John Travolta, Travolta’s Ryder calls up the Mayor to demand ransom money while holding a subway train hostage.
- 'Lonely Hearts' (2006)
Gandolfini and Travolta teamed up on the other side of the law for "Lonely Hearts," in which the two played homicide detectives hunting down the real-life Lonely Hearts Killers, played by Jared Leto and Salma Hayek. It almost feels odd to watch these two trying to catch the bad guys rather than being them.
- 'She's So Lovely' (1997)
Gandolfini played a bit of an unexpected character in Nick Cassavetes’s “She’s So Lovely.” When he offers to buy the pregnant Maureen (Robin Wright Penn) a drink, things get a bit out of hand and the two get beyond wasted together. Gandolfini’s Kiefer attempts to rape her and then beats her. He is definitely one guy you don’t want to get a drink with.
- ‘The Incredible Burt Wonderstone’ (2013)
Although this failed attempt at comedy should remain forgotten, we still want to remember the last film role Gandolfini gave us before he passed. He plays Doug Munny, owner of Bally’s Casino where Burt (Steve Carell) and Anton (Steve Buscemi) perform. Apparently Gandolfini went to Vegas beforehand to prepare for his part by meeting famous magicians and the president of The Mirage. Gandolfini's Munny is a Vegas man if we’ve ever seen one.
- ‘Zero Dark Thirty’ (2012)
Gandolfini’s CIA Director in Kathryn Bigelow’s “Zero Dark Thirty” was, if anything, a strong role to leave us with. Portraying current Secretary of Defense and former CIA Director Leon Panetta, Gandolfini may have only been a supporting character, but he still left an impression that reminds us just how great of an actor he really was.
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