The Best James Gandolfini Movies You May Never Have Seen

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Paramount Pictures/DreamWorks

The late, great James Gandolfini will always be remembered as Tony Soprano -- and it’s unquestionably his best role -- but he was also one of the best character actors in movies. After he exploded on the scene with ‘The Sopranos’ he was asked to do meatier roles in films, but as a television star transitioning into cinema, he often made films that weren’t big hits or didn’t attract much attention. So it’s worth pointing out five roles he had in films that you may have missed, especially if you’re looking for something to watch in memorial.

  • 1

    'The Mexican'

    (2001)
    Dreamworks

    ‘The Mexican’ looked like a blockbuster. It had Brad Pitt starring with Julia Roberts, and it was Gandolfini’s first big role after the success of ‘The Sopranos.’ Perhaps the weight of anticipation caused the film to mostly disappoint (yet, it’s the most successful film on the list), being rejected critically as a Quentin Tarantino knock off. Gandolfini plays Winston Baldry, the hitman with a soft spot for love who is meant to kidnap Roberts, but ends up forming a friendship with her. On the page, the character could have been too cutesy (he’s homosexual and is having relationship problems), but Gandolfini fills the character with believable pathos, and though -- much like Tony Soprano -- he’s a remorseless killer, Gandolfini shows how fragile the character is in a way that makes him empathetic, and maybe even a little tragic.

  • 2

    'The Man Who Wasn't There'

    (2001)
    Universal

    Another film that tried to trade on James Gandolfini’s newfound fame was Joel and Ethan Coen’s ‘The Man Who Wasn’t There.’ Shot in black and white, James played Big Dave Brewster, who ran the local department store looking to add an additional building. He’s also sleeping with the wife of the protagonist Ed Crane (played by Billy Bob Thorton), which leads to a blackmail threat. Besides slipping him into a noir setting – which fit him like a glove – Gandolfini got to play someone totally removed from Tony Soprano, a slightly weak and bloviating middle-management type who married into wealth and power. And, of course, he got to do it in a Coen Brothers film.

  • 3

    'In the Loop'

    (2009)
    IFC films

    Though ‘The Sopranos’ was at times hilarious, and Gandolfini showed us he knew how to make a joke, he made few actual comedies. ‘Veep’ creator Armando Iannucci’s ‘In the Loop’ showed that not only was Gandolfini great with the written word (as should be no surprise, he started on the stage), but he knew how to be funny. Part of a bigger ensemble, he only gets a few scenes in the movie, but it’s worth pointing out his range in a career that often had him play thugs.

  • 4

    'Killing Them Softly'

    (2012)
    The Weinstein Company

    Gandolfini always looked like a big bear on screen. Loveable maybe, but in ‘Killing Them Softly’ director Andrew Dominik makes him look cartoonishly sizable. His character is a drunk and when having drinks with Brad Pitt’s character, he picks up a beer glass and finishes it in one go. Whether the glass was made smaller for Gandolfini, or he was just that big a guy is hard to say, but it’s a great cinematic moment. Here he plays Mickey, who is sent to help Pitt’s Jackie Cogan but instead spends the weekend getting drunk, doing drugs, and sleeping with prostitutes. Mickey is pathetic, and though Gandolfini usually projects strength, here, he’s not afraid to show himself as someone who knows that the world has passed him by, and is probably better off spending the rest of his life behind bars. Whether he’s consciously or unconsciously having a last hurrah is left to the audience.

  • 5

    'Not Fade Away'

    (2012)
    Paramount Vantage

    With Gandolfini’s passing, this is the hardest film to write about. ‘Not Fade Away’ was David Chase’s first movie as a director, and – perhaps as a good luck charm – he brought in Gandolfini to work with again. In the film, set in the 60s, Gandolfini plays Pat, the father to main character. Pat doesn’t like that his son is being swept up with the changes of the time, but regardless of how he feels about his son's hippie clothing, Pat’s got cancer and he knows that his son will shortly become the man of the household. Though the movie never shows Gandolfini die -- much like in ‘The Sopranos’ -- his death is a fait accompli.  And that changes and softens his outlook on his child, and the two have a memorable dinner together where Gandolfini tries to communicate some things to his son, maybe most importantly, that he’s just a man. It’s beautifully nuanced work, and Gandolfini nails it.

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