James Gandolfini was one of the most gifted actors of his generation. Catching a glimpse of what the man was capable of throughout most of the 90s, his rise to superstardom was a slow but curtain. Quiet and reserved, Gandolfini's large stature and intimidating presence was nothing like his lovable, soft-spoken personality.

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Leaving us far too soon, James passed away in 2013 as he finally began to exit the looming shadow cast by the role that changed his life forever. A surprisingly versatile actor with a deceptive range, Gandolfini managed to capture our hearts and imagination in the short time he was on this planet. But of all the roles James Gandolfini chose, which were his most definitive?

9 Virgil ('True Romance')

The first time we set our eyes on Gandolfini was as the intimidating mob assassin, Virgil, in the Quentin Tarantino penned, True Romance. In the film, Virgil heads to Los Angeles to retrieve his bosses stolen cocaine. Brutal and violent, Gandolfini's portrayal of the killer was not only sadistic, but gave moviegoers one of the coolest fight scenes in cinema history, finally meeting a fittingly brutal end. Virgil was the first, but not the last, of Gandolfini's foray as gritty crime figures.

8 Winston Baldry ('The Mexican')

The Mexican was an 2001 action comedy starring Brad Pitt and Julia Roberts. When we first set eyes on Gandolfini as Winston Baldry aka Leroy, we expect a hard-nosed gangster something akin to Virgil or a curtain New Jersey crime boss, but that's not quite the case with Winston. Gandolfini's portrayal of a hired gun (not unlike Virgil), is more nuanced, charming and less sadistic. Winston is also a gay man, but that doesn't define his character, which Gandolfini pulls off effortlessly. As always, James manages to have instant chemistry with his female co-star (Julia Roberts) and the most enjoyable scenes of the film are when the pair shares the screen.

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7 Colonel Ed Winter ('The Last Castle')

Gandolfini's portrayal of a Colonel Winter was a welcomed change of pace, as viewers had become accustom to seeing the actor as nasty lawbreakers. However, Winter is every bit as sadistic as the other colorful cast of characters Gandolfini his played in the past, simply using his position within the military to justify his actions. Also, going nose to nose with Robert Redford is no small feet, but Gandolfini more than holds his own when sharing the screen with the Hollywood icon.

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6 Nick Murder ('Romance And Cigarettes')

James Gandolfini in a musical sounds like the opening to a joke, but in 2005 the actor flexed his comedic muscle and starred in the musical rom-com Romance and Cigarettes. Gandolfini fronts an all-star cast, in a story about a husband dipping his toes in the world of adulterous escapades must ultimately choose between his lover and his wife. Gandolfini’s portrayal of the scandalous, indulgent Mr. Murder mirrors his most memorable role, but contrasts with a healthy dash of comedy. Unfortunately, Nick ends up passing similarly to how Jim passed, being slightly eerie if not prophetic.

5 Charley Malloy ('On The Waterfront')

On the Waterfront was not well received to put it lightly. Plagued with script problems and other issues, the Broadway play would also see the firing of Gandolfini, something that would seem unthinkable later in his career. Despite the setbacks, Gandolfini ushered in an admirable effort in the short time with the production. A peek into what the actor was capable of, Gandolfini would take what he'd learned from that experience and venture away from the stage, eventually breaking into Hollywood.

4 CIA Director Leon Panetta ('Zero Dark Thirty')

Marking the first time the actor has portrayed an actual person, appearing as former CIA Director, Leon Panetta, Gandolfini brings an anxious, realness to the part while attempting to stay true to the real-life counterpart. Always his own worst critic, the actor convinced himself that Panetta would not be happy with the portrayal, stating, “I sent a note to Leon saying, ‘I'm sorry about everything. The wig, everything. You’re kind of like my father. You'll find something to be angry about.”

3 Carol ('Where The Wild Things Are')

The world has become accustom to seeing James Gandolfini on the screen. His distinctive profile is an image that his fans are all too familiar with, and the actor often uses his eyes as well as his body to tell a story. Showing a side not often seen, Gandolfini utilizes his voice alone to bring Carol, the lovable monster, to life in the Spike Jonez film. Though we do catch glimpses of classic Gandolfini anger, the actor manages to capture your imagination with his portrayal of the heart-warming monster.

2 Tony Soprano ('The Sopranos')

About as deplorable as a character can get, Anthony Soprano is a sociopathic gluten that committed adultery and a plethora of other heinous acts. So, why is it that millions of devoted fans adored this crime boss? Because of James Gandolfini. Gandolfini brought a visceral feel to the New Jersey crime boss, along with an undeniable charm and charisma that made it almost impossible to not like or even route for him. His quickness to anger, family issues and unintentional funny quotes grounded the otherwise grandiose character and made fans fall in love with the role that made Gandolfini a household name.

1 Albert ('Enough Said')

Though Tony Soprano was without a doubt Gandolfini's most iconic role, it was his portrayal of the warm and lovable Albert that showcased how versatile the actor really was. A complete contrast to the list of no-nonsense gangsters and bad egg that he has played in the past, Gandolfini showed audiences his soft, romantic side as the divorced father alongside Julia Louis-Dreyfus. Sadly, this was to be Gandolfini's final onscreen appearance, as the actor would pass away a year after completing the film.

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