James Gandolfini Stole the Show in This Underrated Gangster Film, 5 Years After ‘The Sopranos’

When James Gandolfini ended his star-making turn as Tony Soprano in HBO’s The Sopranos in 2007, it freed him up to pursue a film career that would allow the gifted actor to showcase many talents. He would go on to play characters that were nothing like the intimidating mafioso, but his role as Mickey in Killing Them Softly is as close as he would come to replicating the Emmy award-winning role.

Director Andrew Dominik gathered some of our favorite gangsters from across both film and television to round out a stellar ensemble cast. With Brad Pitt leading, Dominik surrounded him with performers known for their mob moxie, like Gandolfini, his Sopranos co-star Vincent Curatola, who played Johnny Sacks, and Ray Liotta (Henry Hill in Goodfellas). Despite his limited screen time, Gandolfini steals the show in just two scenes.

James Gandolfini Is a Cynical, Broken Hitman in ‘Killing Them Softly’

The first time the audience sees Gandolfini’s Mickey is at the airport, as he trudges away from the baggage claim to head to a meeting with Jackie Cogan (Pitt). He is dressed in a plain blazer and slacks and looks like any average businessman. But as Jackie sits with him at the bar, he quickly discovers that Mickey isn’t the same first-rate hitman that he wanted for the job. Mickey is in the process of getting divorced and has taken a liking to booze – lots of it. Jackie wants him to handle the whacking of one of the two men responsible for robbing a backroom poker game crawling with mobsters.

Gandolfini brings a similar hubris and Italian flair to the role, but inside, he is very different from Tony Soprano. After mowing through several martinis, Jackie notices his colleague hitting the drinks quickly and often. Gandolfini lets loose with his inhibitions, and his state of mind is of more significant concern. Tony’s bravado is there, but underneath it is a husk of a man broken and jaded by his failed marriage and thankless line of work. It’s a treat to see the vulnerable side of this giant of a man and how he has checked out emotionally.

A Second Meeting Between Mickey and Jackie Goes Even Worse

Jackie is already on the fence about bringing the now-raging alcoholic on board for this two-man job. Still, by the time he gets to Mickey’s hotel room, he discovers that his one-time mentor is also into a lascivious lifestyle that includes dalliances with multiple sex workers. There is a swagger that Gandolfini has that has always underlined his performances, and this role is no different, but there is an undeniable sadness that hangs over his character, as well.

In just two scenes and less than 15 minutes of screen time, Gandolfini elicits more emotional reactions from the viewer than any other accomplished movie performer. What makes his turn in Killing Them Softly even more impressive is that we never see what Mickey was like before we see the man who has given up on his life. We only get the “after” and no “before” from which to gauge how far his character has come off the rails. Great actors don’t necessarily need juxtaposition to enhance the flavor of a role. Just a year after this highly engaging performance, Gandolfini passed away in Rome, Italy. We would have loved to have seen what else the talented actor would have brought to the screen, but his legacy is forever ensconced in Hollywood lore.