It is, of course, his eyes that get you first, his eyes that give him away.

You walk into the restaurant, scan the room, and there he is, hunched over a table tucked close to the wall, catching your eyes with his. Eyes exactly like his father’s. He pops up from his seat, extends his hand, and gives a big smile—the same smile his father had but rarely flashed. “Hi, I’m Michael Gandolfini,” he says. He’s thinner than his father was, and full of boyish energy. But you notice other mannerisms—the way he runs his fingers through his hair, how he rubs his nose with the back of his hand. And all at once you realize why it was inevitable that David Chase would cast him, the twenty-year-old son of the man who played the adult Tony Soprano, James Gandolfini, as the teenage Tony in the feature-length Sopranos prequel, The Many Saints of Newark (2020).

“He wanted me to play sports. I felt that burden. I wanted to make him proud."



Suit and turtleneck sweater by Dior Men; gold ring and gold-and-carbon ring by David Yurman. Marco Grob

Stepping into your father’s shoes would be fraught for any of us. Your identity becomes forever entwined with his. Now imagine you are not just pursuing your father’s profession, seeking your own path, but you are also taking on the role he made iconic. So here you are, playing the younger version of a man your father brought to life, and yet your father, the man who created this role—as well as you, his son—is gone. Has been since you were fourteen years old. You were there when he died of a heart attack, in June 2013, while on a family vacation in Rome. He was just fifty-one.

Michael, just shy of his fourth birthday, sits on James’s shoulders, in 2004. Getty

“Yeah, it was a difficult decision,” Michael says when I ask him about assuming the role. He was born in 1999, the year The Sopranos debuted. He liked performing; as a kid, he saw Wicked and loved it. “I dressed up as the Scarecrow almost every night, and my dad would videotape me singing,” he says. But James discouraged his son from making it his career. “As I got older,” Michael says, “he wanted me to play sports. I felt that burden. I wanted to make him proud. And he said, ‘Don’t be an actor; be a director. They have the power.’ ”

It was his father’s death, however, that propelled Michael toward acting, after a friend suggested that acting classes might help him heal. Though he had second thoughts the night before he began, he says, “from the first day, I fell in love with it. It actually started my grieving process with my dad.” He gave up the football team for the drama club. He even starred as the title character in a local production of Shrek the Musical.

"As an actor, I had to watch this guy who created the role, to look for mannerisms, voice, all those things I would have to echo. But then I’d also be seeing my father."



Jacket and shirt by Gucci. Marco Grob

After high school, he enrolled at NYU, where he’s currently a sophomore. He got a manager and started to audition in New York. He landed the first role he tried out for: Joey Dwyer on HBO’s The Deuce, George Pelecanos and David Simon’s ode to the porno­copia of 1970s New York (returning for its third and final season on September 9). “When I got the role,” Michael says, “my manager joked, ‘You should quit acting now—you’re one-for-one.’ ”

Gandolfini as Joey Dwyer on Season 3 of HBO's The Deuce Courtesy

Then came the call from David Chase’s office. Chase was getting ready to make a movie about Tony Soprano’s early years.



“The funny thing is, before the audition, I had never watched a minute of The Sopranos. I was just a kid when he was making it. I would go to the set and ask him what it was about, and he’d say, ‘Oh, it’s about this guy who’s in the mob and kind of goes to therapy.’ The hardest part of this whole process was watching the show for the first time.” Michael pauses. “It was an intense process. Because, as an actor, I had to watch this guy who created the role, to look for mannerisms, voice, all those things I would have to echo. But then I’d also be seeing my father. I think what made it so hard was I had to do it alone. I was just sitting alone in my dark apartment, watching my dad all the time. I started having crazy dreams. I had one where I auditioned for David and I looked down at my hands, and they were my dad’s hands.”

"When he yells at A. J., and he gets a pizza to apologize, and he sits by his son’s bed and says, ‘I couldn’t ask for a better son.’ I just knew he was talking to me in that scene.”



Jacket, shirt, and trousers by The Row; Boots by Dior Homme. Marco Grob

I tell him that his father, as Tony, brought about so many indelible moments. Are there any that resonate with him? He describes two. “There’s a scene where Meadow comes home late at night, and he’s sitting with a drink, and he’s like, ‘You know I love you, right?’ That hit hard,” Michael says. “The other one that crushed me was when he yells at A. J., and he gets a pizza to apologize, and he sits by his son’s bed and says, ‘I couldn’t ask for a better son.’ I just knew he was talking to me in that scene.”



I ask him if he has anything from his father that he holds dear, any object. He tells me that when he was young, his father gave him a plaque. “He was away a lot, filming. It was a rough time. A lot of craziness going on. I was eight or nine. The plaque says, to michael, the boy with the heart of a lion.”

Just then the waiter comes. We settle up. What happens next for this Gandolfini?

Smash cut to black.



Marc Hom

This article appears in the September 2019 issue of Esquire

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Photographs by Marco Grob. Edited by Eric Sullivan. Styling by Alfonso Fernandez Navas.