The late James Gandolfini wasn’t always the hulking, balding man the world came to know as Tony Soprano. Long before he became the face of one of television’s most iconic antiheroes, he was a charming, popular teenager in New Jersey—voted both “best looking” and “biggest flirt” in high school—who had no idea how large a shadow his future career would cast.

Born on September 18, 1961, in Westwood, New Jersey, Gandolfini grew up in a working-class Italian American family. His father was the building maintenance chief at a Catholic school, and his mother worked as a high school lunch lady. Friends from those years remember him as a “happy, cute little boy” who carried himself with a quiet confidence that drew people in long before any casting director knew his name.

By the time he reached his senior year at Park Ridge High School in 1979, the young man—already standing over six feet tall—was one of the most popular students. He excelled in both academics and extracurricular activities and began to explore acting through the school’s theatre program. That was also around the time he crossed paths, indirectly, with another New Jersey star: John Travolta. Travolta later recalled that his father owned a tire shop Gandolfini’s father frequented. “My father sold tires to his father,” Travolta said after Gandolfini’s death. “I was his inspiration to get into the business… He would see pictures of me on the wall from movies and he decided that he wanted to be an actor.”

Before heading to Rutgers University, where he earned a Bachelor of Arts, Gandolfini’s classmates gave him a send-off that hinted at his natural magnetism. In their senior superlatives, they voted him “best looking” and “biggest flirt.” An old yearbook photo shared on social media later showed him alongside Donna Lange as the school’s “class flirts,” smiling widely for the camera. “I always remember him like this… happy kid with that killer smile,” one former classmate wrote. Another friend, Duff Lambros, recalled that he had “a quiet confidence” and “a cool dignity,” adding, “Girls loved him. Guys loved him. When he cracked that smile, it wasn’t just teeth, he smiled with his eyes. It felt like the sun was shining.”

That warmth and presence would become a hallmark of his work, but it was his role as Tony Soprano that would transform him into a global icon. As the deeply flawed Mafia boss and family patriarch in HBO’s The Sopranos, Gandolfini gave life to a character who could be sensitive and vulnerable in one moment, brutal and sociopathic in the next. His performance redefined what television drama could be and earned him multiple Emmy Awards, a Golden Globe, and widespread critical acclaim.

Speaking about the role to Vogue, he once joked, “I am playing an Italian lunatic from New Jersey, and that’s basically what I am.” Over six seasons, viewers watched Tony Soprano battle panic attacks, infidelity, rival mobsters, and his own conscience, leading up to the famously ambiguous final scene in 2007, when the screen cut to black and fans were left to debate whether Tony lived or died.

Away from the camera, Gandolfini’s life ended as abruptly as that final shot. On June 19, 2013, while traveling in Italy with his family, he suffered a heart attack and died in his hotel room in Rome at the age of 51. His 13-year-old son, Michael, was with him. Gandolfini left behind his wife, Deborah Lin—whom he married in 2008—their daughter Liliane, born in 2012, and Michael, his son from his first marriage to Marcy Wudarski.

Years later, Michael would carry his father’s legacy back to the screen, taking on the role of a young Tony Soprano in the 2021 prequel film The Many Saints of Newark. Reflecting on the experience, he told The New York Times that he initially focused on one thing: “I want to make my dad proud.” He admitted he hadn’t fully grasped his father’s cultural impact when he was growing up. “I truly wasn’t aware of the legacy of him… My dad was just my dad.” Still, the resemblance—in his eyes, expressions, and even the soft yet intense voice—reminded fans just how deeply Tony Soprano was intertwined with Gandolfini’s own presence. “The pressure is real,” he said. “Not only was it the feeling of my dad – it was like, Tony Soprano is a f***ing hard character.”

Despite the toughness of Tony, those who knew Gandolfini personally often describe him in very different terms: generous, humble, and deeply human. Travolta, who later starred with him in several films, remembered him not just as a powerhouse actor but as a profoundly decent man. “He was a people person first and then everything else,” Travolta said. “He was this beautiful man and I love him very much.”

For all of Tony Soprano’s imposing presence, Gandolfini often downplayed himself with humor. He once described himself as a “260-pound Woody Allen,” poking fun at his own anxieties and unassuming nature, even as he embodied one of the most intimidating figures in television history.

From the “biggest flirt” in a New Jersey high school yearbook to a performer whose work reshaped modern television, James Gandolfini left a legacy that stretches far beyond a single character. Fans remember him as Tony, critics hail him as one of the greats of his generation, and those who knew him personally recall a man whose warmth and humanity were as memorable as any role he played.