James Gandolfini wasn’t widely recognized by most television viewers when he landed the part of Tony Soprano. However, if you were familiar with character actors in the mid-90s, he was already a name on your list. Prior to his breakthrough role, Gandolfini had left a lasting impact with several significant supporting roles on the big screen. For instance, he played the menacing Lt. Bobby Dougherty in the submarine thriller “Crimson Tide,” a detective briefly possessed by a demon in “Fallen,” and Geena Davis’s affectionate boyfriend in “Angie.” He also appeared as a burly henchman named Bear who was beaten up by John Travolta in “Get Shorty,” and most memorably, the mob thug who fought to the death with Patricia Arquette — and lost — in “True Romance.” When Gandolfini entered the waiting room of Dr. Melfi’s office during the pilot episode of “The Sopranos,” staring intently at a statue of a nude woman, it was evident that he had discovered the role that would fully utilize his abilities and unveil talents yet untapped.
In the recently published biography titled “Gandolfini: Jim, Tony, and the Life of a Legend” by Jason Bailey, who is a critic, film historian, and contributor for Vulture, we delve into the intricate journey that led the actor to the orbit of “Sopranos” creator David Chase. Given Gandolfini’s private nature, the book mainly focuses on his life from an external perspective. As he granted only two comprehensive solo interviews throughout his career (one of which was with me in my role as a TV critic for the Star-Ledger), it is intriguing to learn about him through the perspectives of those who later came to know him as a colleague and friend. Even before he achieved fame, Gandolfini was known for his unpredictable, impulsive, and at times enigmatic demeanor.
An Excerpt From ’Gandolfini: Jim, Tony, and the Life of a Legend’
During this time, the pilot script for “The Sopranos” was being circulated among different networks. Meanwhile, David Chase was in contention for a job on a CBS series focusing on Marg Helgenberger and the Witness Protection Program. To showcase his writing skills, he submitted the “Sopranos” pilot script as a sample. This caught the attention of James Gandolfini’s managers, Mark Armstrong and Nancy Sanders – it turned out that Helgenberger was also one of their clients. CBS rejected the Helgenberger pilot, but when news broke about HBO’s deal for “The Sopranos”, Sanders saw an opportunity for Gandolfini. As she puts it, “I read it again, and I went, ‘Oh my God, I think I have Tony Soprano’.
On Sunday evening, as I savored a dinner with my spouse and a bottle of wine, the phone rang. It was Jim, and he sounded vaguely familiar. Despite my current state of relaxation, I found myself intrigued by his proposal for a chat. However, I made it clear that due to the effects of the wine and the busy day ahead, I might not remember our conversation. I asked him to call me back the next morning and send me his video reel via VHS.
True to his word, Jim’s reel arrived the following morning through a messenger. By 11 am, I had given Sanders a ring, ready to discuss my thoughts. “Here’s the deal,” I began, “I think he’s exceptionally talented. However, there’s one issue that gives me pause: Is he menacing enough for the role?
David,” she chuckled, “if what you’re wondering about is whether he seems menacing enough… Well, if you described him as ‘a bit plump’ or ‘balding,’ I could get that. But he gives off a vibe of being genuinely threatening. This, it seems, is your man.
In the movie adaptation of “The Sopranos,” Chase mused about Robert De Niro, stating that no one else came close to being Tony Soprano for him after that. They enlisted casting directors Georgianne Walken and Sheila Jaffe due to their work on Steve Buscemi’s film “Trees Lounge.” At the time, they had little experience in television as they were primarily involved in independent films. In 1996, they assisted writer-director Melissa Painter in casting a project she was developing at Sundance Labs (later released as her 1999 film, “Wildflowers”). Painter recommended Gandolfini, whom she knew personally.
Jaffe stated, “Jim Gandolfini was always portraying tough characters in our eyes, but this role as a hippie father was quite distinct. I’ve admired his acting skills, having seen him in ‘A Streetcar Named Desire’ with Aida Turturro. He always seemed intriguing to me, yet I hadn’t witnessed him taking on such roles before. However, when this project came along, it was more like a trial, ‘Why not?’ he took up the challenge and delivered an outstanding performance. This experience revealed another facet of him that I believe the public hadn’t seen yet, showcasing his versatility as an actor, because Jim Gandolfini was indeed a wonderful person.
Gandolfini felt ecstatic about Chase’s “Sopranos” script, as Sanders, Walken, and Jaffe were advocating for him. He once remarked, “I remember saying something like, ‘I could kick this guy in the face, but I’ll never get cast.’ I thought they’d hire some good-looking actor instead.” He also expected HBO to choose one of the many Irish-looking actors who were popular on TV at the time. Interestingly, Gandolfini wasn’t the only contender for Tony, although Walken pointed out that the list of Italian candidates was long but not extremely so. Everyone had to audition first for Chase and then for HBO executives. Mark Armstrong recalled their argument: “We said HBO should already know who he is,” he stated. “After all, ABC, which was very influential back then, was offering him the lead in a show. So we said, ‘No, but we will arrange a meeting with David,'” and they set up a breakfast meeting.
In those days, I was quite young and often stayed out late. I remember thinking, ‘What a nuisance! This person wants breakfast. He’s going to be troublesome.’ So, we met and spent the majority of the time laughing about our moms and families.
Afterward, Gandolfini sat down with the decision-makers at HBO, and as Armstrong chuckles, he shared his willingness to read. “Considering all of us urging him that he didn’t need to,” Armstrong added. In Jim’s own words, “I was destined to play Tony… I wanted it so fiercely that I agreed to audition for the role.
Walken and Jaffe hired an audition space on 72nd Street, added a table and some chairs, then positioned a camera. Jim arrived, conversed with Chase momentarily, and commenced reading. “He was quite competent,” Chase remarked. However, Jim barely scratched the surface before halting his reading and started expressing remorse. “I’m not doing this correctly,” he asserted. “I didn’t prepare for this properly. I’m messing it up. And I don’t wish to continue. I want to return and do it again for you.
Chase remembered him saying he’d return the next Friday. However, when Friday arrived, he couldn’t make it, as they were informed: His mother had unfortunately passed away. It turned out to be a ruse; Santa Gandolfini had already deceased several months prior.
When Jim decided it was time to come back, Chase had already returned to Los Angeles. However, Walken and Jaffe were keen on him, as they had always favored the idea – “He was our preferred concept from the start,” Jaffe admitted. So, they arranged for him to fly out to Los Angeles to record his audition. “David operated the camera, while I read,” Jaffe recalled. “And it was recorded on VHS tapes. That’s how far back it was. Afterward, David and I rushed to his house, watched the recording, and we both got quite excited.

In his words, “Once he thoroughly prepared and went over the script, it became crystal clear,” Chase stated. “There wasn’t even a hint of doubt. He was the perfect choice.” However, Chase wanted to be absolutely sure. “The casting process involved numerous auditions – many contenders vied for that role,” he explained. “In fact, they prefer to consider multiple options. So, three actors were called in by HBO for the part of Tony, and Jim was one of them.
In relation to what Michael Imperioli mentioned, there were three individuals trying out for the character Tony, with him being present at the network audition for another role. Among them were Jim Gandolfini, whom he didn’t know; Mike Rispoli, his friend who later played Giacomo Michael ‘Jackie’ Aprile Sr.; and a third person who looked familiar but he couldn’t identify. However, the casting director pointed out that the unrecognizable individual was actually Little Steven Van Zandt wearing a wig.
In the room, there wasn’t an instant agreement. To Susie Fitzgerald, who represented management-production company Brillstein-Grey, “the moment he entered the room, I thought, That’s definitely him.” However, Chase required some persuasion, as Fitzgerald described. Chase was a fan of Stevie Van Zandt. Fitzgerald strongly advocated for Gandolfini; she remembered Chase expressing concerns about Gandolfini’s on-set behavior, stating “He can be a handful on set.
“I don’t care about that,” she replied. “Is it him?”
As stated by Chris Albrecht, President of HBO Original Programming, “Rispoli was exceptional. He was funnier than Jimmy due to his natural flow. We discussed this, and David explained, ‘The show I imagined is the one with Jimmy in it. It’s a significantly different show if you replace Jimmy with Rispoli, but the show I envisioned is darker with Jimmy. It’s a more authentic show with Jimmy.’ After a brief pause, we decided to cast Jimmy.”
Chris Albrecht, HBO’s President of Original Programming, said that Rispoli was really good and funnier because of his natural style. They talked about it, and David (the creator of the show) said the show would be very different if Rispoli or Jimmy were in it, but the show he envisioned is the one with Jimmy. It’s a darker show with Jimmy, and they decided to cast him because it felt more real. In television, ‘dark’ isn’t usually what you aim for, but this time, ‘real’ was the choice.
Among all, the actor himself was taken aback the most. “It was an extraordinary act of trust,” he confessed. “To be honest, it wasn’t a group of stylish ladies in Manhattan [like in Sex and the City]. This was a band of larger men from New Jersey.” In private moments, he harbored doubts about the series and his part in it. Nancy Sanders recalls having dinner with Jim and his agent, David Brownstein, at a restaurant near HBO’s headquarters, where they tried to persuade him to sign the contract and navigated through an eleventh-hour wave of self-doubt.
He questioned, ‘What’s the reason for this?’ She replied, “Initially, I approached you for film roles. Now, I’m working on an HBO series? I’m not familiar with that network at all!
She responded, “Jim, give me your attention.” She declared, “This is the finest written work I’ve encountered, whether on screen (TV or film) or stage (theater). Let me assure you: It’s worth investing in. While it may not revolutionize the world, it will certainly transform TV.
He let out a sigh, muttering, ‘Well, that’s just great.’ He then went ahead and signed the documents. Upon informing director Roberto Monticello of this news, James Gandolfini lamented, ‘Oh my God, Roberto, it seems I’ll be jobless in less than a year. Who on earth would watch a TV series about Jersey mobsters?’
By Jason Bailey: Exploring the Life of Legendary Actor James Gandolfini – “Jim, Tony, and the Life of a Legend” (Published by Abrams Press), available for purchase from April 29, 2025. Copyright © 2025 Jason Bailey.

Gandolfini: Jim, Tony, and the Life of a Legend by Jason Bailey
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2025-04-25 14:55