Tony Soprano walked so that Walter White, and many more empathetic antiheroes, could run. Unfortunately for James Gandolfini, the actor who brought The Sopranos’ stone-cold sociopath to life, the line between fact and fiction became alarmingly blurry.
1. He Was A Working-Class Hero With A Dark Side
James Gandolfini was really good at playing bad guys on the big and small screen—perhaps even dangerously good. This New Jersey-born, Italian-American son of a custodian and a lunch lady shot to superstardom in the early 2000s while bringing the entire genre of prestige TV with him. Unfortunately, this much-loved actor was fame-averse and tormented by his many, many demons.
Featureflash Photo Agency, Shutterstock
2. He Was Mr. Popularity
Later in life, James Gandolfini reflected on his Sopranos role of a lifetime: “I'm playing an Italian lunatic from New Jersey, and that’s basically what I am”. Born September 18, 1961, in Westwood, Gandolfini may have had humble beginnings, but he also had major charisma at an early age. In high school, his classmates voted him “Class Flirt” and “Best Looking”.
It wasn’t until university that his troubles started to emerge…
3. His University Days Were Wild
Most people would like their booze-fueled college antics to be left in the past—but years later, one of Gandolfini’s friends from Rutgers told all about their time together. Apparently, one night after too many drinks Gandolfini destroyed a parking gate and ended up behind bars. He was also part of a dorm fight club, which ended up earning him a nasty forehead scar.
Speaking of scars, something much worse than horseplay would inflict the 19-year-old Gandolfini with tragically deeper wounds…
Diariocritico de Venezuela, Flickr
4. He Was Mad At The World
If good actors can draw from their own pain to create complicated and authentic characters, then it is no accident that Sopranos creator David Chase called James Gandolfini a “full-fledged genius”. The fates gave Gandolfini a lot of raw material to work with when, while still a student, he suddenly lost his girlfriend of two years in a car accident.
Sadly, she wasn’t the only his only romantic partner who lost her life tragically.
Peabody Awards, CC BY 2.0, Wikimedia Commons
5. His Lady Friends Were Unlucky
Fast forward to the year 2020, which was unlucky for many, including Gandolfini’s former fiancée Lora Samoza. The pair got engaged in 2003, however, after a couple of years the relationship tanked. A crushed Samoza never really got over the heartbreak—and then, tragedy struck.
In a freak accident, she lost her life after tripping, hitting her head, and drowning in her parents’ pool. She was 51— the same age as Gandolfini when he passed on. .
6. His Side Hustle Was Shady
Like many actors, James Gandolfini had to earn a living while waiting for his big break. Unlike most actors, he worked as a bouncer at a gentleman’s club called Private Eyes. Sure it was seedy, but the on-the-job people-watching was the perfect preparation for his first major movie role as a terrifying mob enforcer in the Quentin Tarantino-penned True Romance.
For the role in the 1993 cult classic, Gandolfini even admitted that he got a lot of inspiration from a pal…who was an actual hitman.
Morgan Creek, True Romance (1993)
7. His Big Break Led To A Huge Break
As bloodthirsty as his True Romance character was, James Gandolfini grabbed headlines by bringing a disorienting likeability to the role. The Sopranos’ casting director took notice and brought Gandolfini in for an audition. Gandolfini bungled it, swore, and walked out. David Chase, the show’s creator, gave him a second and then a third chance to audition.
Little did Chase know, that Gandolfini’s touchy nature would become a frustrating theme for the show’s main star.
8. His Life Took A Head-Spinning Turn
He may not have looked like a megastar, but on January 10, 1999, the first episode of The Sopranos aired and James Gandolfini became a household name. If that wasn’t enough excitement, he married Marcy Gandolfini two months later. The following year they welcomed a son, but trouble was already brewing for the couple…
9. His Life Got Messy
The year 2002 was a disaster for Gandolfini. His marriage was over and during the bitter divorce, court documents revealed Gandolfini’s dark secrets—yes, plural—to the world. In a move that she could have swiped from The Sopranos, his disgruntled wife hired private detectives to follow Gandolfini, and let’s just say the findings were juicy.
10. He Was Out Of Control
Perhaps marrying a guy voted “Biggest Flirt” in high school was not such a good idea. During Gandolfini’s divorce, his wife made a series of shocking accusations. These included a complaint that he had several mistresses, engaged in deviant bedroom behavior, and even dated a stripper.
She also claimed that he had a penchant for illicit substances, booze, and guns. But that’s not all…
Everett Collection, Shutterstock
11. He Made Some Bad Decisions
Gandolfini’s life mirrored art when, according to court documents, his assistant found his firearm. Gandolfini confessed that he had bought the piece to use as protection when he went to Harlem in search of illicit substances. This was the last straw for Gandolfini’s wife, who cited this as the reason she was demanding sole custody of their son.
As if that wasn’t enough, the revelations just kept getting worse…
12. He Was Like Teflon
Considering all of Gandolfini’s scandals, especially so early in his career, it was a shocker that he even had one. During the divorce, his wife also accused him of being so out of control on booze and substances on the set of the 2000 Brad Pitt film The Mexican, that the entire production had to be shut down.
Interestingly, this was also the set where he met the aforementioned ill-fated fiancée Lora Samosa, whom he ended up proposing to after the divorce. Hmm.
Dreamworks, The Mexican (2001)
13. His Wife Was No Angel
Someone should have reminded Gandolfini’s wife Marcy that when you point a finger at someone, there are three pointing right back at you. Marcy Gandolfini did not escape the divorce proceedings unscathed. James blamed the breakdown of the marriage on her, claiming that she was volatile, emotionally unstable, and always threatening to end her life.
The actor’s spokesman discounted Marcy’s accusations as “the ramblings of a disgruntled ex-wife apparently looking for a payday”. Ouch.
14. He Was A Tormented Artist
During the divorce, Gandolfini’s wife also made one bizarre claim: that during their arguments, James would get so frustrated that he’d start punching himself in the face. His fellow Sopranos cast members likely found this one plausible as he sometimes made similar self-destructive gestures when he messed up on set.
Too bad his behind-the-scenes Sopranos troubles became much more serious than him hitting himself for forgetting his lines…
15. He Drew The Line
No one has described Gandolfini as a diva, but he wasn’t always eager to please on the set of The Sopranos. When he found out that one of his scenes would require his character to pleasure himself in a gas station bathroom, he threw a huge tantrum. According to the author of the HBO exposé Tinderbox, Gandolfini was prone to “fitful bouts of disruptive incredulousness”.
Speaking of disruption, that incident was nothing compared to his other on-set antics.
16. He Could Not Be Tamed
Everyone has days when they don’t want to show up at work, but if we don’t, it is not the logistical and financial nightmare that it was when James Gandolfini did it—and during his tumultuous divorce, he did it a lot. Sometimes he pretended he was sick and some days he just wouldn’t show up.
Everyone knew his irresponsible ways were the price they had to pay for his extreme talent, and to his credit, he did have some unorthodox ways of mending fences…
17. He Tried To Buy Forgiveness
Speaking of paying the price, James Gandolfini would feel such remorse for ghosting the cast and crew that the next day he would shower everyone with lavish gifts. One crew member said, “All of a sudden there’d be a sushi chef at lunch or we’d all get massages”. This behavior got to be such a pattern that when Gandolfini didn’t show up for a big expensive night shoot at the airport nobody batted an eye.
Unfortunately, the Sopranos team would soon learn that they should have been very worried.
18. He Went Over The Edge
Everyone knew Gandolfini was on the brink. He had been struggling with substances, his divorce, and carrying the weight of a megahit show, which would be a big ask for a sober, sane person. When days started passing without any word from Gandolfini, everyone started to come to the sinking realization that something was very, very wrong.
19. He Shocked His Coworkers
Something had to give. Jeff Bewkes, the CEO of HBO, later said, “We were concerned about Gandolfini staying alive”. Of course, the truth was even more of a head-scratcher. On day four of Gandolfini’s absence, a call came into The Sopranos production office. It was Gandolfini calling from a Brooklyn beauty salon and asking if someone could come pick him up.
Would his freaked-out family and coworkers forgive him for this one?
Everett Collection, Shutterstock
20. He Had Gone Too Far
Even Gandofini’s most ardent enablers and yes-men had to admit that his four-day bender pushed everyone to the brink. As much as most of the other actors loved Gandolfini, they were also getting pretty hot under the collar about having to constantly adjust their schedules to accommodate his increasingly unprofessional behavior.
The show’s team decided to put a secret plan into place…
21. He Was Caught Off Guard
Picture it: You’re a massive TV star. You’ve been invited to a casual dinner at your boss’s fancy Manhattan condo. Depending on how delusional you are, you think that you might be getting props for your show’s current success. As you walk through the door, you see about a dozen family members, HBO execs, and even The Sopranos creator huddled in a circle with concerned looks on their faces.
It was time for an intervention…and James Gandolfini was having none of it.
22. He Was Living A Nightmare
Gandolfini’s reaction to the intervention was brutal. Luckily for us, author James Andrew Miller described the intervention in all its shameful glory in Tinderbox: Gandolfini “sized up the situation in a snap, and immediately barked, ‘Oh, f--- this. F--- all of you’”. He then glared at the HBO big boss, said, “Fire me,” and stormed out.
One of Gandolfini’s sisters jumped up and chased him down the hall, but her begging fell on deaf, enraged ears.
23. His Colleagues And Fam Were Motivated
Have you ever wondered what it takes to set up an intervention for a big-time celebrity? Gandolfini’s was as logistically intense as an episode of The Sopranos. His loved ones spent two days rehearsing different scenarios and had even arranged to have a private jet on standby to whisk Gandolfini off to rehab. Too bad the whole production lasted a mere 10 seconds.
24. He Knew His Worth
Incredibly, despite the intervention fail, life on the set of The Sopranos eventually settled back down—at least for a while. Unhappy with his pay, Gandolfini’s contract negotiations almost halted the production of the show yet again. He played hardball, though, doubled his salary, and even shared his windfall by personally giving 16 of the show’s actors each a check for $33,000!
25. He Was (Kinda) Mobbed Up
James Gandolfini wasn’t a method actor—but he did go to disturbing lengths to research his role. He admitted that he got into contact with the actual Mafia to ensure that his portrayal of Tony Soprano was authentic. Apparently, when the feds were listening to a real-life wiretap, they heard one New Jersey goomba ask if The Sopranos was “supposed to be us?” Yikes.
Too bad this wasn’t the only time his quest for authenticity would put him in jeopardy…
26. He Screamed For Ice Cream
James Gandolfini was the big man on The Sopranos set—figuratively and literally. According to costar Edie Falco, the 183 cm (6’ tall), 113 kg (250 lb) actor loved to eat. For one scene, she said Gandolfini just kept refilling his ice cream bowl for each take instead of pretending to eat. “At one point I realized he’s not really listening to me—he had gone into a sugar coma!”
He was in such bad shape they had to shoot the rest of the scene another day but that wasn’t his only eating-related incident…
27. He Was In A Chilling Scene
It’s almost as if the writers for The Sopranos took some lessons in predicting the future from The Simpsons. In a chillingly prophetic intervention scene, an addicted character had some choice words for Gandolfini’s Tony: “The way you f---in’ eat, you’re gonna have a heart attack by the time you’re 50!” If they only knew then…
28. He Got A Strange Call
James Gandolfini may have played a cold-blooded character but in real life, one incident really shook him up. Late one night he got a call from an unknown number and a voice said, “Listen, you’re a great actor, we like what you’re doing, but you got to know one thing: A don never wears shorts”. In a funny twist, the show’s creator worked the line into the show.
Not all of his interactions with the public had happy endings, though…
29. A Fan Crushed Him
James Gandolfini was often described by friends and strangers as a reluctant star, but he would often go the distance for his fans. However, something unexpected happened after he autographed a fan’s bible. The fan’s mother saw the signature and spat, “No, not him. Not him”. A show executive watched him sign it as “Tony Soprano” and then quickly run from the room. She later found him “sobbing like a baby” in a pile of laundry.
The bigger the show became, the harder it was for Gandolfini to keep himself under control…
30. He Was A BYOB Pro
Heavy drinkers can be experts at hiding their bad habits—and Gandolfini was no exception. At the Golden Globes one year, HBO CEO Bewkes complained to Gandolfini about the quality of the wine they were serving. Bewkes was in for a surprise. Gandolfini then reached under the table and pulled out a bottle from the stash that he had brought to the ceremony. Bewkes said, “I drank with him thinking it would calm him down. I guess I was stupid”.
Too bad a CEO enabling his biggest star wasn’t the only Golden Globe drama...
Everett Collection, Shutterstock
31. He Did A Little Too Much Pregaming
Presenting a Golden Globe on live TV in front of an audience of millions would be pretty nerve-wracking, even for a seasoned pro like Gandolfini. Perhaps it was this pressure that caused him to act like a wild teenager during the 2005 awards ceremony. When it was nearing his time to present, tension mounted as no one was able to find him…
Featureflash Photo Agency, Shutterstock
32. He Caused A Panic (Again)
The show must go on, as they say, and at the last minute, Golden Globe execs relieved the missing Gandolfini of his presenting duties and replaced him with his Sopranos’ co-star Michael Imperioli. When Gandolfini was eventually found, he must have been a sight to behold. The incredibly inebriated actor was found doing snow angels (sans snow) on the lawn of the Beverly Hilton.
Patrick McMullan, Getty Images
33. He Had A Lot Going On
When you’re James Gandolfini in the late 2000s, there’s never a dull moment. Although one door closed when The Sopranos ended with a very, um, misunderstood finale, another opened when Gandolfini married former model Deborah Lin in a 20-minute ceremony in Honolulu. If you’re thinking that his life would finally settle down—well, not quite.
34. He Spilled The Tea
It’s always surprising when a press-shy celeb opens up publicly, and in 2012, James Gandolfini sang like a bird. Without the daily grind of The Sopranos to (kind of) keep him in check, he disclosed that although he hit rock bottom with his substance issues in 2009, he was presently “clean and sober”. This is interesting when you consider that in 2012 he only had about a year left on the planet.
That wasn’t his only shocking revelation though…
35. He Went Way Back
Again, you gotta wonder why James Gandolfini, who gave very few interviews, decided to dive deep into his past bad behavior. He even divulged that in 1997 (post-True Romance and pre-The Sopranos), the authorities caught him racing with another car and apprehended him for drinking and driving.
“Let me say it was the best French toast I ever had when they woke me up in the Beverly Hills [lockup]!” Um, if you say so? And while we’re on the topic of bizarre revelations…
36. He Wasn’t Afraid To Say No
James Gandolfini was clearly a complicated man. Case in point, his Sopranos costar Steve Schirripa gave us a peek into how Gandolfini really felt about Harvey Weinstein before the movie mogul fell from power. Gandolfini was in a 2012 film that was distributed by Weinstein’s company, and he did not like what Weinstein was asking him to do…
37. He Wouldn’t Be Pressured
Weinstein kept pressuring Gandolfini to do publicity for the movie and even got pretty nasty about it. Now if we know two things, it’s that Weinstein did not like hearing the word “no” and Gandolfini avoided the press like the plague. It was a combination that was destined for trouble. According to Schirripa, Gandolfini raged, “He f---ing calls me again, I will beat the f--- out of him!”
Gandolfini continued, “For the money he paid me, I’m not f---ing doing it! Swear to God”. Strangely enough, that’s not the only juicy revelation…
38. He Had A Housewives Connection
If you don’t think too deeply about it, you might agree that The Real Housewives of New Jersey couldn’t have existed without The Sopranos paving the way—which could have been a good thing. Nevertheless, in 2023, RHONJ friend Jennifer Fessler dropped a shocking tidbit about James Gandolfini that immediately caused the other housewives to pounce on her demanding the dirty deets—and, of course, she delivered.
39. He Wasn’t Vanilla
A Real Housewife who kisses and tells? We wouldn’t expect anything less! According to Fessler, she not only slept with a pre-fame Gandolfini but she also became “obsessed” with his animal magnetism. Fessler divulged that Gandolfini took her to an S&M bar and the pair hung out, drank (how on brand), and did the deed.
She called Gandolfini “the one who got away” and quipped, “But he absolutely was inside me that is a fact—more than once”. Stay classy, Jennifer.
40. Ladies Loved Him
Real Housewife Fessler wasn’t the only one to gush about James Gandolfini. His Sopranos costar Drea De Matteo said that she and a friend who worked on set “used to walk around and make, like, the sound of a faucet going. Meaning, like, we need a cold shower, every time we walked by Jim. Who knew that we would have crushes on this big, hulking, balding, middle-aged man?”
Unfortunately, in 2013 he would be breaking more hearts than anyone could ever imagine.
Featureflash Photo Agency, Shutterstock
41. He Took His Family On The Trip Of A Lifetime
Post-Sopranos, Gandolfini’s life was sailing along smoothly. He was busy with a variety of projects and he and Deborah Lin had a nine-month-old baby. In June 2013, when he was planning to attend a film festival in Italy, he decided to turn the trip into a family vacation to reconnect with his Italian roots. After all the upheaval in his life, wasn’t it time for a little peace?
Unfortunately, destiny had other plans...
42. He Let Loose
After a full day of sightseeing under the hot Roman sun, a jet-lagged James Gandolfini and his son decided to grab a bite in their hotel’s outdoor restaurant. The pair enjoyed a hearty meal that included fried shrimp and foie gras. Gandolfini also had a couple of pina coladas and some pints. His waiter said he “looked happy,” and a tourist even snapped a photo of him enjoying his meal without incident.
Sounds like la dolce vita, right? Wrong.
43. His Son Made A Shocking Discovery
After finishing dessert, the pair made their way back to the hotel at about 9:00 pm. At 10:00, Gandolfini’s son Michael walked into the bathroom of their suite and made a disturbing discovery. His father had collapsed on the floor. In a panic, Michael called the front desk staff and within minutes, an emergency crew arrived on the scene.
They immediately began to work on Gandolfini ,who was still alive at the time.
44. His Family Was Terrified
Within mere moments, the family’s dream vacation had turned into a complete and total nightmare. At this point, James Gandolfini was fighting for his life. First responders had wrapped a shirtless Gandolfini in a hotel blanket and were whisking him through the hotel lobby and into an ambulance. The situation wasn't looking good for the acclaimed actor.
Chairman of the Joint Chiefs of Staff, Wikimedia Commons
45. His Demons Caught Up With Him
Gandolfini arrived at the hospital at 10:40 and for 20 agonizing minutes, doctors tried to revive him to no avail. On June 19, 2013, James Gandolfini died at the age of 51. According to an autopsy, he had had a major heart attack. His spokesperson confirmed that “nothing else was found in his system”. The world was reeling from the shocking news.
46. A Paramedic Did Him Dirty
It’s not surprising to learn that on the day he perished, James Gandolfini was wearing a Rolex. What is surprising—and, frankly, disgusting—is that the paramedic who treated Gandolfini snatched it right off his fading body. To make the situation even more eerie, the paramedic had the same last name as a Sopranos character whom Tony had to off because the guy robbed his crew and even demanded a watch!
Sadly, that wasn’t the only distasteful disaster surrounding his demise.
47. His Passing Brought Out The Worst In Some People
James Gandolfini was well-loved around the world, so it makes sense that the public was fascinated with his passing. However, it is a little perplexing that a) his hotel rented out his doomed suite the very next day and b) Sandra Lee, TV personality and then-girlfriend of New York Governor Andrew Cuomo, was the one who booked it the day after Gandolfini passed.
Karma ended up catching up with Lee, though…
48. His Suite Was Doomed
To discourage ghost hunters and the morbidly curious, hotels usually take the ill-fated room out of rotation for a while, but not the hotel where James Gandolfini spent his last minutes. Sanda Lee didn’t get to spend too much time in the $671/night suite, however, as the paparazzi were constantly calling the room and even bribing hotel staff to let them take a peek.
KGGucwa, CC BY-SA 3.0,Wikimedia Commons
49. His Son Didn’t Listen
When it comes to James and his son Michael, the apple really didn’t fall far from the tree, especially when it comes to rebellious streaks. When Michael was young, James discouraged him from going into acting. He said he would prefer the boy to “be a director. They have power”. However, after losing his father, Michael decided to keep his father’s legacy alive by playing a young Tony Soprano in the 2021 film The Many Saints of Newark.
HBO, The Many Saints of Newark (2021)
50. He Didn’t Like The Ending Either
For one last time, we need to draw the connection between James Gandolfini’s art and life. In a rare interview, when he talked to Vanity Fair about the polarizing, confusing, ending of The Sopranos, he said, “What the f---? I mean, after all I went through, all this death, and then it’s over like that?” We know how you feel, James.
