All 16 of Tony’s Mistresses on The Sopranos, in Order

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As a devoted fan of “The Sopranos,” I can’t help but marvel at Tony Soprano’s intricate character development and the profound impact he has had on popular culture. His life is a fascinating study of power, loyalty, and the dark underbelly of American society.

Mobsters are no saints, and as one of the most influential Cosa Nostra members in New Jersey, Tony Soprano was a man of many sins. Among the things The Sopranos‘ central character enjoyed the most was breaking the sixth and seventh biblical commandments. Whenever he wasn’t killing someone, he was bedding a random woman or a long-term mistress. While all this was happening, Carmela was sitting at home, enjoying the splendor that came with being a mob wife.

The series repeatedly underscored that keeping a mistress is prevalent in the mob lifestyle. Despite Carmela being aware of it, she was still wounded by this behavior. However, in an attempt to retaliate, she engaged in emotional infidelity by kissing Vic Musto, flirting with Tony’s right-hand man, Furio, and sleeping with A.J.’s counselor, Robert Wegler. Yet, she found it impossible to outmaneuver Tony in this game of betrayal.

Concerning his romantic encounters, Tony was quite active, even making the legendary basketball player Wilt Chamberlain envious. Given that he had wealth, power, and a charisma reminiscent of a ladies’ man, it’s no surprise. So, let’s take a look at Tony’s infidelity record, if I may, listed here in order, as much as we can confirm.

16 Charmaine Bucco

Pre-series

In the beginning of The Sopranos, it’s disclosed that Charmaine had been married to Tony’s longtime friend Artie for quite some time. As the series progresses, viewers discover that there is a past connection between her and Tony. Growing weary of being treated as domestic help by Carmela, Charmaine seeks revenge by exposing that she had a romantic encounter with Tony during their high school years. This incident allegedly took place when Carmela was away on a trip with her parents.

Tony Started Young

Charmaine’s revelation makes it clear that Tony’s unfaithfulness is nothing new. His tendency to stray didn’t start with his rise in power and wealth; it was a trait he had all along. He’s always been on the lookout for a fresh companion. Throughout the series, it seems as though Tony has never truly moved on from Charmaine. He phones her while at the Plaza Hotel and still dreams about her. Interestingly, Charmaine wouldn’t have mentioned this if she wasn’t a bit envious of Carmela, but their relationship never strays into inappropriate territory as adults.

15 Lorraine “Lady Shylock” Calluzo

Pre-series

In the fifth season’s episode titled “Rat Pack,” it is disclosed that Tony had a past relationship with Lorraine Calluzo, also known as Lady Shylock, before the series began. She is a loan shark and an associate of the Lupertazzi crime family who is notorious for her debt collection tactics. Her trouble starts when she refuses to increase her payments to Johnny Sack. As a result, Phil Leotardo orders hitmen to eliminate her.

Breaking Protocol?

For quite some time, it appears that Tony doesn’t show interest in women who share his criminal background like Annalisa Zucca from the Camorra. In Season 2, when she tries to pursue him, he turns down the mob boss, citing business reasons. However, this isn’t the case with Lorraine, as we see a different response from Tony when they reconnect. Interestingly, it seems that Tony didn’t have any lingering feelings for Lorraine, suggesting their relationship was brief and casual.

14 Irina Petsin

“Pilot” (Season 1, Episode 1)

Over the course of four seasons, the tale of Tony and Irina unravels gradually under the watchful gaze of spectators. They take turns being a captivating duo and exhibiting harmful behavior. For a significant period, Irina’s obsession with the mobster becomes evident as she seeks purpose, meaning, and self-discovery. Eventually, Tony grows weary of her, and when she discovers he has been having an affair with his cousin, she confides this in Carmela.

Tony’s Most Impactful Mistress

1. Irina occasionally appears on the program, but manages to stay longer than any other mistress. Tony continues to keep her close because he not only has feelings for her, but also recognizes her worth. Irina’s relationship with Assemblyman Zellman demonstrates that she deserved a better situation all along. He invests in her education and assists her in adapting to American culture more comfortably. Unfortunately, Tony prevents the two from dating peacefully. He humiliates Zellman by assaulting him with a belt. Predictably, their relationship comes to an end as a result.

13 Connie DeSapio

“House Arrest” (Season 2, Episode 11)

As a film critic, I found myself immersed in a gritty tale unfolding at Barone Sanitation, a seemingly ordinary garbage company that masked a web of illicit activities orchestrated by Tony’s crew. Upon his visit, Tony was introduced to Connie, the office assistant, whose charm immediately caught his eye. The narrative took an unexpected turn when the doctor advised Tony to manage his stress, and the scene transitioned to a clandestine rendezvous between Tony and Connie, unfolding their secret affair right in the heart of the office.

No Seduction Hurdle Is Too Big for Tony

Connie, who’s known as an unattainable target, has an unexpected twist. When Tony comments on her seemingly ideal physique, he’s told she’s a born-again woman, making it unlikely for a mobster like him to get close. It turns out that she’s not just born again, but also has a past in the adult entertainment industry, which isn’t surprising given her ties to a criminal organization. Sadly, she doesn’t contribute much to the story other than demonstrating Tony’s seductive skills.

12 Mandee

“University” (Season 3, Episode 6)

In one of the show’s more brutal episodes, much of the mayhem can be attributed to Ralph. He ends up killing his girlfriend, Tracee, after she challenges his masculinity, and nearly blinds Georgie during a botched attempt to recreate a scene from Gladiator. Interestingly, Tony could have prevented the latter incident, but he was otherwise occupied – engaged in an intimate moment with Mandee in the VIP room at that time.

Not One of Tony’s Proudest Moments

1. Tony’s latest silent companion remains expressionless, making it challenging to discern her sentiments or purpose. It’s crucial for Tony to exercise greater caution when managing workers linked with any ventures under the DiMeo crime family. Previously, Georgie disclosed a distasteful fact, informing a novice dancer that to work in the VIP area, they must pay him $50 initially and perform an additional service later on.

11 Gloria Trillo

“He Is Risen” (Season 3, Episode 8)

It’s possible that David Chase doesn’t explicitly say this, but one could speculate that Gloria Trillo might have been modeled after Miss Forrest from Fatal Attraction. Tony initially encounters the lovelorn car saleswoman in Dr. Melfi’s waiting room, and he takes the opportunity to pursue her. However, their relationship turns sour as Gloria proves to be a troubled woman, a nightmare for any unfaithful man. The situation escalates dramatically when Gloria becomes overly clingy, causing Tony to take extreme measures to push her away.

The One Tony Regrets the Most

The entire Gloria Trillo plot is a scathing satire on infidelity and greed. The character herself is a perfect reminder that love can mollify only when it is radiated by both parties. The Trillo affair also symbolizes a trap for Carmela and a comeuppance for Tony. Just an episode earlier, Carmela had been advised by Dr. Krakower to leave him. Now there is another mistress.

For Tony, Trillo’s funny behaviors are somewhat a subtle revenge for his past infidelities. However, this sensation doesn’t last long since soon after the ‘Trillo incident’, Tony resumes his pattern of pursuing multiple women.

10 Miss Reykjavik

“Everybody Hurt” (Season 4, Episode 6)

During Season 4, some New Jersey mobsters are caught attending an extravagant party reminiscent of Caligula, alongside a few Icelandic flight attendants. One of them, Miss Reykjavik, becomes Tony’s short-term girlfriend. When Artie suffers a beating while trying to collect a debt from Jean-Philippe, he contacts Tony. Upon answering the call, it is evident that Tony and Miss Reykjavik are in a smooth-sailing relationship, as she is visible next to him on the phone.

Vanished Too Soon

1. Character Miss Reykjavik was lively and full of the ‘live in the moment’ spirit, it’s unfortunate she didn’t stay longer. Unfortunately, Artie disrupted the touching scene between a woman who navigates through the skies and a man who works on land. It’s intriguing to note that Miss Reykjavik makes her entrance just after Hugh shares his tale about contracting diverticulitis during his time in Iceland. This merely underscores the greatness of The Sopranos.

9 Valentina La Paz

“Mergers and Acquisitions” (Season 4, Episode 8)

Although Tony may not have shown the potential to be a varsity athlete, he had all the signs of being a charmer who could easily win over women. Valentina is presented as Capo Ralph Cifaretto’s girlfriend, and when Tony encounters her at the stables, he makes up his mind to pursue her romantically. However, this choice ultimately leads to regret on Tony’s part. At one instance, Valentina’s nail accidentally slips into Tony’s pocket, and Carmela discovers it. Enraged, she goes to a secret spot where Tony keeps his money and takes some cash for herself. Later, she initiates the process of filing for divorce.

Could Have Evolved Into Something Bigger

Valentina seems more emotionally grounded than most of Tony’s past lovers, opening up the possibility for her to become his wife. After Carmela departs from Tony, he continues seeing Valentina and it appears she genuinely cares for him. She even proposes a trip to Antigua for a romantic getaway, indicating her vision of a future together. However, Tony remains uncertain. Unfortunately, when her hair is singed in a fire accident, the head of the DiMeo crime family uses this incident as an excuse to end things permanently with her.

8 Svetlana Kirilenko

(Season 4, Episode 10)

In the show, Svetlana, who is a relative of Tony’s former girlfriend, begins working as both Livia’s live-in nurse and later, Junior’s caregiver. As a child, she suffered from osteosarcoma and had to undergo leg amputation. It isn’t until Season 2 that Tony starts a relationship with her, but it takes him some time. This affair is what eventually infuriates Irina, causing her to confide in Carmela about Tony’s extensive romantic history.

Arguably the Toughest of Tony’s Mistresses

It’s impossible not to like Svetlana. She loves her vodka, works hard, and never lets anyone take her for granted. When Tony’s sister, Janice, takes her prosthetic leg during her feud, she sends the Russian mob after her. On top of that, Svetlana has a realistic outlook on sex and love. She is quick to nip the affair in the bud instead of letting Tony use her for long and calls him out on several issues.

“What sets you apart from many others is your tendency to anticipate only good outcomes, while many others around the globe are more accustomed to bracing themselves for adversity—and they rarely find themselves disappointed.”

Instead of the typical dynamics found with most lovers, Tony and she have deep intellectual conversations covering various subjects, and she usually prevails in these discussions.

7 A Weightlifter and a Preschool Assistant

“Whitecaps” (Season 4, Episode 13)

The turbulent relationship between Carmela and Tony was solidified as one of television’s most challenging pairings by their Whitecaps-defined dynamic. Earlier on, Tony had shown Carmela a seaside home and pledged to purchase it for her; they shared a kiss and looked back at memories they’d made.

“During our financially struggling times, this was the grandest dream for caviar that we could conceive. It seems somewhat reminiscent of the Kennedy estate, doesn’t it?”

Afterward, I, as a cinephile, found myself in a tumultuous situation when Irina, Tony’s mistress, dialed our home phone. She confessed her indiscretions to Carmela, sending shockwaves through our household. In the heat of the moment, she mentioned two other women whom Tony had been seeing – a weightlifter and a preschool assistant.

The Straw that Broke Carmela’s Back

Tony finds a preschool assistant particularly appealing among his list of favorite companions. While it may seem unusual for a bodybuilder, given the context, it’s not hard to understand why. After all, there’s a picture of boxing legend Rocky Marciano hanging on his wall at some point.

Reflecting on Carmela’s character in this movie, it’s evident that she embodies the typical Cosa Nostra wife persona. Although she has grown accustomed to her husband’s infidelities, the sudden influx of incriminating information is a burden she wasn’t prepared for. She’s always kept their family separate from his outside activities, but this time, it’s become unavoidable. It’s no wonder she’s overwhelmed with anger and confusion.

6 Unnamed Dermatologist

“Cold Cuts” (Season 5, Episode 10)

In the fifth season’s episode titled “Irregular Around the Margins,” the dermatologist makes her debut. She matches Tony’s pattern of romantic interests, and while he’s receiving treatment, he attempts to flirt with her. However, surprisingly, she rejects his advances. Jump ahead to the episode “Cold Cuts,” and there she is, descending his stairs. In a surprising turn of events, the dermatologist appears to be embarrassed when Paulie visits Tony at Livia’s house, giving an impression of a ‘walk of shame.’

The Don Knows How to Turn Things Around

At first, it seemed like Tony’s attempt at picking someone up had reached a dead end, but it would have been interesting to see how he managed to turn things around in his favor. However, as Lefty from ‘Donnie Brasco’ might put it, there’s not much more to add here. If you’re curious about the specifics of the seduction process, I’m afraid I can’t help you with that. The Don always gets what he wants. Just understand that when the Don makes his move, he rarely misses.

5 Unnamed Escort at the Plaza Hotel

“The Test Dream” (Season 5, Episode 11)

In a plush room at The Plaza Hotel, Tony attempts to reach Charmaine Bucco on the phone, but she rebuffs him instead. Later, he’s drawn into purchasing services from an escort agency named Ladies of Jade, stirred by a TV advertisement. Upon her arrival, they engage in intimacy. However, his moment of relaxation following their encounter is short-lived as news about Tony Blundetto’s mistakes surfaces promptly afterward.

A Quick Tryst Born Out of Boredom and Frustration

“One of the most outstanding episodes from ‘The Sopranos’ series is titled ‘The Test Dream.’ This episode provides a deep exploration into Tony’s psychological makeup. Not only does it include some peculiar dreams, but it also portrays Tony as a fading conqueror. Since he has always been successful in acquiring what he desires, his frustration arises when Charmaine denies him her time. Even upon checking into the hotel, he encounters Dr. Melfi, another individual who turned him down. Sleeping with an escort serves more as a comfort during this time of rejection.”

4 Julianna Skiff

“Johnny Cakes” (Season 6, Episode 8)

As a movie enthusiast, I was initially reluctant when realtor Julianna Skiff approached me with an offer to buy the building where Caputo’s Live Poultry resides. I felt that small, family-owned businesses contribute significantly to a neighborhood’s unique character. However, her tempting proposal made it hard to resist. Things took an intriguing turn when she hinted at possibly sweetening the deal with a personal touch. Later, we sealed the deal at her residence and before long, our conversation shifted into something more intimate, leading us to share a passionate kiss.

A Rare Moment of Regret

On this occasion, Tony shows an unusual level of self-control. Following the kiss, Julianna starts to undo Tony’s shirt, but the gangster reconsiders and departs instead. This decision is prompted by Carmela’s recent actions. He not only recalls her kindness in nursing him after he was wounded, but also the way she buttoned his shirt.

However, it seems Tony had deceived someone. Weeks afterward, he attempted to retract his supposed remorseful actions by pursuing Julianna once more. This time, she turned him down. To add insult to injury, she chose Christopher instead.

3 Unnamed Bada Bing Dancer

“Cold Stones” (Season 6, Episode 11)

While Carmela is off enjoying herself in Paris, it’s revealed that Tony has been spending his time with a dancer from the Bada Bing club. A scene of her admiring Duccio di Buoninsegna’s famous painting, Madonna and Child, is followed by one of Tony receiving oral sex from the same dancer while he’s driving. However, it’s important to note that Tony has never needed Carmela’s absence to cheat in the past.

Disproportionate Love

In “Remember When,” much like the anonymous dancer from Bada Bing, her role serves primarily to underscore Tony’s shortcomings. Prior to departing for Paris, Carmella reminded him of her love, and she inquired if he recalled her expressing those sentiments during his hospital stay. His response was dismissive: “No!” Despite the evident emotional disparity between them, this tension is a significant part of what makes their relationship intriguing.

2 Unnamed Escort

“Remember When” (Season 6, Episode 15)

In this tense episode, Tony and Paulie find themselves in Miami as they try to avoid scrutiny after the FBI recovers the body of Willie Overall, a man Tony owes his criminal career to, following Larry Boy Barese’s decision to cooperate with authorities. Meanwhile, Tony ponders the possibility of eliminating Paulie on a boat due to his betrayal in sharing Ralph’s insensitive joke about Ginny Sack with Johnny Sack.

The best moment comes when Tony and Paulie are having dinner. They are both shown to have acquired fresh dates and when Paulie begins reminiscing, Tony shuts him down with the iconic quote,

“Remember when’ is the lowest form of conversation.”

Fun Is a Priority for Tony

This unidentified companion doesn’t significantly influence the storyline. Instead, her role primarily underscores Tony’s status as an unrestrained hedonist. Despite potentially grim circumstances for him, he still prioritizes satisfying his sensual needs. Furthermore, the presence of this companion underscores a crucial aspect of “this thing of ours,” highlighting its significance in the story.

It’s inappropriate for gang members like Tony to discuss their activities openly, particularly in the presence of those who aren’t part of the gang. So, it’s no surprise that Tony gets irritated when Paulie shares stories from the past with their dates instead of keeping quiet about it.

1 Sonya Aragon

“Kennedy and Heidi” (Season 6, Episode, 18)

It’s quite surprising that Tony chose to console the former lover of the mobster he assassinated, Sonya, who was once linked with Christopher. Just after killing Christopher (leaving out the detail about manipulating Christopher’s death by pinching his nose following a car accident), Tony travels to Las Vegas and sympathizes with her loss, neglecting to mention his role in it.

Sonya Represents Tony’s Lack of Remorse and Loyalty

Christopher, one of Tony’s most valued lieutenants, was once viewed by Tony as the likely successor to lead the family. However, personal issues related to drugs hindered Christopher from realizing his full potential. Despite seeing Christopher as something akin to a father figure, Tony didn’t express any remorse. To him, Chris was no more, and life had to continue. In the show, he encounters Sonya, spends the night with her, and openly displays their relationship while gambling in Las Vegas casinos without showing any regret.

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2024-08-31 05:33