The Sopranos protagonist Tony has had a multitude of extramarital affairs — and the question of which Tony Soprano mistress/girlfriend was the best in the series is still hotly debated. More than two decades after The Sopranos first debuted, Tony Soprano remains one of the most memorable characters in TV history. The mob boss who suffered from panic attacks was a unique character concept and made for a more nuanced mafioso than the usual clichés populating crime shows at the time. Beyond his rage, greed, insecurities, and commitment to his family, Tony is also a womanizer.

Tony Soprano mistreats many of his girlfriends throughout The Sopranos. However, he ends up with some pretty amazing people. Throughout six seasons, Tony had seven mistresses and several casual affairs. Each Tony Soprano mistress was different, with some seeking to gain from their interactions with the don and others simply out for a good time. There's no question that the multitude of women Tony Soprano had affairs with deeply affected his marriage to Carmela, who was wholly aware of his dalliances. Regardless, each woman Tony slept with had a special role in the narrative of The Sopranos.

13 Dr. Jennifer Melfi (Lorraine Bracco)

Tony Soprano's Personal Therapist

Though not technically a Tony Soprano mistress, Dr. Melfi's complex and charged relationship with her patient does at least deserve an honorable mention. The relationship between Tony and Dr. Melfi is one of the central narrative threads woven through the series. Tony fosters feelings for his therapist pretty early on in The Sopranos, and rather than respect the boundaries of a patient-doctor relationship, Tony makes consistent grasps for more of a romantic connection.

Tony repeatedly propositions her, offers her gifts, and flirts with her. At one point, Dr. Melfi shoots him down and he grows incredibly irate. Later, after Tony and his wife Carmela separate, he tries pursuing Melfi seriously, but (as always) she rebuffs him. At several points, Tony obsesses over this strong, intelligent woman to whom he feels both attracted and connected. Interestingly, at one point, Melfi confides to someone that she is attracted to Tony’s strength and confidence.

However, Dr. Melfi is a professional who would never date a patient, and by the end of the series, she begins to believe Tony is a sociopath, and so she distances herself from him. She's not one of the women Tony Soprano slept with, but the two shared a connection, albeit a toxic one.

12 Miss Reykjavik (Tone Christensen)

The Icelandic Flight Attendant

When Tony is at a party with some of his lieutenants in The Sopranos season 4, several Icelandic flight attendants are brought in. One of them, known as Miss Reykjavik, ends up becoming one of Tony Soprano's mistresses, who later appears in season 4, episode 6, "Everybody Hurts." Tony and his men inevitably end up sleeping with these women, and in one of the few instances where Tony seems okay with same-sex couples, he watches two of the women make love.

Miss Reykjavik has a genuine sense of warmth and connection with Tony

While this could have easily been a one-off, Tony is revealed to be sleeping with one of the women much later in the same season, implying this is a semi-regular occurrence. Miss Reykjavik has a genuine sense of warmth and connection with Tony, laughing playfully with him as they lie together in bed. Unfortunately, they are interrupted when Tony’s friend Artie calls, crying after having just attempted suicide.

A short while later, Tony begins a relationship with Valentina La Paz. She makes brief appearances in a total of three episodes and, out of all of Tony Soprano's girlfriends, his relationship with the mysterious Miss Reykjavik seemed to be the most low-key, and for once, caused very few waves in Tony's day-to-day life.

11 Annalisa Zucca (Sofia Milos)

The Boss Of The Zucca Crime Family

This mistress could've spelled real trouble for the mafioso had he gone through with the full deed. When Tony travels to Italy in The Sopranos season 2 to meet with his Neapolitan associates in the Zucca Crime Family, he learns that the boss, Mauro Zucca, is serving a life sentence. Mauro’s wife Annalisa is the acting boss — something Tony chauvinistically its he has a hard time accepting. However, it's worth noting that he has no such hesitation fantasizing about Annalisa while on the phone with Carmela.

Despite his biases, Annalisa opens up to him, and for his part, Tony becomes smitten with her. She takes him to the ancient site of Cumae, where beautiful women, known as Sybils, once gave oracular prophecies. In the Sybils’ cave, Annalisa propositions Tony. He confesses to feeling the same way, but refuses, as she is a business associate.

Annalisa's plan of seduction turns out to be a no-go, and in annoyance, she forces Tony to lower the price of the cars. It is this emotional and sexual chemistry that leads them to conclude a difficult business deal. While he doesn't technically hook up with her, the connection between them is very strong.

10 Charmaine Bucco (Kathrine Narducci)

The Wife Of One Of Tony's Oldest Friends, Artie Bucco

The idea that Charmaine was ever a Tony Soprano mistress came as a shock to audiences when the truth came out in The Sopranos season 1. Charmaine Bucco is the wife of Artie Bucco, one of Tony's oldest friends (and one of his only friends not mixed up in organized crime). By the time the series started, she and Artie had been together for years, and she had nothing but contempt for Tony Soprano and his business s.

However, Charmaine reveals that she and Tony had an affair years ago when Tony was dating Carmela. While there are allusions to her and Tony's relationship throughout The Sopranos, it's revealed the two had a past romance in season 1, episode 3, "Denial, Anger, Acceptance." In the episode, the Buccos are hired to cater a silent auction fundraiser at the Soprano home, and Carmela ends up treating Charmaine no better than a servant.

In a particularly spiteful moment, she tells Carmela this just to inflict pain on her longtime friend after their friendship reaches a crisis point. Charmaine is not a bad person (after all, many of the characters on the show are murderers). However, her vindictive judgmental nature makes her hard to like.

9 Connie DeSapio (Jennifer Albano)

A Receptionist At One Of Tony Soprano's Businesses

Tony Soprano is somehow able to coerce women to bend their morals, and Connie DeSapio was a fling that simply shouldn't have happened, as she served little narrative purpose other than to prove that Tony is a womanizer. Connie is a receptionist who works for one of Tony's main businesses in the waste management industry, and her one appearance is in The Sopranos season 2, episode 11, "House Arrest."

She demonstrates thoughtfulness at her job, something her predecessor lacked. When Tony comments on her body, he is told she is a born-again Christian who's not interested in him. Despite this, he later manages to hook up with her, as he has nothing else to do while spending time at a legitimate business.

When Tony's doctor recommends he work on stress management techniques to cope with the strain of office work, the show immediately cuts to Tony and Connie burning off stress together at her desk. Ultimately, Connie became just a number in the long list of women Tony Soprano had affairs with.

8 Julianna Skiff (Julianna Margulies)

A Realtor Who Worked With Tony Soprano

Julianna Skiff appears a handful of times in The Sopranos season 6 and also fosters a toxic connection with Christopher. Julianna is a realtor who helps Tony sell a piece of property. He initially makes a at her, but she declines his advances as she's engaged and at a good place in her life. However, things between the two come to a head.

The moment the paperwork is finished, they begin making out, and then advance to even more intense activities

While g the paperwork, tension builds between them, and the moment the paperwork is finished, they begin making out, and then advance to even more intense activities. However, Tony stops midway through as he feels guilty when he thinks about Carmela's devotion to him while taking care of him after he got shot. Later, Julianna attends an AA meeting for help, where she makes a connection with Tony's cousin Christopher.

This proves disastrous for both of them as they enable each other to give in to their worst addictive tendencies, smoking heroin together and spiraling out of control. Tony continues to pursue her, but she rebuffs him at every turn after his initial rejection. She later pays her respects to Chris at his funeral, where she runs into Tony and Carmela.

7 Lorraine Calluzzo (Patti D'Arbanville)

A Loan Shark With The Lupertazzi Crime Family

The Sopranos season 5 saw another rare female mafioso in Lorraine Calluzo. However, their affair isn't chronicled. Lorraine is a loan shark with the Lupertazzi Crime Family who also had a sexual relationship with Little Carmine in the past. When a war begins to rise over issues of succession within the Five Families, Lorraine gets caught up in it. She refuses to make direct payments to Johnny Sack, despite him taking over as head of the family after Carmine Jr. Instead, she sends her payments to Carmine's son, ultimately resulting in Phil Leotardo performing a mock execution.

During the negotiations over how to handle the succession issues, Tony reveals he once slept with her. After the mock execution fails to intimidate Calluzo into paying Johnny directly, he sends Joey Peep and Billy after her. Later, she's executed in her home. While she's mostly forgettable, her business savvy and gutsy attitude are worth noting. The fact that she's one of the women Tony Soprano slept with speaks to the oddly incestuous nature of the mafia that The Sopranos presents, as many of Tony's affairs and relationships happen within the confines of the greater "family."

6 Valentina La Paz (Leslie Bega)

Tony's Main Mistress While Broken Up From Carmela

The Tony Soprano mistress for seasons 4 and 5 was Valentina La Paz, a Cuban-Italian who is also dating Ralph Cifaretto. Tony is first introduced to Valentina by Ralph while they are attending their horse at the stable. Valentina and Tony have a natural chemistry together and hook up despite her also being involved with Ralph. Ultimately, she and Ralph split due to Ralph's affinity for BDSM which she does not share.

Things between Valentina and Tony go well for a while, but one of her fake nails falls into his pocket and Carmela finds it while she's doing the laundry. When Tony is going through his divorce from Carmela, Valentina is Tony's primary lover. He tries to imagine Valentina as a wife but finds it increasingly difficult as time goes on, and he finds himself missing Carmela. One day, Valentina is cooking for Tony and talking about how they should take a vacation and sets her robe on fire.

After this incident, she finds herself in the hospital with all of her hair burned off, and the relationship ends when Tony says he's going back to his wife. Valentina's response was simply to look at her bald reflection in horror. At least Tony takes care of her medical bills.

5 Irina Peltsin (Oksana Lada)

Tony Soprano's First Mistress On The Show

Irina is the girlfriend Tony had at the start of The Sopranos and remained his main goomah for the first two seasons. A Russian immigrant who moved to the US, Irina has dealt with a lot, not least of all Tony's rages and abusive tendencies. Irina works in a department store, and the two have some wild fights during their dating arc, making audiences question if this affair is worth it.

Eventually, guilt worms its way into Tony's head, and he breaks things off with Irina in season 2. She became suicidal and Tony tried to get her help, but ultimately ended up having Silvio pay her off to get out of his life for good. By the time she and Tony break things off, it seems he is more concerned about her in an almost paternalistic way. Later, Irina dates one of Tony's associates, Ronald Zellman.

Tony claims he is fine with this, then later attacks Zellman at his own home, violently assaulting the man for his relationship, which leads to Zellman breaking up with Irina. In retaliation, Irina causes further trouble when she outs Tony to Carmela for dating her cousin Svetlana, who was Livia's caretaker.

4 Adriana La Cerva (Drea de Matteo)

Christopher's Long-Time Girlfriend

Another Tony Soprano mistress that brings the almost incestuous nature of The Sopranos into question is the tryst that never was with Adriana La Cerva. Adriana and Tony never technically hooked up. However, unlike some other women who reject Tony's advances (such as Dr. Melfi), Adriana and Tony absolutely would have become entangled with one another if they had not been interrupted — twice.

Tony mentions to Dr. Melfi that he's attracted to Adriana, and despite his misogyny, this is one more shred of proof of his attraction toward intelligent and driven women. Adriana is Christopher Moltisanti's lover throughout most of the series. Due to this fact, any tryst she and Tony might have had would have inevitably caused trouble. Rumors are ablaze about a potential affair between Tony and Adriana in The Sopranos after the season 5 installment "Irregular Around The Margins."

The episode saw the two hanging out until two o'clock in the morning and taking a joyride to go grab cocaine that ended in a car accident. Being together at that time of night and nowhere near their respective homes got the rumor mill churning. Tragically, Adriana is killed after she reveals the FBI forced her to become an informant.