The Sopranos: Tony’s Mistresses And Affairs, Ranked Worst To Best
Tony Soprano is one of the most complex characters in TV history. The womanizer had some memorable mistresses that we've now ranked.
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. He seldom cares about women for who they are. However, he ends up with some pretty amazing people – as well as some who are less impressive. With full respect to these women, these are Tony’s best mistresses and affairs, ranked.
Updated on February 4th, 2021 by Theo Kogod: It has been a long time since The Sopranos ended, but the world is still not finished with its favorite HBO mafia drama. James Gandolfini’s depiction of mob boss Tony Soprano is lauded as one of the best TV performances of all time and won him numerous awards. Now, his son Michael Gandolfini steps into the shoes of his father’s most iconic role as a younger version of Tony and, as fans look back at the show’s past, it is also worth taking a closer look at the series itself, and the many lovers of its beloved protagonist.
HONORABLE MENTION: Dr. Jennifer Melfi
The relationship between Tony Soprano and his therapist, Dr. Melfi, is one of the central narrative threads woven through the series. Tony repeatedly propositions her, offers her gifts, and flirts with her. At one point when Dr. Melfi shoots him down, 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 who 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, she 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.
Miss Reykjavik
When Tony is at a party with some of his lieutenants, several Icelandic flight attendants are brought in. 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.
While this could have easily been a one-off appearance, Tony is revealed to be sleeping with one of the women much later in the same season, implying this is a semi-regular occurrence. Identified only as Miss Reykjavik, she 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.
Annalisa Zucca
When Tony travels to Italy 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 admits he has a hard time accepting – though he has no such hesitation fantasizing about Annalisa while on the phone with Carmella.
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. Interestingly, it is this emotional and sexual chemistry that leads them to conclude a difficult business deal. While he does not technically hook up with her, the connection between them is so strong that it would be a mistake not to include Annalisa on this list.
Charmaine Bucco
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 affiliates.
However, Charmaine reveals that she and Tony had an affair years ago when Tony was dating Carmela. In a particularly spiteful moment, she tells Carmela this just to inflict pain on her longtime friend. 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.
Connie DeSapio
Connie is a receptionist who works for one of Tony’s main businesses in the waste management industry. 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 will probably not be 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.
Julianna Skiff
Julianna is a realtor who helps Tony sell a piece of property. While signing the paperwork, tension builds between them, and the moment the paperwork is finished, they begin making out, then advance to even more intense activities. However, Tony stops midway through, feeling guilty about what he is doing.
Later, Julianna attends an AA meeting for help, where she makes a connection with Tony’s cousin, Christopher Moltisanti. This proves disastrous for both of them as they enable each other to give in to their worst addictive tendencies, spiraling out of control. She later pays her respects to Chris at his funeral, where she runs into Tony.
Lorraine Calluzzo
Lorraine is a loanshark with the Lupertazzi Crime Family. When a war begins to rise over issues of succession within the Five Families, Lorraine gets caught up in it, even having Phil Leotardo threaten to kill her in a mock execution.
During the negotiations over how to handle the succession issues, Tony reveals he once slept with her. Later, she’s executed in her home. While she’s mostly forgettable, her business savvy and gutsy attitude are worth noting.
Valentina La Paz
Tony is first introduced to Valentina by Ralph Cifaretto while they are attending their horse at the stable. Valentina and Tony have a natural chemistry together and end up hooking up despite her also being involved with Ralph. Ultimately, she and Ralph split due to Ralph’s affinity for BDSM, making them incompatible.
When Tony is going through his divorce from Carmela, Valentina is Tony’s primary lover. However, after she sets herself on fire while cooking dinner, the relationship ends. At least Tony takes care of her medical bills.
Irina Peltsin
Irina is the girlfriend Tony has at the start of the show. A Russian immigrant who moved to the US, Irina has dealt with a lot, not least of all Tony’s rages and abusive tendencies. By the time she and Tony break things off, it seems he is more concerned about her in an almost paternalistic way, urging her to think about her career.
Later, Irina dates one of Tony’s associates, Ronald Zellman. Tony claims he is fine with this arrangement, then later attacks Zellman at his own home, violently assaulting the man for his relationship, which leads to Zellman breaking up with Irina.
Adriana La Cerva
Adriana and Tony never technically hook up, which is the only reason she is not higher on this list. 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 except they were interrupted – twice. Given their chemistry, it only seems fair to include her.
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. Tragically, Adriana is killed after she reveals she has been working as an informant to avoid arrest.
Gloria Trillo
Gloria is a car saleswoman who sees the same therapist as Tony, Dr. Melfi. Due to a mixup, the two meet when they are both scheduled to have appointments at the same time. The pair begin a torrid romance and Gloria falls hard for Tony. For his part, Tony is immediately influenced by her love of Zen and begins citing Eastern philosophy after their discussions.
When Gloria grows jealous of Tony’s wife and threatens him, they have a violent breakup. Tony has his henchmen threaten her life if she does not stay away. Not long after, she commits suicide.
Sonya Aragon
Sonya is one of Christopher Moltinsanti’s exes, a woman who strips to pay her way through school. After Christopher’s funeral, Tony goes out to Las Vegas where he meets Sonya. He informs her of Christopher’s passing, though omits the part about being the one to murder Christopher.
They hook up and a little while later, they do buttons of peyote together. This leads to the two wandering through a casino in an almost shamanistic experience where Tony–a button man (as the mafia call killers)–tries his luck gambling, accompanied by Sonya, who is a companion to him as he confronts the nature of fate while staring at a roulette wheel contemplating Christopher’s death. Sonya is only in one episode, but she is an unforgettable character.
Svetlana Kirilenko
Svetlana is a one-legged Russian immigrant and Irina’s first cousin. She is probably the most uncompromising stable woman Tony has ever hooked up with. Despite all she has been through, she is possessed of stoic wry confidence. When Tony comments on this, she explains that while Americans expect nothing bad to happen to them, the rest of the world expect bad things and so are never disappointed.
At one point in the series, Svetlana gets into an argument with Tony’s sister Janice, who steals Svetlana’s prosthetic leg. Rather than be daunted by someone from an organized crime family taking her legs out from under her, Svetlana just goes to the Russian Mafia for help, cool and resourceful as ever. She is pragmatic, confident, competent, and able to see the horrors of the world without being burdened by them.
