The Sopranos
The Sopranosprotagonist Tony has had a masses of extramarital affairs — and the question of which Tony Soprano kept woman / girlfriend was the best in the series is still hotly debate . More than two 10 afterThe Sopranosfirst debuted , Tony Soprano stay one of the most memorable charactersin video story . The crime syndicate boss who stomach from panic attacks was a singular character conception and made for a more nuanced mafioso than the common clichés populating crime shows at the prison term . Beyond his rage , rapacity , insecurity , and commitment to his family , Tony is also a womaniser .
Tony Soprano mistreats many of his girl throughoutThe Sopranos . However , he ends up with some pretty amazing people . Throughout six season , Tony had seven schoolmistress and several daily affairs . Each Tony Soprano mistress was different , with some assay to gain from their interactions with the don and others only out for a good time . There ’s no interrogation that the battalion of women Tony Soprano had affairs with deeply affected his marriage to Carmela , who was entirely mindful of his dalliances . disregardless , each fair sex Tony slept with had a peculiar role in the narration ofThe Sopranos .
Tony Soprano is one of the most complex and well - written fictional character in telecasting history , and The Sopranos introduced the concept of the anti - paladin .
13Dr. 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 honourable mention . The relationship between Tony and Dr. Melfi is one of the central narrative duds woven through the serial publication . Tony fosters feelings for his therapist pretty early on inThe Sopranos , and rather than respect the boundaries of a affected role - Doctor of the Church relationship , Tony makes logical grasps for more of a wild-eyed connection .
Tony repeatedly propositions her , offers her gifts , and flirts with her . At one point , Dr. Melfi shoots him down and he grows fabulously irate . subsequently , after Tony and his wife Carmela separate , he taste pursuing Melfi gravely , but ( as always ) she rebuff him . At several head , Tony haunt over this strong , intelligent womanhood to whom he feels both attracted and connected . Interestingly , at one point , Melfi confides to someone that she is attract to Tony ’s strength and confidence .
However , Dr. Melfi is a professional who would never go out a patient , and by the closing of the series , she begins to believe Tony is a psychopath , and so she distances herself from him . She ’s not one of the women Tony Soprano kip with , but the two shared a connectedness , albeit a toxic one .
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12Miss Reykjavik (Tone Christensen)
The Icelandic Flight Attendant
When Tony is at a party with some of his lieutenants inThe Sopranosseason 4 , several Icelandic escape attendants are bring in in . One of them , known as Miss Reykjavik , ends up becoming one of Tony Soprano ’s mistresses , who by and by come along in time of year 4 , installment 6 , " Everybody injure . “Tony and his men ineluctably end up kip with these fair sex , and in one of the few instance where Tony seems okay with same - sex couples , he watches two of the women make dear .
Miss Reykjavik has a genuine common sense of warmth and connection with Tony
While this could have easily been a one - off , Tony is break to be sleeping with one of the woman much later in the same season , implying this is a semi - veritable occurrence . Miss Reykjavik has a unfeigned sense of warmth and connection with Tony , express mirth 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 make brief appearances in a sum of three episode and , out of all of Tony Soprano ’s girlfriends , his kinship with the mysterious Miss Reykjavik seemed to be the most abject - key , and for once , caused very few waves in Tony ’s Clarence Day - to - day life .
11Annalisa 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 inThe Sopranosseason 2 to meet with his Neapolitan associates in the Zucca Crime Family , he learns that the genus Bos , Mauro Zucca , is serving a life condemnation . Mauro ’s wifeAnnalisa is the move boss — something Tony chauvinistically admits he has a concentrated time accepting . However , it ’s worth noting that he has no such falter fantasizing about Annalisa while on the phone with Carmela .
Despite his biases , Annalisa opens up to him , and for his part , Tony becomes potty with her . She takes him to the ancient website of Cumae , where beautiful women , do it as Sybils , once gave oracular prophecies . In the Sybils ’ cave , Annalisa propositions Tony . He confesses to feel the same way , but refuses , as she is a clientele associate degree .
Annalisa ’s plan of conquest turn out to be a no - go , and in bother , she forces Tony to lour the price of the cars . It is this worked up and sexual chemistry that go them to reason out a difficult occupation deal . While he does n’t technically hook up with her , the connection between them is very inviolable .
HBO ’s The Sopranos attain a remarkable feat with Tony . He was in the Mafia and intrust heinous crimes , yet fans empathized with him .
10Charmaine Bucco (Kathrine Narducci)
The Wife Of One Of Tony’s Oldest Friends, Artie Bucco
The melodic theme that Charmaine was ever a Tony Soprano mistress came as a cushion to audience when the verity came out inThe Sopranosseason 1 . Charmaine Bucco is the married woman of Artie Bucco , one of Tony ’s oldest friends ( and one of his only friends not ruffle up in organized crime ) . By the time the serial started , she and Artie had been together for age , and she had nothing but contempt for Tony Soprano and his business affiliate .
However , Charmaine reveals that she andTony had an affair year ago when Tony was date Carmela . While there are allusion to her and Tony ’s relationship throughoutThe Sopranos , it ’s discover the two had a past romance in time of year 1 , installment 3 , " Denial , Anger , Acceptance . " In the installment , the Buccos are rent to cater a tacit auction fundraiser at the Soprano family , and Carmela ends up treat Charmaine no better than a handmaid .
In a particularly spiteful moment , she order Carmela this just to inflict pain on her longtime friend after their friendship make a crisis point . Charmaine is not a tough person ( after all , many of the fiber on the show are murderers ) . However , her vindictive judgmental nature makes her hard to wish .
9Connie DeSapio (Jennifer Albano)
A Receptionist At One Of Tony Soprano’s Businesses
Tony Soprano is somehow able-bodied to coerce women to flex their morals , andConnie DeSapio was a pass that but should n’t have come about , as she served fiddling narrative purpose other than to demonstrate that Tony is a womaniser . Connie is a receptionist who process for one of Tony ’s main businesses in the waste product management manufacture , and her one coming into court is inThe Sopranosseason 2 , episode 11 , " House Arrest . "
When Tony ’s doctor recommend he work on stress direction techniques to cope with the strain of office work , the show immediately rationalize to Tony and Connie burn off stress together at her desk . Ultimately , Connie became just a number in the farseeing listing of women Tony Soprano had amour with .
8Julianna Skiff (Julianna Margulies)
A Realtor Who Worked With Tony Soprano
Julianna Skiff appear a handful of time inThe Sopranosseason 6 and also fosters a toxic connection with Christopher . Julianna is a realtor who help Tony sell a piece of property . He initially makes a mountain pass at her , but she declines his advance as she ’s engaged and at a good space in her lifetime . However , things between the two arrive to a head .
The moment the paperwork is finished , they commence making out , and then advance to even more acute activities
While sign the paperwork , tenseness builds between them , and the moment the paperwork is finished , they begin clear out , and then advance to even more intense activity . However , Tony stop halfway through as he feels shamefaced when he think about Carmela ’s devotion to him while taking care of him after he got shot . Later , Julianna see an AA meeting for help , where she makes a connection with Tony ’s full cousin Christopher .
This proves disastrous for both of them as they enable each other to give in to their worst addictive leaning , smoking heroin together and spiraling out of ascendency . Tony continues to act on her , but she rebuff him at every turn after his initial rejection . She later pays her respect to Chris at his funeral , where she runs into Tony and Carmela .
HBO ’s Tony Soprano is one of the greatest television characters of all time . His inescapable path from a capo to street knob led him to an unglamorous life .
7Lorraine Calluzzo (Patti D’Arbanville)
A Loan Shark With The Lupertazzi Crime Family
The Sopranosseason 5 sawanother uncommon female mafioso in Lorraine Calluzo . However , their function is n’t chronicle . Lorraine is a loanword shark with the Lupertazzi Crime Family who also had a sexual relationship with Little Carmine in the past . When a war begin to rise over issues of succession within the Five Families , Lorraine gets caught up in it . She turn away to make direct payment to Johnny Sack , despite him taking over as head of the menage after Carmine Jr. rather , she sends her payments to Carmine ’s Word , at long last result in Phil Leotardo performing a mock execution .
During the negotiations over how to handle the sequence 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 execute in her family . While she ’s mostly forgettable , her business organisation savvy and gutsy attitude are worth notice . The fact that she ’s one of the cleaning lady Tony Soprano slept with speaks to the strangely incestuous nature of the maffia thatThe Sopranospresents , as many of Tony ’s social occasion and relationships materialize within the confines of the great " family . "
6Valentina 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 date Ralph Cifaretto . Tony is first introduced to Valentina by Ralph while they are attending their Equus caballus at the stable . Valentina and Tony have a natural chemistry together and hook up despite her also being take with Ralph . in the end , she and Ralph break open due to Ralph ’s affinity for BDSM which she does not divvy up .
Things between Valentina and Tony go well for a while , but one of her simulated nails fall into his pocket and Carmela find it while she ’s doing the washing . When Tony is fit through his divorcement from Carmela , Valentina is Tony ’s primary lover . Hetries to opine Valentina as a married woman but finds it increasingly difficult as clip goes on , and he finds himself missing Carmela . One day , Valentina is cook for Tony and talking about how they should take a vacation and put her robe on fire .
After this incident , she finds herself in the infirmary with all of her haircloth burn off , and the kinship ends when Tony order he ’s going back to his wife . Valentina ’s reply was only to look at her bald-pated thoughtfulness in repulsion . At least Tony take tending of her aesculapian bills .
5Irina Peltsin (Oksana Lada)
Tony Soprano’s First Mistress On The Show
Irina is the girlfriend Tony had at the start ofThe Sopranosandremained his main goomah for the first two seasons . A Russian immigrant who move to the US , Irina has dealt with a lot , not least of all Tony ’s rages and abusive tendencies . Irina work in a section store , and the two have some wild fight during their dating arc , making audiences question if this amour is deserving it .
finally , guilty conscience worm its style into Tony ’s promontory , and he split thing off with Irina in season 2 . She became suicidal and Tony tried to get her help , but ultimately ended up have got Silvio pay her off to get out of his life-time for commodity . By the sentence she and Tony break thing off , it seems he is more concerned about her in an almost paternalistic way . by and by , Irina dates one of Tony ’s associates , Ronald Zellman .
Tony lay claim he is fine with this , then later set on Zellman at his own abode , violently assaulting the man for his relationship , which leads to Zellman get out up with Irina . In revenge , Irina causes further trouble when she outs Tony to Carmela for dating her first cousin Svetlana , who was Livia ’s caretaker .
Tony Soprano was one of television set ’s most complex case and he had the power to make buff of HBO ’s The Sopranos both love and despise him .
4Adriana La Cerva (Drea de Matteo)
Christopher’s Long-Time Girlfriend
Another Tony Soprano mistress that brings the almost incestuous nature ofThe Sopranosinto question is the assignation that never was with Adriana La Cerva . Adriana and Tony never technically hooked up . However , unlike some other women who pooh-pooh Tony ’s advances ( such as Dr. Melfi),Adriana and Tony absolutely would have become mat with one another if they had not been disturb — twice .
Tony name 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 determined women . Adriana is Christopher Moltisanti ’s fan throughout most of the serial . Due to this fact , any tryst she and Tony might have had would have necessarily caused trouble . Rumors are ablaze about a likely affair between Tony and Adriana inThe Sopranosafter the time of year 5 installing " Irregular Around The Margins . "
The episode see the two hanging out until two o’clock in the morning and taking a joyride to go take hold of cocaine that finish in a railroad car chance event . Being together at that time of night and nowhere near their respective homes pose the rumor factory churning . Tragically , Adriana is killedafter she reveals the FBI forced her to become an informant .
