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15 Of The Hottest Gangster Mistresses To Grace Our TVs

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15 Of The Hottest Gangster Mistresses To Grace Our TVs

via Hollynolly / picsofcelebrities

The world has been fascinated with organized crime long before Charles “Lucky” Luciano first cultivated the Five Families, which controlled New York City in the 20th century. Even when Bonnie and Clyde were robbing banks, stores, and gas stations during the “Public Enemy” era in the 30s, the public was obsessed with newspaper clippings that revealed all the juicy details of their crime sprees and ultimate death. The fascination grew exponentially once Hollywood began depicting all of the glamorous aspects of the mobster lifestyle with hit films like Goodfellas and Casino. From flashy suits to bundles of cash, film was able to capture the heyday of the mob in a way that made this lifestyle truly appealing.

Besides the constant violence, incarceration and ultimate death, there were other negative aspects to the mobster lifestyle that have also been seen on the big screen and TV. While there always seems to be an emphasis on family and most of the mobsters seen onscreen have a wife and children, that doesn’t mean that they are known for upholding the sanctity of marriage. In fact, mobsters are known for their philandering ways and it is practically accepted as part of that lifestyle. In Goodfellas, the main character stated “Saturday night was for wives, but Friday night at the Copa was always for the girlfriends.” In the HBO series The Sopranos, the characters referred to the mistresses as “goomahs” or “goomars.” Although it didn’t usually end well for anyone involved, some of these mobster mistresses added some much-needed sex appeal onscreen. Check out our list of the 15 hottest mistresses from onscreen mobsters and see the women that were too good to pass up.

15. Alicia Witt

via Pinterest / HBO

Alicia Witt was introduced to the HBO series during episode 7 of Season 2 when Christopher Moltisanti went to meet his cousin and his fiancée, Amy Safir. Witt’s character was an associate of Jon Favreau and begins having a more intimate relationship with Moltisanti after asking him to visit the set. Christopher and Amy end up having sex in her hotel room and it’s clear that he isn’t just drawn to her because of her help in his career in the film industry. However, a drugged out interaction between Moltisanti and Favreau causes them to have a twist in their dynamic and it becomes obvious that Amy no longer cares to continue their relationship. While she didn’t last long as a “goomar” on the side while he was cheating on Adriana La Cerva, the scene involving her disrobing in the hotel room was worth the price of admission for Witt’s performance in The Sopranos.

14. Annabella Sciorra

via HBO

When Tony Soprano met Gloria Trillo in the office of Dr. Melfi’s office during Season 3 of The Sopranos, audiences knew that this wouldn’t be a relationship made in heaven. It definitely isn’t a good sign when meeting someone in the office of a psychiatrist, even if it means that she is at least seeking out treatment to better her mental health. The relationship ultimately ended but not before fans got to see a variety of super sexy ensembles worn by the actress Annabella Sciorra. From the sophisticated ensembles she wore at Dr. Melfi’s office and at Globe Motors to the various lingerie shots when she was intimate with Tony, Sciorra gave an expert performance as the mentally unstable (but super hot) mistress of Tony Soprano. Sciorra was able to make a few appearances on the series even after Tony ended his relationship with her character and even after her suicide. It seems like even Tony missed seeing her beautiful face and physique but it also could have been out of guilt since things didn’t exactly end on good terms between the two of them.

13. Julianna Margulies

via HBO

Julianna Margulies was first introduced as a realtor during Season 6 of The Sopranos and Tony Soprano became interested in her romantically. While she was definitely willing after inviting him to her place and popping open some alcohol, it was actually Tony that decided not to go through with it. He ultimately had a change of heart and tried to win her back but she had already moved on and eventually fell into the arms of Christopher Moltisanti. After connecting through mutual addiction issues, the pair ultimately began an affair. Moltisanti was married to Kelli already and she was pregnant with their first child. In fact, there was a time when she called him with a pregnancy craving and he was out on a date with Margulies’ character, Julianna Skiff. Most of her time on the series was filled with some pretty unattractive moments of her being strung out on drugs but there were definitely some highlight moments where she looked all put together and exuded major sex appeal.

12. Kelly Macdonald

via HBO / screenertv

When Nucky Thompson first met Margaret Shroeder in Boardwalk Empire, she was asking that Nucky might give a job to her husband. Instead, this little visit set into motion a series of events that eventually led to the death of Shroeder’s husband and a subsequent affair between Nucky and Margaret. Played by Kelly Macdonald, this character was completely different than his current girlfriend, Lucy Danziger. For a time, Macdonald’s character was the girlfriend he was cheating on his full-time girlfriend with and she didn’t seem the least bit ashamed at their situation. Lucy tried desperately to hold onto Nucky but all of her little tricks didn’t work in the end. Macdonald’s character wound up marrying Nucky but he didn’t end up staying faithful to her either. Turn around must be fair play since she wound up having an affair with Nucky’s underling, Owen Slater, before his untimely death as well.

11. Oksana Lada

via The Sopranos Wiki / NASIOC.com

Oksana Lada is the actress that portrayed Irina Peltsin, who was the first real girlfriend of Tony Soprano that audiences got to know in the hit HBO series The Sopranos. When she was first introduced in Season 1 of the series, she seemed like the typical “other woman” due to the fact that she rarely wore actual clothes and she seemed to relish in the gifts Tony showered her with. When the series began divulging a little more information on Irina’s background and her fragile state of mind, people (include Tony) began feeling sorry for this “goomar.” Tony eventually broke off their relationship but that wasn’t the end of Irina until Season 4 of the series. In fact, she was the reason why Carmela wound up kicking Tony out of the house because Irina called and confronted Carmela on the phone. While she turned out to be a huge headache in Tony’s life, audiences sure got to see some great shots of her in lingerie and various states of undress whenever she appeared onscreen.

10. Gina Mastrogiacomo

via Goodfellas ECigarettes

In the 1990 film Goodfellas, Henry Hill began a love affair with Karen that appeared to result in a somewhat happy marriage for all accounts. Yet, that didn’t stop him from having a girlfriend on the side, by the name of Janice Rossi. The same fiery passion he once had for Karen was shown for his girlfriend and he even roughed up her boss so that she could do whatever she wanted. He basically made a second life for himself with Janice, even setting her up in a lavishly decorated apartment. Because the film was made to appear in a particular era, Janice didn’t exactly have the most fetching hairstyle. However, the actress playing her, Gina Mastrogiacomo, was much prettier than her character would allow. It was obvious that she had a beautiful figure in the film and as long as viewers could get passed her puffed out bangs and overly teased hair, Mastrogiacomo was some great eye candy for those rooting Hill on for having his “goomar” on the side.

9. Alla Kliouka Schaffer

via HBO

When Tony was in need of a nurse for his mother, he wound up hiring Irina’s cousin, Svetlana Kirilenko, in the TV series The Sopranos. Although his relationship with Irina didn’t work out, Svetlana more than earned her keep since she was the only nurse that could handle Livia without being driven away. After Livia’s death, Svetlana and Tony seemed to have a camaraderie from their past experiences with Livia. When Tony’s Uncle Junior was in need of a nurse, it was Svetlana that helped set up his new caregiver. It was during a visit to Uncle Junior’s house that Tony and Svetlana began taking their relationship to the next level. While she didn’t become Tony’s next full-on girlfriend, she was definitely a woman on the side that he wanted to keep having relations with. As long as you can get over the puffy bangs and one-leg feature (which Tony seemed to do with ease), Schaffer is actually a beautiful woman with some soft and feminine features. She also had a can-do attitude that made her even more appealing.

8. Debi Mazar

via NewYorkFreestyle.com

While most people remember Debi Mazar for the publicist character she portrayed in HBO’s Entourage series, she actually played a mistress character on the big screen long before she was helping Vincent Chase with his career. In the 1990 film Goodfellas, Debi Mazar’s character was actually friends with Henry Hill’s mistress, Janice Rossi. Yet, their relationship became strained after Hill’s wife, Karen, became aware of their affair. Hill eventually moved on to Mazar’s character, Sandy, but their relationship began when his life was already in the downward spiral due to his drug abuse and trafficking. She had a number of super hot moments where audiences could definitely see the appeal in taking her on as a mistress but that quickly went downhill when she became completely strung out on cocaine and erratic in her behaviour. In the meantime, it’s interesting to see how Mazar looked during her younger years. She was a striking beauty with a great mix of ebony hair and porcelain skin.

7. Leslie Bega

via The Sopranos Wiki / HBO

When Leslie Bega was first introduced on The Sopranos, she was the half-Cuban/half-Italian beauty on the arm of Ralph Cifaretto. Since he had been known to beat strippers to death in the parking lot of Bada Bing, it was definitely interesting to see him with a sophisticated looking woman. She quickly grabbed the attention of Tony Soprano and after setting up a meeting about getting a portrait painted of his horse, the two wound up having sex at a hotel room. There was quite a bit of push and pull during the start of their relationship because Tony didn’t feel comfortable having Ralph’s sloppy seconds. Yet, further investigation proved that she didn’t actually have sex with Ralph, and therefore, it was alright in Tony’s eyes to continue having her as his mistress. There were some sexy scenes that involved Bega topless in the series and it seemed like she would be the woman that would truly grab his attention and keep it. Yet, a mishap involving a kitchen fire left her horribly disfigured and scarred. This might not have been the most diplomatic moment to break off the relationship but no one said Tony Soprano was very thoughtful when it came to other people’s issues.

6. Sharon Stone

via Aveleyman / Glamour

Sharon Stone had already solidified herself as one of Hollywood’s sexiest leading ladies when she portrayed Ginger McKenna in the 1995 film Casino. The film was released three shorts years after her infamous Basic Instinct role and fans were excited to see her act alongside heavy hitters like Robert De Niro and Joe Pesci. When she became romantically involved with De Niro’s character Sam “Ace” Rothstein, there were high hopes that she would change her hustling ways and settle down by his side. Yet, even when she was able to shake her old pimp boyfriend Lester Diamond, she fell into the arms of Rothstein’s friend Nicky Santoro. It’s interesting that she used to be close with Santoro’s wife and yet she had no problem becoming his mistress. The horrible love triangle that she created made a huge drama between Santoro and Rothstein and ultimately lead to Santoro’s death. Stone may not have looked very attractive towards the end of the film when her hair was more like something out of The Brady Bunch but she more than made up for it during the rest of the film when she really epitomized the glamorous mobster lifestyle.

5. Meg Steedle

via HBO

When Meg Steedle was first introduced as Lillian “Billie” Kent in the Boardwalk Empire series, she appeared to audiences as just a song and dance hire meant to liven up the party at Nucky and Margaret’s home. It was almost shocking when it was revealed that the pair was having a romantic relationship on the side. However, it was blatantly obvious that there were marital issues between Nucky and Margaret that had nothing to do with his philandering or partying ways. While Billy and Nucky’s former girlfriend, Lucy, had a lot in common in regards to their lifestyle and career choices, Billy was different in that she had some secrets of her own. It seemed that she was holding back from Nucky, even though he was all-in with his romantic feelings about her. Before she died, he wound up signing over a life insurance policy to her because he knew about the dangers of his criminal lifestyle and he wanted her to be taken care of in the event of his untimely death. Steedle did a phenomenal job at portraying her fun-loving character and her incredible sex appeal as the whimsical Billy Kent and was even able to pull off the blonde look without missing a step.

4. Emily Meade

via HawtCelebs / HBO

When James “Jimmy” Darmody was forced to travel to Chicago to work alongside Al Capone in the TV series, Boardwalk Empire, he left his entire life to start anew. It wasn’t exactly his choice to move away but he wound up making the best of it by climbing the ranks with Johnny Torrio. Although he was sending his money back to Angelina and their son, he was carrying on an affair with one of the prostitutes at Torrio’s brothels, Pearl. While it stands to reason that most of the men working at Torrio’s brothel probably had relations with some of the prostitutes on occasion, the relationship Jimmy had with Pearl was clearly more than just sex. The relationship was so close that Sheridan used Pearl to hurt Darmody. One of Sheridan’s men slashed her face and she ultimately committed suicide. Prior to her untimely end, Pearl was beautiful in a way that made audiences root for her and Jimmy to somehow make it work. Jimmy ultimately went back to Atlantic City and made a life with Angela but that situation didn’t exactly turn up roses either.

3. Gillian Darmody

via HBO

Throughout Gretchen Mol’s time on Boardwalk Empire as Gillian Darmody, she had used her sexuality as a mode to help her achieve her goals in life. Cultivating a relationship with the man that raped her and abandoned her and their child together was just one of the many men she had to try and use in order to get ahead. She did this again with Charlie “Lucky” Luciano and again with Gyp Rosetti. In the case of Gyp Rosetti, he was already married with older daughters. While Rosetti wasn’t a stranger to casual dalliances with women outside of his marriage, the relationship between him and Gillian Darmody was different. She had the uncanny ability to read what a man’s inner desires were in regards to his sexual preferences and she used this to try and get him to enact revenge on Nucky Thompson. However, she didn’t take into account that he might be an even worse person to deal with than Nucky. He practically took over her business and home and she wound up trying to kill him during a sexual encounter. Obviously, those were not a pair made for each other but it did give the audience some super sexy scenes of Gillian looking like a red-headed dominatrix set in the prohibition era.

2. Margot Bingham

via Pinterest / New York Daily News

When audiences first met Chalky White as a character in Boardwalk Empire, there wasn’t much backstory on him beyond the fact that he was helping Nucky win the African American voters. As the series progressed, audiences began to know more about his background and the details surrounding his life as a criminal bootlegger and underling of Nucky Thompson. For one thing, he was not educated and couldn’t even read. Yet, his wife and children were educated and living a lifestyle that could be afforded a family with the stellar income that he provided through his illegal endeavours. After feeling like an outsider, even within his own home, Chalky began having a relationship with the singer, Daughter Maitland. He seemed to be able to be more of his genuine self with her and the affair that they carried on was more than just sexual in nature. They seemed to have a true connection, which he couldn’t have with his wife. The actress that played Daughter Maitland is actually an acclaimed Broadway singer/songwriter by the name of Margot Bingham. Not only did she do a fantastic job in conveying the character in this period drama but she exuded major sex appeal that only she could deliver on stage.

1. Sarah Shahi

via HBO

Throughout The Sopranos series, audiences had seen Chris Moltisanti cheat on his girlfriend Adriana La Cerva a number of times. There was a time when Paulie actually caught him having sex with a prostitute, to which Moltisanti replied that he never pays for it. Moltisanti also carried on an affair with his cousin’s fiancée in the episode, “D-Girl.” Yet, everyone just assumed that these might just be isolated instances and perhaps he truly did love Adriana enough to be faithful to only her if she hadn’t died at the hands of Silvio Dante. Yet, viewers learned that Moltisanti actually had a “goomar” by the name of Sonya Aragon, played by Sarah Shahi. She was living in Las Vegas and Tony flew out there and was the one to inform her that Moltisanti had died in a car accident. Tony and Aragon wound up having sex and going to the dessert and taking peyote together. While her appearance on the series was fleeting, she made quite an impression on fans hoping to figure out who was that beautiful woman during the episode, “Kennedy and Heidi.”

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