The Sopranos

The Sopranos Actors With Real Life Gangster Connections

A few of the actors who appeared in The Sopranos were either directly associated with gangster families or had relations with individuals who were.

HBO’s groundbreaking The Sopranos was lauded for being so realistic, perhaps because a number of its actors were linked to mob families and criminal activity in real life. The Sopranos was created by David Chase and aired from 1999 to 2007, with the goal of accurately portraying life within organized crime. The show was a huge success, drawing in large audiences and receiving outstanding reviews from critics, with many calling it the greatest television series ever created. The show also received numerous awards, including the Primetime Emmy Award for Outstanding Drama Series and the American Film Institutes’ Drama Series of the Year Award

The Sopranos followed New Jersey mobster Tony Soprano as he attempted to juggle the life of a mob boss along with the role of husband and father. Due to his lifestyle, Tony constantly found himself in danger from other rival families and even members of his own family, unsurprisingly leading to a high amount of stress and even panic attacks. Because of this, Tony Soprano attended therapy sessions, allowing the show to explore the difficulties of being a leader of a criminal organization while also retaining a steady family life which often intermixed, such as the romance between Tony’s wife Carmela and The Sopranos‘ Furio Giunta.

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Being considered one of the greatest television shows of all time, The Sopranos offered a remarkable portrayal of life within organized crime. One aspect of the show that made it so great was the acting, as many of the actors in The Sopranos offered incredible performances as gang members and criminals, allowing the audience to become fully immersed in the crime world of The Sopranos. Interestingly, a few of the actors who appeared in the show were directly associated with or linked to mob families and criminal activity in the real world.

Tony Darrow

Larry Barese during a meeting for capos inside the Bing

Tony Borgese, who had the stage name Tony Darrow, played the character of Larry Barese in The Sopranos. Tony had a father who was in and out of prison throughout his life. When he was still young, Borgese became friends with John Gotti and Paul Vario. Vario was the son of a local mobster in Brooklyn and helped Borgese get a job in a nightclub. In 2011, Tony Borgese was arrested for allegedly hiring members of the Gambino family to beat a man who owed him a debt. Tony Borgese eventually pleaded guilty and was originally sentenced to three years in prison, but instead was sentenced to six years of house arrest and a two-year probation.

Michael Squicciarini

Frank pointing a finger at the Bada Bing in The Sopranos

Michael Squicciarini, who played the character Frank Cippolina, only appeared in a few episodes in The Sopranos season 2Squicciarini spent many years in and out of prison for several crimes, including five years in prison for aggravated assault. Notably, he was associated with the DeCavalcante Family, which was one of the original inspirations for The Sopranos.

Unfortunately, Squicciarini passed away in 2001. But in 2002, he was posthumously implicated in the murder of drug dealer Ralph Hernandez. Squicciarini was accused of luring Hernandez to a club in Brooklyn so that Hernandez could be shot down by DeCavalcante capo Joseph Conigliaro. Witnesses spotted Squicciarini while watching The Sopranos, and claimed that he may have assisted in moving and disposing of the body of Ralph Hernandez.

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Tony Sirico

Paulie Walnuts pointing his finger in The Sopranos

Also from Brooklyn, Tony Sirico played the role of Paulie Gualtieri in The Sopranos. During the ’60s and ’70s, Sirico worked for the Colombo crime family under Carmine Persico and spent a lot of time in and out of jail. He was arrested 28 times for a wide variety of crimes, including weapons possession and robbery. It was during one of his arrests in prison that Sirico discovered his passion for acting, which led to his appearances in many movies and shows including Goodfellas and The Sopranos.

Vincent Pastore

Salvatore "Big Pussy" Bonpensiero reappears in New Jersey after going into hiding in South America The Sopranos

Vincent Pastore took on the role of Salvatore Bonpensiero in The Sopranos, one of the main characters of the show. While not directly associated with the life of organized crime, Pastore has family members who were associated with gangster families, including an uncle and a couple of cousins. Pastore managed to stay away from the life, but he was close enough to it that he had firsthand knowledge of how it worked.

Tony Lip

Carmine plays goldf with Tony in Sopranos

Frank Anthony Vallelonga, with the stage name Tony Lip, had a recurring role in The Sopranos as Carmine Lupertazzi. Lip also appeared in Goodfellas and The Godfather. While not necessarily associated with the life of organized crime, Vallelonga spent a considerable amount of time as a bouncer at the Copacabana Club in New York. During the ’60s, he also spent some time as a bodyguard for the classical pianist Don Shirley, during Shirley’s tour of the states in the Deep South.

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