5 Sopranos Cast Members With Real Gang Ties (Allegedly)

There is a case to be made that The Sopranos is arguably the greatest show to ever grace television screens. It’s a realistic look at mob life through the eyes of its therapy-visiting main character, Tony Soprano (James Gandolfini). Not only did The Sopranos examine what life inside organized crime was like, but it also made the characters so identifiable because of the problems they face.

There is enough existentialism to go around for six lengthy seasons for any viewer to go down a wormhole with. Even if you’re not a fan of mob movies and shows, The Sopranos always delivered night after night during its run from 1999 to 2007.

The Sopranos

Release Date
January 10, 1999



If you happen to be a fan of the subgenre that centers on tales of the mafia, you’ll know that there are always a lot of consultants on film and television sets that assist in making the material more realistic. The Sopranos did just that; They even had people with alleged mob ties play major parts in the show. Here are five cast members who were believed to be part of La Cosa Nostra that appeared on the show. Some are more frequent than others. Stream The Sopranos on HBO.

5 Tony Lip

Frank Anthony Vallelonga, otherwise known by his stage name, Tony Lip, was a featured character throughout The Sopranos. His character was Carmine Lupertazzi, the boss of one of the five families in New York City who has a long-standing relationship with the Soprano family in New Jersey.

Lip’s Crime Connections

There is a reason why this article says “allegedly” in its title, as Tony Lip has never been directly connected to any organized activity that put him behind bars. However, while he was a struggling actor in New York in the 1960s, he was a bouncer at the Copacabana Club in New York. A place where many wise guys liked to hang out. One would think that Lip had seen some mafia activity in his time. Let’s not point any fingers here, though.

Related: 18 Greatest Gangster Movies Made Outside the U.S.

4 Vincent Pastore

Vincent Pastore plays one of the most iconic characters in the show, Salvatore Bonpensiro, otherwise known as Big P*ssy. His appearance on the show made a long-felt impact, lasting only two seasons before having to sleep with the fishes due to being an FBI informant against the crew he ran with. Pastore has also played in other mob films, like Goodfellas, The Family, and Mickey Blue Eyes.

Pastore’s Mob Ties

Pastore, once upon a time, could have fallen into a life of organized crime, but stayed away from it. He makes the list because he had family members who were connected to the mafia.

It is believed that Pastore had an uncle and some cousins who worked directly with the mob; he had distanced himself from that kind of life. His knowledge of it has potentially helped him in his acting career. He is one of the actors who get typecast in mob films, but stands out among the pack.

3 Michael Squicciarini

Michael Squicciarini has a brief, nearly forgettable role in Season 2 of The Sopranos as a tough guy bouncer at the nightclub the crew all hangs out at. Michael plays the character Frank Cippolina, but was eventually written out of the show due to his untimely death in 2001.

Squicciarini Was Posthumously Implicated in a Murder

Maybe due to his brief stint on the show, Squicciarini does not top the list, but let it be known that he was the real deal in terms of being a connected member of the underworld of the mafia. He had been in and out of prison for many different reasons. He did a bid for five years for aggravated assault.

Squicciarini was associated with the DeCavalcante family, the family that was the inspiration for The Sopranos. After his death in 2001, he was connected to the murder of a drug dealer in Brooklyn. Many witnesses spotted him on the show and connected him to dumping the body of said drug dealer after he had been killed.

2 Tony Darrow

Tony Darrow is the stage name of Tony Borgese. He played Larry Barese on The Sopranos, a reoccurring character on the show who is a Capo of the Barese crew, a group that is part of the DiMeo crime family. Many may remember Darrow from his brief role in Goodfellas as the club owner who went into business with Paulie but had to sell it all over to him, and it ended up burning down.

Darrow’s Gambino Crime Family Ties

In 2011, Tony Darrow got into some legal trouble as he was arrested for allegedly hiring members of the Gambino crime family to beat a man who owed him a debt.

Darrow was convicted and sentenced to three years in prison, but he would end up dodging jail time, and be under house arrest for six years, and have to serve a two-year probationary period after the house arrest ended.

Related: 15 Best Mafia and Gangster Movies Ever Made

1 Tony Sirico

The late Tony Sirico gave us one of the greatest and most eccentric characters in The Sopranos. Sirico played Paulie Gualtieri, aka Paulie Walnuts. His one-liners, off-beat humor, and complicated relationship with Christopher Moltisanti made up great secondary plot lines throughout the show.

Sirico and the Colombo Crime Family

Sirico lived a fulfilling life, but who knows if it could have been cut short back in the 1960s and 1970s. Sirico ran with one of the five families when he was younger, the Colombo family.

He was arrested more than 20 times, and in jail, he discovered his passion for acting. So, eventually, he would turn his life around and leave behind the excessive life of crime. You can spot Sirico in films like Goodfellas, Copland, and 1996’s Gotti, prior to being in The Sopranos.


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