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From Tony Montana to Tony Soprano: Infamous Mobsters Who Inspired Famous Characters in Movies and TV

real life gangsters film counterparts pp
Source: MEGA

Mar. 27 2024, Published 4:03 p.m. ET

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We've all seen them. Maybe even quoted some of their famous lines. 

Movie mobsters can seem larger than life and always once step ahead of the law. They develop complex plots to help their enterprise and seem to operate in a world many of us never experience. 

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But, did you know that often the characters on screen or based on actual people? Here are some examples of famous mobsters on TV and in movies and their real-life counterparts. 

TONY SOPRANO — VINCENT “VINNY OCEAN” PALERMO

soprano_palermo pic
Source: NYD News FIle Photo; MEGA

Actor James Gandolfini played the character Tony Soprano in the hit HBO Series “The Sopranos.” Italian American mob boss Vincent “Vinny Ocean” Palermo was the inspiration behind Tony’s vindictive nature.

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Vincent has been an FBI informant since 1999 due to his involvement in the takedown of the DeCavalcanter family. “Vinny Ocean” became a part of the mob after he married the niece of Sam “Sam the Plumber” DeCavalcante during the 1960s. Vincent rose in the mob ranks after his involvement in the murder of Fred Weiss, a suspected informant wanted dead by John Gotti, another infamous crime boss at the time.

After he was arrested in 1999 for his connection to Weiss’s murder, he turned into an informant. Vincent’s testimony during his trial brought down the DeCavalcante family, which was the only homegrown organized crime family in New Jersey at the time, according to the New York Daily News.

Since the commencement of the trials, Vincent lives a private life with his family, and owns several clubs in Houston. 

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VITO CORLEONE — FRANK COSTELLO

Vito Corleone is a character from the 1969 novel “The Godfather” by Mario Puzo and the movie trilogy “The Godfather” by Francis Ford Coppola. Mobster Frank Costello inspired the character Corleone, which is played by the late Marlon Brando.

Part of the infamous Luciano crime family, Italian American Costello took over as mob boss when Charles “Lucky” Luciano received a lengthy prison sentence for operating a prostitution ring. 

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During his reign, Costello served as an acting boss for the family for over 20 years until his attempted assassination by Vito Genovese. After surviving the attack, Costello handed control of the Luciano family to Genovese, according to the FBI.

In February 1973, Costello died from a heart attack at a Manhattan Hospital, at the age of 82.

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TONY MONTANA — AL CAPONE

al caponetony montana pic
Source: MEGA

The movie “Scarface” depicted the character Tony Montana, played by actor Al Pacino which was inspired by considerably the most famous gangster in history, Alphonse Gabriel “Al Capone” Capone

Al Capone assumed the boss position of the Chicago Outfit, an organized crime family in Chicago that is still running since its establishment in 1910.

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Capone is famously known for his involvement in the St. Valentine’s Day Massacre on Feb. 14, 1929, as it is considered to be the event that initiated gun violence in Chicago gangs. The bloody massacre occurred after Capone ordered a hit on his rival, George “Bugs” Moran and his associates. 

Capone continued his reign as a top Chicago mob boss for over a decade until his crimes got into trouble with the FBI. Capone had several stints in prison for charges relating to prohibition tax evasion charges. 

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On Nov. 16, 1939, Capone left prison for the last time after serving more than seven years, according to the FBI.

Capone died from natural causes related to stroke and pneumonia on Jan. 25, 1947.

JIMMY “THE GENT” CONWAY — JAMES BURKE

james burke jimmy conway pic
Source: MEGA, Paramount Pictures

The talented actor Robert De Niro played the role of Jimmy “The Gent” Conway in the 1990 film “Goodfellas,” which was inspired by real-life American gangster, James “Jimmy the Gent” Burke

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Alongside the film, author Nicholas Pileggi wrote about Burke in his novel “Wiseguy.”

It is alleged that Burke led the 1978 Lufthansa theft. The robbery happened on Dec. 11, 1978, when Burke’s team infiltrated one of Kennedy International Airport’s cargo terminals to take $5.8 million in untraceable American money. 

As of today, the money has never been found, so Burke was never charged for the crime, according to the New York Times

In April 1996, Burke died from cancer at the Rosewell Park Cancer Institute at the age of 64.

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