Frank Sinatra has the best documented ties to the Mafia of any celebrity: the FBI followed him for almost five decades. This list covers famous people whose connections to organized crime are on the public record, either through documented friendships or through the mob roles that defined their careers. Mentions here reflect public reporting and screen work, not accusations.
| Rank | Name | Connection |
|---|---|---|
| 1 | Frank Sinatra | Almost five decades of FBI files |
| 2 | James Caan | Close family friend of a Colombo family figure |
| 3 | Jerry Orbach | Linked to gangster Joey Gallo |
| 4 | Robert De Niro | Played mobsters across five decades |
| 5 | Joe Pesci | Mob roles in Goodfellas, Casino and The Irishman |
| 6 | Al Pacino | The Godfather, Scarface and Donnie Brasco |
| 7 | Marlon Brando | The original Godfather |
| 8 | Ray Liotta | Henry Hill in Goodfellas |
| 9 | James Gandolfini | Tony Soprano |
| 10 | Lorraine Bracco | From Goodfellas to The Sopranos |
1. Frank Sinatra
The singer and actor, born in Hoboken in 1915 and who died in 1998, is the best documented case. The FBI kept files on him totaling 2,403 pages and surveilled him for almost five decades, starting in the 1940s.
Sinatra was reported to be a good friend of mobster Sam Giancana. He denied any mob involvement, calling reports that he associated with criminals a vicious lie.
2. James Caan
The Godfather star, who died in 2022, played Sonny Corleone and was open about his friendships with New York wiseguys. His friend Andrew “Andy Mush” Russo, reported to be a Colombo family figure, was godfather to Caan’s son Scott. Caan is also reported to have socialized with Colombo boss Carmine Persico during the making of The Godfather.
3. Jerry Orbach
The Broadway and TV actor, who died in 2004, played Kid Sally Palumbo, a character loosely based on Joey Gallo, in the 1971 comedy The Gang That Couldn’t Shoot Straight.
Orbach and his wife are reported to have joined Gallo’s party at the Copacabana on the night Gallo was killed in 1972.
4. Robert De Niro
De Niro, 83, won an Oscar for playing young Vito Corleone in The Godfather Part II (1974). He went on to play Jimmy Conway in Goodfellas (1990), Sam Rothstein in Casino (1995) and starred in The Irishman (2019).
His ties to the Mafia are professional: he has played gangsters in everything from drama to the comedy Analyze This (1999).
5. Joe Pesci
Pesci won the Oscar for Best Supporting Actor for playing Tommy DeVito in Goodfellas (1990). He then played Nicky Santoro in Casino (1995).
He came out of semi-retirement to play Russell Bufalino in The Irishman (2019).
6. Al Pacino
Pacino played Michael Corleone in The Godfather films, in 1972. He later played Tony Montana in Scarface (1983) and the real-life Mafia soldier Lefty Ruggiero in Donnie Brasco (1997).
Few actors have defined Mafia cinema as long as he has.
7. Marlon Brando
Brando, who died in 2004, played Vito Corleone in The Godfather (1972) and won the Oscar for Best Actor, which he declined to accept.
His Vito Corleone remains the reference point for later screen mob bosses.
8. Ray Liotta
Liotta, who died in 2022, played the real-life mob associate Henry Hill in Goodfellas (1990), the role that made his name.
The film won an Academy Award.
9. James Gandolfini
Gandolfini, who died in 2013, played mob boss Tony Soprano in The Sopranos from 1999 to 2007.
He played the role throughout all six seasons of the series.
10. Lorraine Bracco
Bracco earned an Oscar nomination for Best Supporting Actress for playing Karen Hill in Goodfellas (1990).
She later played therapist Dr. Jennifer Melfi, who treated Tony Soprano, in The Sopranos.
FAQ
Which celebrity has the best documented ties to the Mafia?
Frank Sinatra. The FBI kept files on him totaling 2,403 pages and surveilled him for almost five decades. He denied any involvement.
Why was James Caan linked to the Colombo family?
His close friend Andrew “Andy Mush” Russo, reported to be a Colombo family figure, was godfather to his son Scott, and Caan is reported to have socialized with Colombo boss Carmine Persico during the making of The Godfather.
Was Jerry Orbach connected to Joey Gallo?
Yes. Orbach played a character loosely based on Gallo in a 1971 film, and he and his wife are reported to have joined Gallo’s party on the night Gallo was killed in 1972.
Are Robert De Niro’s mob ties real?
They are professional. He has played mobsters in The Godfather Part II, Goodfellas, Casino and The Irishman.
Why do so many actors appear on a list about the Mafia?
Mob movies and shows, from The Godfather to The Sopranos, made stars of their casts, and several of the actors spent time with real people while preparing.
How we put this list together
We included people whose connections to organized crime are described in public records, interviews and film history, and we left out unproven rumors. Each entry states what is documented and, where it applies, that the person denied it.
Last updated: October 2026.
