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Hollywood and organized crime go way back. The two entities have been in a cozy and subtle (and sometimes not-so-subtle) relationship of sorts for decades. For one, Hollywood loves to produce mafia movies and promote tough-guy mafia characters. The film industry makes the mob look glamorous to many, and the storylines of mob hits, family ties, and dramatic gangster acts take a front seat on the silver screen.

But behind the scenes, the industry has long been rumored to have a host of mafia connections, too. On the surface, it makes sense. Celebrities have money, power, and fame—and plenty of social influence. Why wouldn’t organized crime want a piece of that action? Popularity is paramount in the movie business, and mafia ties have long been thought to be working behind the scenes, laundering money and courting connections.

The relationships go back way further than you might imagine, too. In this list, we’ll take a look at ten world-famous Hollywood stars who supposedly got mixed up with the mob. Some of these celebrities were said to have deep, lasting connections to the crime syndicate throughout their careers. Others got involved in unlikely, sketchy, and even nearly-deadly ways. But they all came away with rumored relationships that are still being talked about—sometimes decades later. This is the real story behind ten Hollywood hotshots and their links to the mob…

Related: 10 American Mobsters Who Were Not Italian Americans

10 Frank Sinatra

Let’s start with the most-talked-about mob pal in all of Hollywood, shall we? A big part of Frank Sinatra’s lasting legacy and public legend centers on his supposed mafia connections. It’s not just talk, either. The FBI was so suspicious about it that they documented Old Blue Eyes’ movements and relationships for years before his death. The singer had known friendships with many high-profile mobsters, including Sam Giancana—the longtime head of the Chicago Mafia.

All of Hollywood and much of the public knew about Sinatra’s supposed mob hangouts during his life, too. Heck, the infamous character Johnny Fontane in The Godfather is said to be based on Sinatra. You know the one: Fontane goes to Don Corleone begging for help in landing a film role. The novel’s author, Mario Puzo, forever denied that Fontane was based on Sinatra, but there has been little question about that in the minds of moviegoers.

For Sinatra’s part, he denied for years that he was ever connected with unsavory characters. He even leveraged the accusations against him in his favor at points. For one, he claimed the mob allegations were based on anti-Italian racism. Critics, Frank said, had picked up on his name and heritage and were using the mafia to disparage his good name. So, what was really going on?

As modern-day historians have come to consider, it’s likely that mobsters simply really loved Sinatra, regardless of how he felt about them. After all, his upbringing and the facts of his life and career were extremely attractive to the Italian and Italian-American men who grew up during that generation. Thus, it’s at least likely—if not outright true—that mobsters gravitated to Sinatra rather than the other way around.

Smart enough not to spurn their support, he allowed them in his orbit and was thus connected to them for years. After all, it might have been worse to ignore them. But in the end, it got Old Blue Eyes a big FBI file and a lot of unwanted attention from law enforcement.[1]

9 James Caan

James Caan made his living on the silver screen playing wise guys, tough guys, aggressive guys, and violent guys. And in real life, associates have claimed both before and after his 2022 death, the actor was all those things and more. Caan memorably played the mobster Sonny Corleone in The Godfather, and he did a bang-up job in the role. But according to some mobsters themselves, that’s because it wasn’t acting.

Caan, they claim, was “connected.” None other than Sammy “The Bull” Gravano once asserted Caan was heavily involved in the Colombo crime family. Per that iconic mafioso, Caan had officially been termed to be an “associate” by the family. That’s a specific mafia rank bestowed upon trusted non-Italians who ingratiate themselves into mob business. As the story goes, Caan was so deep into mafia ties that he supposedly even personally asked Joe Colombo for permission to play Sonny on the big screen.

But is all that actually true, or was Gravano simply trying to glorify the mafia by connecting the real-life underworld to one of the greatest movies ever made? Well, Caan himself publicly admitted Colombo family connections at various points in his life. For one, he copped to being closely linked to Colombo streetman Andrew Russo via longtime family connections. Caan was even named the (literal) godfather of Russo’s son Scott. There are even allegations Caan used his mafia connections to put pressure on producers to cast him for coveted movie roles.

However, perhaps the most amazing allegation involves another superstar. According to Caan’s own obituary after his death in July 2022, the Hollywood star supposedly once asked a mob associate to kill Joe Pesci over an $8,000 debt. Thankfully for Pesci—and all of his fans—that hit was never carried out. But if true, it would suggest some serious mafia moves running through Caan’s life and career.[2]

8 George Raft

George Raft was a star long before many of the rest on this list. And his mafia ties allegedly run deeper than most, too. The big star-making role that pushed Raft into prominence was playing Rinaldo in the 1932 classic movie Scarface. In that movie, Raft was such a good mobster that for years after, it was thought his on-screen portrayal actually changed how real mafiosos behaved in actual life. That’s pretty iconic! But if Raft knew anything about how to be a gangster on screen, it was because of his own upbringing.

The Hollywood star grew up in a tough part of New York City. When he was still a kid, he worked the streets for infamous Irish Mafia boss Owney Madden. He even enjoyed close friendships with Las Vegas mobsters Bugsy Siegel and Meyer Lansky throughout his adult life. It wasn’t all talk, either; Raft was once banned from entering Britain after taking a transatlantic flight because London officials were worried about his supposed mob connections.

Much like Sinatra above, Raft’s mafia connections were likely more relational than active. That is, he grew up around some tough guys and remained close with other tough guys all his life—without taking part in any mob activities himself. The relationships helped his career, though. Raft could play a tough guy on screen as convincingly as anybody in the business, and there’s no question that came about because of his personal past.

And he did do at least one good thing with his mob ties: Legend has it Raft once stopped planned assassinations of actors James Cagney and Gary Cooper after they supposedly angered mafia dons during their own long careers. That alone would seem to be quite an achievement for the silver screen star. Using his mob meets for good—sort of.[3]

7 Lana Turner

For decades through the middle of Hollywood’s Golden Age, Lana Turner was one of Tinseltown’s biggest stars. Her life off screen was extremely dramatic, too. She was married seven times during her day. And she supposedly had affairs with several of Hollywood’s biggest male stars, too. But it was her tumultuous relationship with mafioso Johnny Stompanato that really set things off as far as we’re concerned here.

Stompanato was closely linked to mob boss Mickey Cohen during his day. Johnny was violent, unpredictable, and said to be extremely well-connected in the world of organized crime. After a while together, Turner began to tire of the roller coaster relationship. She tried to end the affair multiple times but was rebuffed by Stompanato’s seemingly random and unsettling fits of anger. He even supposedly threatened her with mafia-ordered violence if she ever left him.

But it all came to a head on April 4, 1958. On that day, Turner and Stompanato were heard getting into a loud screaming match. The two fought often, but this time, the stakes were heightened, and the emotion was higher than it had seemingly ever been before. At the pinnacle of the fight, the unthinkable occurred: Stompanato was stabbed to death. When police arrived to process the scene, Turner told them that her daughter Cheryl Crane—who was just 14 years old at the time—had rushed into the room and killed the mobster.

Crane, the Hollywood star explained, was simply doing what she felt was necessary to protect her mother from being hurt. That may be true, and prosecutors liked the story so much that they considered it a justifiable homicide and moved on. But forever after, rumors have swirled that Stompanato’s mob ties had something more to do with his stabbing, and Turner was allegedly more deeply involved than has ever been revealed. Creepy![4]

6 Bing Crosby

Bing Crosby had one of the cleanest and most pristine public images in all of Hollywood. He was known to be a down-to-earth average Joe with the voice of a god. He was clean cut, handsome, and seemingly sweet—accessible to all but also venerated by fans. Sadly, the real-life story behind the scenes was far different.

For one, Crosby was a heavy drinker when he wasn’t working. He was also allegedly an abusive father who came down very hard physically (and emotionally) on his children and others in his personal life. And he was a big fan of gambling. Publicly, this manifested itself in a love of horse racing. But privately, he sought out significant high-stakes games and even reportedly came across some terrifying moments involving organized crime.

Once, in 1929, Crosby got drunk one night while out at a party. Somehow, when he woke up the next morning, he was in a house surrounded by gangsters. Alarmed, he walked into a bathroom to clean himself up. As soon as he left, another group of toughs walked in and shot up the room he’d only left a few minutes before. And that was far from his only close call. According to a 1999 report, Bing once paid $10,000 to a mobster in order to save his own life after his gambling debts spiraled out of control.

The crooner’s mafia ties were so tight that the FBI decided to launch a full investigation into what he knew. Crosby, after all, had been playing golf and drinking with many of the country’s toughest mobsters for years. And his gambling debts only further entrenched the star’s need to associate with reputed mobsters if only to protect himself from harm.[5]

5 Debbie Reynolds

If you know anything about Debbie Reynolds’s career, you are probably shocked to see her name on this list. Heck, her career is a testament to the exact opposite of mafia ties. But she was mixed up in it, too. And unlike many on this list, she may not have known exactly how complex and intricate the situation was at its zenith. Reynolds’ second husband was a man named Harry Karl. He was the owner of the Karl’s Shoe brand.

Prior to marrying Debbie, he had been briefly married to a woman named Joan Cohn—the widow of former Columbia Pictures leader Harry Cohn. Karl’s marriage to Joan lasted only a few weeks, which was strange in the 1950s. The best the FBI and LAPD could figure was that the marriage was arranged by organized crime bosses to hide who some of the true investors in Columbia were. Harry was sent in to “marry” Joan, at which point he could control the Cohn estate and pay back the mob without a telling paper trail. Or something.

Then, in 1960, after Karl’s quickie marriage with Joan ended, he got hitched to Reynolds. These two did appear to have married for love, or some approximation of it. But even in that relationship, those around Reynolds dealt in secrecy. After Debbie and Karl said, “I do,” Karl transferred a Los Angeles mansion’s deed to a man named Sidney Korshak. Sidney was a powerful attorney who was reputed to have deep ties to organized crime. Not long after the inexplicable transfer, Sidney then negotiated a surprisingly large salary for Reynolds to make her live performing debut in Las Vegas—a city often said to be tightly controlled by the mafia.

Then, a few years later, Reynolds’s business managers struck again. They got her mixed up in a business creating Scopitone films. These were primitive music videos played on jukeboxes in the late 1960s. That company went out of business in 1969 after it was tapped by the FBI as being a front for laundering mafia money. Cops didn’t link Reynolds herself to the backroom dealings, but the fact that her name popped up again was certainly a head-scratcher considering her public persona.[6]

4 Tony Bennett

Like many professional and very masculine crooners before him, Tony Bennett has long been rumored to hold attachments to organized crime. It’s not just Bennett’s ties to men like Frank Sinatra that make people assume he’s “connected.” It’s also his long, steady career in Las Vegas as the town grew via mob development money and coordinated casino interests. And it’s a rumor bandied about by Bennett’s own biographer.

David Evanier, who penned Bennett’s biography, offered a remarkably deep look at the star’s upbringing in the book. In it, he asserted the smooth singer actually got his start decades ago with the help of mob money. To hear Evanier tell it, Tony Bennett supposedly served as an associate of organized crime syndicates for many years in an outsider’s role similar to what James Caan lived through.

But Bennett wasn’t fated to merely live out his associate stature like that. In the late 1970s and early 1980s, he fell into a deep depression. He was using drugs heavily at the time, too, and the combination proved to be bad for his mental and physical health. Right around that same time, while vulnerable in multiple ways, Bennett reportedly started seeing a woman who was known around Sin City as the girlfriend of mafioso Anthony Spilotro.

Unsurprisingly, Spilotro didn’t care for the singer making moves on his girl. So he went to confront Bennett about the ill-fated relationship. But here’s where the crooner got very, very lucky: Instead of killing him, like the mobster probably wanted to, Spilotro simply struck Bennett on the top of the head with a phone book. It’s a strange attack, but it worked. Not only did it knock the singer unconscious, but it also moved him to drop the girl. And, even better for Bennett, it seemed to knock a bit of sense into him, too. A few weeks later, he checked into rehab and got clean for good.[7]

3 Marilyn Monroe

Marilyn Monroe is an iconic sex symbol who has withstood the test of time unlike any other. The downslope of her career was a tragic one, though. She was consumed by the awful, darker aspects of the fame that had so quickly risen her to the top years earlier. And while the official story is that Monroe died of a self-administered barbiturate overdose in August 1962, skeptics have long held that there was a more nefarious cause behind her untimely passing.

It all starts with the actor Gianni Russo. He played Carlo in The Godfather, and he was thought during his life to be connected to organized crime operations. He even worked for the legendary mobster Frank Costello when he was a very young man. As part of that work, Russo later claimed to have heard that Monroe was killed by shadowy mafia henchmen.

As that tall tale goes, Marilyn was supposedly used by mafia overlords to get close to John F. Kennedy and his brother, Robert Kennedy. The mob wanted to use Monroe to get key information out of John both before and during his rise to the presidency. Then, as Robert would soon push hard for the presidency a few years later, the mob was hoping to lean on him for connections and favors, too.

Monroe, the story goes, had grown tired of mob involvement in her personal life. So she was said to be about to go public with her story about the mafia when she suddenly died. The controversy goes beyond just supposition, though. Many now say Monroe’s apartment was bugged, and mafia bosses—and/or American intelligence operators—were listening closely.

Monroe was also thought to have visited notorious Chicago mob boss Sam Giancana just a few days before she wound up dead at her Los Angeles home. Giancana was allegedly said to have asked Marilyn not to speak about her closeness to John Kennedy lest the mob lose their leverage over him. It’s unclear what would have come from that meeting, though, since the star-slash-socialite was found dead just a few days later.[8]

2 Wayne Newton

Few people have as squeaky-clean of a public persona as Wayne Newton. The entertainer rose to fame in Las Vegas right as the city was reimagining itself as a more family-friendly road trip spot than it had been in its past. Newton rode that wave to stardom in town, and it even transcended from his own live shows to television spots and other more national kinds of fame. But behind the scenes, Vegas insiders were wondering about Newton’s supposedly shady connections to organized crime. And when word first got out that the singer could allegedly be attached to some type of syndicate, all hell nearly broke loose.

It all started with Newton’s turn as a part owner of the Aladdin Casino. The casino management’s decision to add Newton to its ownership group was a strange one, but Vegas insiders began wondering if it wasn’t very purposeful. After all, Newton had no criminal record and no public criminal ties. Thus, he was “clean” enough to operate a gaming license in the state of Nevada, unlike some of his allegedly more “connected” pals.

One of those pals was a man named Guido Penosi. He and Newton had long had a friendship—one Newton himself admitted to—but Vegas cops and local newspaper reporters were suspicious of it because of Penosi’s alleged mob ties. After word about Newton and Penosi’s friendship first got out in the media, Newton filed a lawsuit against NBC News. In his suit, the singer claimed he feared for his own safety because the reports made it seem like he was cooperating with law enforcement officers in their pursuit of mafia bosses.

Newton himself said he wanted no part of either side—he merely wanted to entertain tourists. Initially, he was awarded $19 million in damages by a Nevada jury, but an appeals court later struck down the ruling. Regardless, Nevada gaming officials stuck by their story about being concerned with Newton’s alleged connection to Penosi. Now, whatever the truth is, the world may never know it.[9]

1 Jerry Orbach

You may know Jerry Orbach from his stint as a detective on Law & Order, or if you’re a little bit older, you surely remember his star turn in Dirty Dancing. But his entertainment career went back decades before that, all the way to the 1950s. And rumors about his mob ties started up not long after he first rose to fame. In 1971, Orbach was cast as Salvatore “Kid Sally” Palumbo in a comedy movie called The Gang That Couldn’t Shoot Straight. The film was about a bunch of hapless mobsters, and Orbach’s character was based on a real-life mafioso named Joe Gallo.

Not surprisingly, Gallo—who was a ranking member of the Profaci crime family in New York City—was displeased that an entire movie was made about how he was supposedly incompetent. So he set up a meeting with Orbach to, um, talk about the film. Amazingly, Gallo didn’t harm Orbach. Instead, the mobster and the actor hit it off and became fast friends.

Then, less than a year later, Gallo was murdered. The mobster had been eating at Umberto’s Clam House in New York City’s Little Italy in April 1972 when he was gunned down in what appeared to be a hit by another crime family. Orbach and his wife had been hanging out with Gallo earlier in the evening on that fateful day; the group even watched a Don Rickles comedy set together.

Some rumors even contend that Orbach allegedly joined Gallo at that final dinner. That would have made Orbach a witness to the killing and, thus, a very critical party for cops to interrogate. But if he did see it go down, the longtime actor never spoke a word of it to anyone. He refused to cooperate with police, and for the rest of his life, he never so much as spoke publicly about Gallo. When Orbach died in 2004, he took whatever mafia secrets he had to the grave with him.[10]

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