When Frank Sinatra ordered a hit on a comedian for making fun of him: “Boys, that’s enough”
The biggest stars usually have the biggest egos, which means, by extension, they’ve often got the thinnest skin. Frank Sinatra may have been lauded as one of his era’s coolest and most effortlessly charismatic entertainers, but he didn’t take too kindly to being mocked by a stand-up comedian.
As has been the case since the first joke in human history was made, the most famous and well-known people make prime targets. As long as the material is strong enough, poking fun at a person that everyone in the audience knows by name and reputation is among the easiest ways to get a laugh.
That served as the backdrop to a particularly dicey set from Jackie Mason, who got more than he bargained for when he crossed the line and attacked Sinatra’s personal life. Shortly after ‘Ol’ Blue Eyes’ married Mia Farrow in 1966 when he was 50 and she was 21, the comic sensed an opportunity.
The downside was that Mason decided to incorporate the joke into his act when he was performing in Las Vegas, a known Sinatra stronghold that he frequented with both his Hollywood friends and those who may or may not have been deeply embedded in the organised crime syndicates that the actor and singer may or may not have been eminently friendly with.
Two decades later, Mason’s sins had yet to be forgiven. After catching wind that he’d be back onstage in Vegas, Sinatra and his associates turned up and began heckling to try and throw the comedian off his rhythm before vacating the premises. Later that night, three bullets were fired into his hotel room and ended up lodged in the bed where he’d recently been sitting.
Did that stop Mason from cracking Sinatra gags? No, quite the opposite. “I have no idea who it was who tried to shoot me,” he regaled another captive audience. “After the shots were fired, all I heard was someone singing, ‘Doobie, doobie, doo.’ While he couldn’t exactly come out and say it was the Academy Award winner who’d tried to have him killed, the allusion was strong enough to get him in more trouble.
Returning to the Sinatra well yet again, Mason continued needling ‘Ol’ Blue Eyes’ from afar by adding new material into his set that included references to the alleged lifts in his shoes he used to make himself appear taller and the toupee he’d never be spotted in public without.
Having pissed him off again, Mason was once more the recipient of mysterious violence. This time, he was brutalised by two assailants who broke his nose and shattered his jaw with brass knuckles, which left him needing rewiring. Did that stop him? Again, the opposite is true.
“Frank Sinatra saved my life one night,” Mason recalled, albeit with a punchline. “He said, ‘Boys, that’s enough.'” While there was never any concrete evidence that he’d definitively ordered a hit on Mason and then had him beaten to a pulp, the comedian couldn’t overlook that he was the victim of mob-assisted violence twice after directing his wit towards one person in particular.
