A book has recently taken my life over, Sinatra: The Chairman by James Kaplan. In case you didn’t see me mention it first in a “But Have You Heard” article for Grumpire, The Chairman covers Frank Sinatra’s career from the moment he experienced an unpredictable resurrection following a rough lull. He won Best Supporting Actor at the 1954 Academy Awards for his performance in From Here to Eternity, and that victory is credited to beginning Sinatra’s power as a middle-aged icon after his time as a youthful heartthrob had come and gone.

I’m a fiend for old Hollywood gossip, and the 992 pages that make up The Chairman are filled with it. Hollywood gossip rarely contends with Sinatra tales for a variety of reasons. Similar to The Beatles and Elvis, Frank Sinatra’s career reached a monumental peak few reach. He also had a relationship with the mafia back when mob enforcers would go anywhere with a jukebox and dictate what would be played.

He had everything going for him and on top of that, nobody embraced excess like Sinatra. He regularly stayed up drinking well into the morning in Las Vegas when it was still Sin City. After hearing of those long drinking hours and the power he wielded, it won’t be surprising to hear Sinatra could get sadistic. Standing at 5’8”, he was a textbook case of the Napoleon Complex. I’ll get to an example with a unique story that could only exist in the life of Frank Sinatra.

One of the mobsters Sinatra could call on was Sam Giancana. Somewhere around the spring of 1961, Giancana voiced his intense hatred for The Untouchables. Not only did the show attract protests from The Federation of Italian-American Democratic Organizations, but it hit too close to home for Giancana. Not only was he a mobster, but it’s reported he started his criminal career as a driver for Al Capone, the show’s main villain. The Untouchables was produced by Desilu Productions, so Giancana found a target in Desi Arnaz.

Frank Sinatra had never seen an episode of The Untouchables, but he wanted to fight for his people and the mobsters who supported his career. While on a rare break, Frank was in Palm Springs and went to the Indian Wells Country Club, a restaurant that Desi Arnaz was known to attend. Prior to this, Sinatra and Arnaz had a mutual respect for one another, not like it mattered. One thing you learn about Frank Sinatra is nobody was more eager to burn a bridge than him.

Desi that night was accompanied by two bodyguards. Because of their presence, Arnaz wasn’t intimidated by Sinatra. Even without their presence Desi Arnaz would’ve probably still stood his ground. This next detour puts a spotlight on Desi’s bold confidence. If you enjoy Hollywood gossip, it’s worth your time.

This Desi Arnaz story comes from a podcast infamous for collecting old Hollywood gossip, Gilbert Gottfried’s Amazing Colossal Podcast. It was told on episode 229 by writer Ron Friedman, a man with a memorable career. He was a writing partner for five years with Johnny Carson’s head writer Pat McCormick. Friedman also created the character Uncle Arthur for Bewitched, which got Paul Lynde on the show. It should be mentioned Paul Lynde has a reputation for being a drunken anti-Semitic. Friedman confirmed the rumor by saying, “When he had too much to drink he was Rudolf Hess.”

While working with Lucille Ball, Ron Friedman asked her about signing Orson Welles to Desilu Productions for a brief period. Friedman says that Lucy and Desi approached Orson during an odd time. He was living at the Chateau Marmont, he owed $100,000 to a nearby liquor store, and was charging sex workers on a credit card. The arrangement was they would cover Orson’s debt and he would live in their Palm Springs home while writing something for them.

Seven to eight weeks went by and Orson Welles hadn’t written anything. To make it worse, he was buying a morbid amount of food, alcohol, and tailored suits on Lucy and Desi’s charge account. The day finally came when Desi asked what the tab was up to. When Lucy told him, Desi cried out “That’s it!” He pulled a gun out, stating “I’m gonna talk to him.” Desi had been drinking, and Lucy said, “You’re not gonna drive to Palm Springs now in the middle of the night with your gun while you’re half loaded.” Desi simply replied, “I’m gonna talk to Orson, and he’s gonna answer me correctly.”

The next morning Desi returned, and Lucy asked what happened. Desi said, “I put the gun in his nose and I said, ‘You fat fuck, you’re gonna bring us something we can shoot in three weeks or I will kill you.’” Ten days later Orson turned in a script for The Fountain of Youth, a Peabody Award winning short that aired on Colgate Theatre.

Now you might understand how Desi Arnaz still would’ve stood his ground without the bodyguards.

With the bodyguards there, there was zero chance for Arnaz to be intimidated by Sinatra informing him that his “influential Italian friends” didn’t care for the show. Sinatra had no muscle on his side, only composer Jimmy Van Heusen, and the dates accompanying them. It’s said Desi called Frank Sinatra a failure in the television industry. The woman Van Heusen was with that night reported Arnaz said, “I remember when you couldn’t get a job. So why don’t you forget all this bullshit and just have your drinks and enjoy yourself. Stop getting your nose in where it doesn’t belong, you and your so-called friends.”

Eventually the two men separated, and Sinatra told Van Heusen and the women accompanying them, “I just couldn’t hit him. We’ve been pals for too long.”

Here’s where Frank Sinatra’s dark side comes alive.

Later on that night, Sinatra and his group went over to Van Heusen’s Palm Desert house for a party around 4am. During a booze-soaked temper tantrum, Sinatra stormed into Van Heusen’s den. There was a self-portrait of Jimmy Van Heusen sitting at the piano in his pajama top painted by Norman Rockwell. Sinatra grabbed a carving knife and destroyed it. He then looked over to at Van Heusen and said, “If you try to fix that or put it back, I will come and blow the fucking wall off.”

One of the women, in an attempt to lighten the mood, said, “I love your records Frank.” His reply? “Why don’t you go slash your wrists.”

It’s eerie that Sinatra was reported mentioning wrist-cutting because in the fall of 1953, he slashed his left wrist in Jimmy Van Heusen’s New York apartment. His marriage to Ava Gardner was concluding, and she was in Spain lusting over a bullfighter. Van Heusen came home just in time and rushed Frank to the hospital. The narrative of James Kaplan’s book points to an ingredient in this Sinatra temper tantrum (besides Desi Arnaz) being Jimmy Van Heusen seeing him during such a weak moment in his life and forever resenting him for it.

The stories found in The Chairman are great because it’s a miracle they ever got printed. Sinatra came from a pre-internet world where few knew your private life and secrets could be guarded. If a photographer got too close, Sinatra punched him. In his lifetime, the only rumors that saw print were whenever Louella Parsons or Dorothy Kilgallen reported on his love life.

If you need an example of what happened when people ran their mouth about Sinatra when he was alive, you only need to look at Jackie Mason. When Frank Sinatra was fifty and married to 21-year old Mia Farrow, Mason was on stage saying, “Frank soaks his dentures and Mia brushes her braces, then she takes off her roller skates and puts them next to his cane. He peels off his toupee, and she unbraids her hair.” Mason got threatening phone calls, but he hired a bodyguard and kept telling the jokes. The next incident Mason experienced was someone firing three shots through the glass patio door of his hotel room.

For awhile, this incident got it through to Jackie Mason that he should toss out any Frank Sinatra material. Eventually time passed and he wasn’t afraid anymore. At the Saxony Hotel in Miami he said, “I have no idea who it was who tried to shoot me. After the shots were fired, all I heard was someone singing ‘doobie, doobie, doo.’” The threatening phone calls started again, people in the lobby confronted him, and one night while in a car with a woman, the door on Mason’s side opened and he was punched hard enough to get multiple face lacerations and a broken nose. The person who did it said, “This is not the worst that can happen if you don’t keep your mouth shut about Frank Sinatra.”

My obsession for this book is so severe that this isn’t the first time I attempted writing a Frank Sinatra-themed piece. In February I attempted writing a double feature article that would put a spotlight on two films where Frank Sinatra embraced some darker roles, Suddenly and The Man with the Golden Arm.

When I read about Suddenly, I immediately ordered the Blu-ray. It’s the one time in Frank Sinatra’s filmography where he played a villain, someone attempting to assassinate the president. Sinatra is incredible, the only problem is everything around him is painfully hokey. Remember those “golly gee willickers” ’50s tropes that Pleasantville parodied? Triple it.

Outside of Sinatra’s performance, the one other memorable feature in Suddenly is seeing Paul Frees, an iconic voice actor, in a rare on-screen role. For all you Rankin/Bass fans, you might take pleasure in seeing the voice of Burgermeister Meisterburger playing a mobster killing cops before dying in a shootout.

The Man with the Golden Arm is also something I unfortunately couldn’t recommend. It was directed by Otto Preminger, and was one of the few occasions Frank Sinatra was willing to collaborate with a director. Throughout his film career, Sinatra earned the nickname “One Take Charlie” because he was only willing to do one take. Sometimes it was because he grew impatient and wanted a film to be over as soon as possible, other times it was because he believed that the first take was the one time he’d be able to show real emotion. Along with being One Take Charlie, Sinatra was known for leaving a set if the director didn’t agree with him on every single detail.

All of that was abandoned for The Man with the Golden Arm. Sinatra was willing to do more than one take, and even went to bed at a reasonable hour. The reason for this change was Sinatra fully believed his performance as Frankie Machine would win an Academy Award for Best Actor.

Sinatra was nominated, but didn’t win. Ernest Borgnine won for Marty. Peggy Connelly, Sinatra’s date that night, is quoted in Sinatra: The Chairman sharing Sinatra’s response to the loss:

“I had wanted to go to the parties they held afterwards, but we walked out, got in the car and went home. He went into his bedroom, didn’t turn the light on, just sat down on the bed. I finally decided to go in.

“I kneeled down on the floor and put my arms around him. It’s embarrassing now to remember what I said to him: ‘It’s terrible. But Ernie Borgnine is fat and ugly, think what it’ll do for his career.’ Frank said, ‘Yeah, but think what it would’ve done for mine.’”

The Man with the Golden Arm doesn’t hit as hard now as it did in 1955. For a generation, the film was their first look at drug addiction. What was once a film that dragged viewers into unimaginable darkness now plays like a storyline on a network soap opera. Frankie Machine’s journey through the North Side of Chicago with a wife who became crippled from his drunken nights on the road is overly melodramatic compared to Requiem for a Dream and Trainspotting. Even with the faults, The Man with the Golden Arm is worth respecting for its ambitious look at drug addiction back when Reefer Madness hadn’t even celebrated its twentieth anniversary.

After that failed double feature, I continued reading Sinatra: The Chairman, and finally landed on a movie with a unique backstory, Tony Rome.

It begins with a script titled Harper, written by William Goldman based on the Ross Macdonald novel. Frank Sinatra was originally going to star in it until negotiations fell through. The film wound up casting Paul Newman and became a box office success.

Harper is a private investigator film that pays tribute to the iconic ground covered by Humphrey Bogart in The Maltese Falcon and The Big Sleep. It also co-stars Lauren Bacall, who was not only married to Humphrey Bogart before he passed from esophageal cancer, but was also once in a serious relationship with Frank Sinatra. From what’s reported, they had plans of being married. One story features them at a restaurant where Lauren Bacall was about to sign an autograph for a girl before Sinatra said “give her your real name.” She signed it “Betty Sinatra.”

Plans for marriage died after Bacall attended a play with her agent, Swifty Lazar. Louella Parsons was there, and asked Bacall if her rumored engagement to Sinatra was true. Bacall said, “Why don’t you ask him?” before walking to the bathroom. As she walked out she saw Parsons quickly rushing away. Later that evening she saw on the newsstands “SINATRA TO MARRY BACALL.” Swifty Lazar had told Parsons the rumors were true, and she rushed out with the story.

Sinatra’s response was feeling betrayed. Like most who unfortunately got close to Sinatra, he iced Lauren Bacall out. During the final times they spent together, he was unemotional and never reacted to her presence. He soon pursued other dates and, as he was known to do, eventually returned to Ava Gardner for a moment before their chaotic personalities collided and reminded the nostalgic lovers why they got divorced. 

Around the time Tony Rome came into his life, Sinatra’s film career was in a transition. For a few years he made a series of Rat Pack films beginning with Ocean’s 11. Whether it’s that film or Robin and The Seven Hoods, most agree any behind the scenes antics had to be more entertaining than anything captured on film.

Two years before Tony Rome, Sinatra and Dean Martin made Marriage on the Rocks. It’d be the last time to two men were on screen together until a brief cameo in Cannonball Run II.

The Rat Pack gimmick was coming to an end, and earlier in 1967, Sinatra ended his ties with Warner Bros following The Naked Runner, a film that left nobody asking for more. There was a lot of uncertainty as Sinatra felt the generation gap breathing down his neck. Occasionally he had victories like “Strangers in the Night” knocking The Beatles’ “Paperback Writer” out of the #1 spot on the Billboard Top 100, but Sinatra was rarely satisfied. His longtime valet George Jacobs claims there was a day when Sinatra heard The Doors’ “Light My Fire” on three different radio stations, and responded by destroying the car radio with angry kicks.

The lost opportunity of Harper and the offer for Tony Rome got Sinatra thinking that a great way to revitalize his career would be to do the hardboiled detective films that made his friend Humphrey Bogart an immortal screen icon. Humphrey Bogart was not only a friend, but a member of The Rat Pack when the group was just a collection of famous drunken pals and not a Vegas lounge act. The nickname was created by Lauren Bacall when she referred to Sinatra, Bogart, and Judy Garland as a “rat pack.”

The stories revolving around two of the performers in Tony Rome made me want to see this movie and use it as the Trojan horse for everything seen here. First there’s Tiffany Bolling, an attractive actress you briefly see in Tony Rome as a woman in a Playboy bunny outfit taking Polaroids. While married to Mia Farrow, Sinatra fooled around with Bolling, who, at the time, was a year younger than Farrow. On second thought, maybe Sinatra wasn’t sweating the generation gap.

Sinatra once introduced Mia Farrow at The Sands Hotel and Casino and told the crowd, “Yeah, sure I got married. Well you see, I had to. I finally found a broad I can cheat on.” He wasn’t lying.

Here’s what Bolling says of the fling:

“I really did love that man. He was a king of men, and he treated me like a princess and a queen all the time. Never, ever was there any kind of abuse or any kind of weird stuff–except one time, he hired some hooker, and he wanted me to participate, and I said, ‘Eff you, man I’m leaving.’ And I did.”

Someone also starring in Tony Rome with an interesting story is comedian Shecky Greene. The two became friends after Greene opened for Sinatra. Sinatra admired the way the comedian, similar to Desi Arnaz, refused to be intimidated by Sinatra. Greene has said he once met Sinatra’s mother and she said, referring to his inability to be afraid, “He likes you because you’re me.”

Frank Sinatra’s friendship with Shecky Greene was short-lived. Sinatra’s drunken mood swings were too much for Shecky, and he had no problem saying so. Sinatra once said “Shecky, stick with me and I’ll make you the biggest star in the business.” Greene’s reply was, “If being a big star means being like you, then I don’t want it.”

Later that evening, Shecky was attacked by three of Sinatra’s bodyguards in the hotel lobby. He got a concussion and a gash on his temple. Sinatra quickly felt remorseful because Shecky had a fan in Sam Giancana. If you’re somehow following this, you might be wondering why Sam Giancana would take the word of Shecky Greene over Frank Sinatra when the two were once closely associated.

In the years since the altercation with Desi Arnaz, Sinatra had angered Sam Giancana. When Frank’s kid, Frank Sinatra Jr. was kidnapped, Sinatra declined help from Giancana twice. Since it was a high profile case, Sinatra was terrified of his mob connections becoming more than a whisper and was adamant that Giancana let the FBI take control of the situation. Giancana didn’t agree, and like everybody Sinatra interacts with, the two drifted apart.

When Giancana asked Greene what happened after Sinatra begged him to not rat him out, Greene only said, “Nothing, I fell down the stairs.” The incident eventually led to one of Greene’s more memorable jokes, “Sinatra saved my life in 1967. Five guys were beating me up and I heard Frank say, ‘That’s enough.’”

This all happened in the middle of production for Tony Rome, and Sinatra had the large gash on Shecky Greene’s forehead written into the film. His character is depicted as getting a severe head injury from a car crash and later on it looks like Rocky Graziano, who’s also featured in Tony Rome, put him down for a ten count.

Speaking of Tony Rome, I think I’m ready to talk about this movie.

The theme is performed by Frank Sinatra’s daughter, Nancy. Around the same time, Nancy was experiencing the peak of her career. After a publicity makeover where she was turned into an era-defining sex symbol, she released the single “These Boots Are Made for Walkin’.” Nancy says during the recording sessions that producer Lee Hazlewood told her to sing it “like a 14-year old girl in love with a 40-year old man.” After a first take that didn’t work, Hazlewood revised his instruction, now telling her to sing it like “a 16-year old girl who fucks truck drivers.” It apparently worked because that’s the version we’ve all heard.

The Tony Rome theme is a fun, energetic track that’s also kind of creepy. Nancy sings about how her dad will be getting any daughters roaming the streets in the first verse. The next two lines that follow are “pussycats out run astray, he will bring them back today.” This isn’t the only questionable collaboration between Frank and Nancy. There’s also their cover of “Something Stupid” which some refer to as “The Incest Song.”

Most would probably consider Tony Rome an outdated guy’s movie. The film begins with the camera zooming in on a bikini-clad babe’s butt before quickly cutting to a boxing gym. That isn’t the only zoom-in on a girl’s butt you see in Tony Rome, it also happens at the end. Outside of porn, it might be the only film bookended with butts.

Some of the film’s memorable dialogue certainly won’t win over stale audiences today. One that comes to mind is a character saying, “Somebody’ll squeeze something out of Tony the day Georgia elects a colored governor.”

Any woke summaries really go out of their way to ignore the fun simplicity of this neo-noir. Tony Rome’s energizing crime storyline is comparable to anything written by Elmore Leonard. It successfully carries on the tradition of detective stories that saw memorable peaks like Billy Wilder finding shadow-shrouded corners in a city as sunny and bright as Los Angeles when he adapted James M. Cain’s Double Indemnity, a film whose script was co-written by noir icon Raymond Chandler.

The plot of Tony Rome is similar to most private investigator stories. Tony Rome takes on the simple task of taking a wealthy girl home, played by Lolita’s Sue Lyon. Next thing he knows, two goons are ripping his boat home apart looking for a pin, a pin that the socialite later requests him to find because it’s worth $5,000.

Tony Rome contains the thrilling excitement you tend to find in next generation private investigator stories. Along with violent murders, you also have drug dealers and lesbian strippers. Tony Rome gives its audience a thrilling amount of excess.

Along with the action, I mentioned earlier this film has memorable dialogue. Jill St. John stars in Tony Rome a few years prior to becoming a Bond Girl in Diamonds Are Forever. She and Sinatra have some great interactions. At one point she says, “Every man you meet thinks you wanna play slap and tickle,” to which he replies, “Tell them you’re not interested.” She then says with a smile, “Well that’s the trouble, sometimes I am.”

In another scene, Tony Rome is walking out of a house late at night just as a man is walking in. Rome says, “You always come in this late? No wonder your wife’s in heat.” The film effectively captures the type of dialogue essential to these films, the type of lines Mickey Spillane injected into his Mike Hammer novels.

One of the most ridiculous additions I’ve seen in a movie features Tony Rome snoozing in his office when a client comes in talking about her cat. The word “pussycat” is used, and eventually it’s shortened to where the woman says, “My pussy used to be so sunny and full of fun with the sweetest smile,” to which Rome replies, “You got a pussy that smiles?” I imagine in a straight to DVD National Lampoon film I’d groan in agony from that exchange, but for whatever reason, watching this take place in a 1960s Sinatra detective film excited me like the rest of this film’s flashy, hard boiled exploitation.

Tony Rome works because it’s a fun action film only here to please and excite. It works because this is the closest and most effective Sinatra came to playing a version of himself. Similar to Tony Rome, Sinatra could also be found tossing back drinks in the more alarming corners of society.

I’m fortunate to find a film that gives me so much of what I want. At the same time, I’m sad a film from 1967 is this exciting. Shouldn’t movies have evolved to a place where anything from 1967 is like trying to watch The Man with the Golden Arm post-Trainspotting? Unfortunately it’s rare to find a film aimed at adults that is allowed to offer this much stimulation. Occasionally you get something like The Nice Guys, but it’s a rarity.

It’s time for this piece to finally sing “My Way.” Throughout this you’ve been fed an alarming amount of antique Hollywood gossip, and there might’ve even been a film recommendation somewhere. There was certainly time devoted to a book recommendation. When’s the last time anybody read? Probably back when Rex Reed did an interview for Esquire where he asked Ava Gardener about Mia Farrow and she replied, “Ha! I always knew Frank would end up in bed with a boy.”


  • Emilio Amaro

    Outside of writing about movies, Emilio’s interests include watching Gilmore Girls, sharing gossip about Paul Lynde and admiring the work of beloved character actor Phil Fondacaro. Amaro Emilio
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