A History of Frank Sinatra's Most Gangsta Moments

Image via Complex Original

From blue-haired old white ladies to the illest hip-hop kid on the block, everybody loves Frank Sinatra. Rappers like Jay-Z have boasted about being “the new Sinatra” while Diddy thinks of himself as “the Black Sinatra,” but neither boss has the kind of swag to rival the original Chairman of the Board.

Maybe that’s why over a decade after his death we’re still celebrating Ol’ Blue Eyes. This week a new Sinatra compilation album hit stores, Sinatra: Best of the Best. With his songs still a huge part of American culture, we figured it was the perfect time to take a walk through the Rat Pack glory days and discover the moments that made Frank a true O.G.

Written by Michael A. Gonzales (@gonzomike)

Rough Childhood

Talking to journalist David Lewin in 1964, Sinatra told the writer about the rough hood where he raised in Hoboken, New Jersey. “Even as a youngster, I thought about what I was going to do when I grew-up,” he said. “Many of my childhood friends grew-up to serve sentences of from 10 to 15 years in jail. If I hadn’t broken away, I might have ended up like them too. I got interested in music at 13—perhaps it soothed the savage beast.”

Getting Out of His Contract

In the beginning of his career, when Sinatra was just a skinny kid crooner from New Jersey, he signed a crazy contract with bandleader Tommy Dorsey for the right to be in the famous trombonist's group.

Dorsey demanded that the young singer pay him one-third of his earnings for life and an additional 10 percent to his agent. According to journalist Anthony Bruno, “By the terms of the contract, 43% of Frank Sinatra would belong to Tommy Dorsey and his agent forever.”

In his article “Frank Sinatra and the Mob,” Bruno writes, “In 1943, Sinatra's representatives tried to get him out of the contract, offering Dorsey $60,000 to rip it up. Dorsey, who had a reputation for being tough, refused."

Bruno continued, writing, "By some accounts, hard negotiation eventually convinced the bandleader to take the offer, but other accounts say that Sinatra's godfather, Willie Moretti, convinced Dorsey to see the light…Moretti bragged in private that he and a few associates paid an unannounced visit to Dorsey in Los Angeles. Moretti allegedly jammed the barrel of a gun into the trombonist's mouth and got him to release Sinatra from his obligations in exchange for one dollar."

Beefing With Mario Puzo

In a 1972 New York magazine article recounting the success of The Godfather, author Mario Puzo wrote that Sinatra hated him, because he believed the lounge singer character Johnny Fontane in the best-selling book was based on him.

Later, after a mutual friend introduced the two men at the trendy restaurant Chersen’s in Los Angeles, Sinatra cursed out Puzo and called the writer a pimp.

“I do remember him saying that if it wasn’t that I was so much older than him, he would beat the hell out of me,” Puzo claimed. Deciding it was in his best interest to leave, a humiliated Puzo recalled Frank screaming after him, “Choke. Go ahead and choke.”

Divorce That Dame

In 1968, when his third wife Mia Farrow was filming the horror picture Rosemary’s Baby, the singer was set to begin playing a New York City cop in the movie The Detective. Since Farrow was supposed to be in his film as well, Sinatra placed a call to producer Robert Evans and demanded the actress be released from Rosemary’s Baby.

According to Evans’ memoir, “Frank didn’t bark; he bit.” However, when Farrow refused to leave the production, Sinatra had her served with divorce papers right on the set.

Dating Tips

In the late-‘50s, a young Atlantic City showgirl named Marilyn Miller caught the eye of Sinatra at the 500 Club. The following day he had his pals from the police department locate her and arrange a date.

According to Miller, “The reason the police came to get me was because this was 1959, and he was at the height of his popularity. The police had to drive into the kitchen (of the club), and Frank had to get in the car and be taken out—he couldn’t be out on the street.”

Crossing The Color Line

When Sinatra died in 1998, CNN's Steve Bartelstein reported on CNN Talkback Live a story of Frank dealing with racism at a ritzy New York City restaurant in the 1950s. "He took (singer/actress) Lena Horne to the Stork Club,” Bartelstein recalled. “The Stork Club at that time didn't allow Blacks. So the manager fumbled around, went back, looked in, you know, the reservation book, came back. Obviously, they weren't going to seat her. And they said to him, `Mr. Sinatra, who made your reservation? We don't seem to have it.' And Sinatra said, ‘(President Abraham) Lincoln.'"

Sammy Sees No Evil

Harlem born Sammy Davis Jr., perhaps the most talented of Sinatra’s celebrated clan the Rat Pack, lost his left eye in a car accident in 1954. When the F.B.I. questioned him about Sinatra’s supposed mob connections, Davis explained to the feds, “Baby, let me say this. I got one eye and that one sees a lot of things that my brain tells me I shouldn’t talk about. Because, my brain says that if I do, my one eye might not be seeing anything after a while.”

What You Think All The Guns Is For?

At his home in Rancho Mirage, California, Sinatra had a gold plaque attached to the entrance that read: Never Mind the Dog, Beware of the Owner.

Sinatra’s 11

After overhearing some random guys talking about the chances of getting away with robbing the Sands Casino in Las Vegas, actor Peter Lawford bought Sinatra the concept for the original Ocean’s 11. Supposedly, after listening to the idea, Frank joked, “Let’s not make the picture, let’s pull the job.”

Drink Up

Singing on stage in an Atlantic City Hotel in 1983, Sinatra began talking about his childhood growing-up in Hoboken. “Believe it or not, I used to drink malts (milkshakes) then,” he said. “Can you believe that? That was before I learned about Jack Daniels.” After taking a swig of the strong brown liquor, he smiled. “Boy is that better.”

Goons R Us

In 1974, Sinatra was sitting in a New York City bar with journalist/novelist Pete Hamill and a crew of young goons that the writer later described as, “the junior varsity of the mob.” They were all watching a Jets game and when the commercial came on, Frank looked at the young gangsters and said, “Jesus, there’s about forty-three indictments right at the bar.” His friend Pat Henry looked at Sinatra and added, “Present company excluded.” They all laughed.

First Lady Blues

While Sinatra was friends with future president John F. Kennedy, putting much effort into getting him elected, the future first lady wasn’t a Frank fan. Believing that the singer was a bad influence on Kennedy, she snubbed Sinatra whenever possible.

Sinatra thought she was simply prejudiced “against wops” and, according to former valet George Jacobs in his memoir Mr. S., whenever Jacqueline Kennedy appeared on television, Sinatra screamed angrily, “I’d like to fuck that bitch.” As an aside, Jacobs noted, “He’d have never said that about any women he liked.”

Clothes Make The Man

In 1961, after helping Kennedy get elected president, Sinatra was invited to the inaugural party in Washington, D.C. Yet, after arriving in the capitol, he soon realized that he had personally packed the wrong pants for his custom tailored suit. Although there was a massive snowstorm in D.C. that day, Sinatra instructed valet George Jacobs to fly back to Los Angeles and retrieve the correct pants.

First Round KO

In 1947, Sinatra was arrested the day after getting into a fight with Hearst newspaper columnist Lee Mortimer, who had been writing negative items about the singer being involved with both the Mob and the Communist Party.

One night outside of Ciro’s in Los Angeles, he punched the writer in the face. “It was all over in about 15 seconds,” Sinatra said later. “I hit him right on the jaw. It’s the only place I know to hit a man and knock him down.” Later, Time magazine wrote that the Hearst papers gave the story “headlines and space almost fit for an attempted political assassination.”

Dead That DJ

New York City disc jockey Jonathan Schwartz has spent most of his career celebrating the music and legacy of Frank Sinatra, yet he felt the singer’s wrath in 1980 when he dared to criticize the third disc of Trilogy: Past, Present and Future.

While the three-record album contained Sinatra’s soon to be classic “Theme from New York, New York” on the “present” disc, it was the “future” disc that Schwartz referred to on WNEW-FM as “narcissistic” and “a shocking embarrassment.” After Sinatra called Schwartz and cursed him out, he then got the program director to fire him. Luckily, he was hired back three months later.

Sammy Gets The Cold Shoulder

Although Sinatra and Sammy Davis Jr. were friends for years, the blue-eyed singer felt disrespected when Davis told a Chicago radio station in 1959, “I love Frank and he was the kindest man in he world to me when I lost my eye and wanted to kill myself. But there are many things that he does that there are no excuses for. Talent is not an excuse for bad manners. I don't care if you are the most talented person in the world. It does not give you the right to step on people and treat them rotten. That is what Frank does, occasionally.”

That same year, Sammy Davis Jr. was supposed to co-star with Sinatra in Never So Few, but was replaced by Steve McQueen. Fan site Franksville says, “Sinatra cut him (Davis) off for several months after hearing about these statements, without ever talking to him about them. Davis, of course, was devastated—as Sinatra knew he would be.”

Kitty’s Nine Lives

When writer Kitty Kelley got a deal in 1981 to write an unauthorized biography of Frank Sinatra called His Way, the singer sued her for two million dollars before a word was typed.

Years later, actor Tony Danza told her she was lucky to be alive. However, Kelley wrote in 2010 that Sinatra told a friend, “I hope nothing happens to that goddamned broad, because if it does, I’ll be the first one blamed.”

Riddle Me This

One of Sinatra’s longest creative relationships was with conductor and arranger Nelson Riddle. A mild-mannered man who drank too much, Riddle once described his former boss as, “…a perfectionist who drove himself and everybody around him relentlessly. You always approached him with a feeling of uneasiness, not only because he was demanding and unpredictable but because his reactions were so violent.”

Buddies With Bono

In 1993, when producer Phil Ramone was putting together Sinatra’s wonderful Duets, which featured contributions from Luther Vandross (“The Lady is a Tramp”) and Gloria Estefan (“Come Rain or Come Shine”), it was decided to match Ol’ Blue Eyes with U2 lead singer Bono.

“I don’t usually hang out with men who wear earrings,” Sinatra told the singer. Later, when the two became buddies, Bono admired one of Frank’s own paintings hanging on the wall of his Palm Springs home. Sinatra removed the painting and gave it to Bono as a gift.

Bogie And Bacall

In 1956, Sinatra became friends with tough guy actor Humphrey Bogart. Shortly after they became close, Bogart was diagnosed as having throat cancer and Sinatra visited him often and, in the process, got to know Bogart's wife Lauren Bacall well.

A year later, on January 14, 1957 Bogart died. Afterwards, Sinatra was often in the company of Bogie’s widow. The following year, Sinatra proposed to Bacall, who agreed to marry him. Nevertheless, Frank left the following morning for Miami.

That evening Bacall was questioned by a journalist who reported the news to the world. When Sinatra saw the papers, he admonished Bacall and she didn’t hear from Frank again for years. According to Sinatra’s second wife Ava Gardner, he claimed that he never had any intention of marrying ‘that pushy female.’”

All Or Nothing At All

Considered by many to be one of the greatest magazine pieces ever published, Gay Talese’s 1966 Esquire magazine story “Frank Sinatra Has a Cold” is still widely read amongst Ol’ Blue Eyes aficionados. Although he never got a chance to interview the singer, he did hangout with him and his crew. "I'd kill for him,” Sinatra’s friend Brad Dexter told the writer.

Talese later wrote, "While this statement may seem outlandishly dramatic…it nonetheless expresses a fierce fidelity that is quite common within Sinatra's special circle. It is a characteristic that Sinatra, without admission, seems to prefer: All the Way; All or Nothing at All. This is the Sicilian in Sinatra; he permits his friends, if they wish to remain that, none of the easy Anglo-Saxon outs. But if they remain loyal, then there is nothing Sinatra will not do in turn -- fabulous gifts, personal kindnesses, encouragement when they're down, adulation when they're up. They are wise to remember, however, one thing. He is Sinatra. The boss. Il Padrone.”

Between Me And God

While some bad boys often praise God or contribute to their local church in hopes that their earthly sins are forgiven, Sinatra was a much more complex man when it came to religion.

In a 1963 interview with Playboy, he said, “I don't believe in a personal God to whom I look for comfort or for a natural on the next roll of the dice. I'm not unmindful of man's seeming need for faith; I'm for anything that gets you through the night, be it prayer, tranquilizers or a bottle of Jack Daniel's. But to me religion is a deeply personal thing in which man and God go it alone together, without the witch doctor in the middle.”

Love And Marriage

Although he was without a doubt a womanizer, Sinatra was married four times. Yet, it was his second marriage to movie star bombshell Ava Gardner that his friends and biographers agree was the love of his life. Already married to his first wife Nancy for 11 years when he met Ava, they soon split and he married Gardner 72-hours after the divorce was final.

However, Ava and Frank fought constantly and often made the national headlines with their violent behavior, broken furniture and gunplay. "He has a temper that bursts into flames, while my temper burns inside for hours," Gardner said.

According to People magazine, after the couple divorced six years later, Sinatra “…suffering from insomnia and depression, drowned himself in liquor and remorse. At his L.A. apartment one night, he walked away from a card game with songwriter Sammy Cahn and others and went into his den, where he tore up a photograph of Gardner and smashed the frame. Then he began trying to put the photo back together. For many years, on sound stages and in dressing rooms, Sinatra kept a picture of Ava taped to his mirror.”

The Blue-Eyed MF

Producer Quincy Jones had been friends with Sinatra for years. There was no gray in him, you know?” Q told Bonz Malone in a VIBE profile of Sinatra. “He loved you or he was ready to kill you.”

Q and Count Basie collaborated with Sinatra on his swinging 1964 single “The Best is Yet to Come,” which was also the last song he ever sang in public. They also recorded the definitive version of “Fly Me To The Moon,” which became the first song ever played there.

“Frank’s one of the best ever,” Q told Malone, “in terms of pitch and identification and style and phrasing. Lyrically he was like an actor. He could take a lyric and make you believe anything. When we did 'Fly Me To The Moon' that song was originally called 'In Other Words.' A lot of other people had recorded it, but when Frank finished with it, the most repeatable line was "Fly me to the moon." Later I met Buzz Aldrin, you know, the dude who walked on the moon. He said, "When we landed on the moon, I reached back in the cabin and pit on the cassette with you and Basie and Frank."

According to his 2001 autobiography, Quincy spent a lot of time with Sinatra in his last days, “…sitting by his bed as Alzheimer’s took its toll. One day he impatiently demanded coffee with cream and sugar. When the nurse came in with the coffee on a tray, he took one look at it and said, ‘What are you bringing me that for? You know coffee makes me nervous.’ She backed out of the room.

After she left, he looked at me and said softly, ‘Q, I’m a pain in the ass, right?’ I laughed and said, ‘Right. Yes—you are. You always have been, but I still love you, you blue-eyed muthafucka.’”

You Only Live Once

Always a quotable kind of guy, when Sinatra turned fifty, he said, “You only live once, and the way I live, once is enough.” Thirty-two years later, Frank Sinatra died on May 14, 1998 at the age of 82. The words “The Best Is Yet to Come” are engraved on his gravestone. He is buried inside Desert Memorial Park in Cathedral City, California.