By Elisa Jordan 

It’s almost impossible to pinpoint what makes someone iconic but some of our most memorable people seem to perfectly encapsulate a time or era and yet continue to remain timeless. Only a rare few reach such a status. At the top of that elite list sits Frank Sinatra, who remains Chairman of the Board after all these decades.

Francis Albert Sinatra was born on December 12, 1915, in Hoboken, New Jersey. He was the only child born to Italian immigrants Antonio, a former boxer and firefighter, and Dolly, a woman heavily involved in local politics. His parents doted on their son, but times weren’t always easy for the family.

BERGEN COUNTY, NJ – 1938: Pop singer Frank Sinatra poses for a mug shot after being arrested and charged with “carrying on with a married woman” in 1938 in Bergen County, New Jersey. (Photo by Michael Ochs Archives/Getty Images)

“Many think of Frank as a scrappy persistent fighter,” says Hollywood historian Amy Condit. “On the day he first entered the world when the 13 ½-pound baby was born not breathing. His grandmother held him under cold running water until he took his first breath. Frank’s daughter Nancy wrote a biography of her father, ‘Frank Sinatra: An American Legend,’ and she feels that Frank’s fight for life that day epitomized the struggle that would shape his ambition as an adult.”

As a child, Frank discovered he had a talent for singing and by the age of 8 was singing for tips. When he reached his teens, he was singing professionally with his parents supporting their talented offspring.

“It was a middleclass upbringing,” says Colman deKay, who worked directly with the Sinatra family to write a musical about Frank’s life for Radio City Music Hall. “He wanted to be a singer as a kid so his parents bought him a speaker and a microphone, sort of the rudimentary equipment. So bands would have to hire him because he was the only one who had the equipment.”

Their efforts paid off. Frank was eventually hired to sing in Harry James’ band and then later stolen away by Tommy Dorsey. It was during Dorsey’s stint at the Paramount Theater in New York that Frank Sinatra became a star.

“That’s where the Bobby Soxers discovered Frank and went crazy over him,” says deKay. “It was World War II so a lot of eligible men were away and he became this huge sex symbol. Hollywood was a natural next move after he walked away from his Dorsey contract and went solo after he became this huge sensation.”

11th December 1951: American popular singer and actor Frank Sinatra (1915 – 1998) with his wife, film actress Ava Gardner (1922 – 1990). (Photo by Walter Bellamy/Express/Getty Images)

Wheel of Fortune

Frank’s career soared for a few years but a number of factors began taking a toll on his success. After World War II the Bobby Soxers had grown up and were tending to their men who were now home from the war. He was also miscast in a couple of movies, which went on to receive disastrous reviews. What’s worse, Frank Sinatra, a married man with three small children, embarked on a turbulent affair with actress Ava Gardner, then considered one of the most beautiful women in the world. The relationship led to Frank divorcing his first wife, Nancy, and eventually marrying Ava, but unfortunately for the lovers their marriage was as tempestuous as it was passionate. Frank’s hard-won career appeared to be dead in the water and his finances began to suffer.

But those who counted Frank Sinatra out didn’t know who they were dealing with. He always remained that scrappy fighter from Hoboken.

“Frank rebuilt his career beginning with a series of concerts in Hawaii in April 1952,” Condit says. “While the crowds were small in size, they offered a large quantity of support to him. By responding to the audience’s warmth, he felt he delivered one of the greatest performances of his life. It marked a turning point in his career and personal life.”

A few months later, his then-wife Ava Gardner began campaigning on Frank’s behalf to have him cast as Maggio in the film adaption of “From Here to Eternity.” Her efforts paid off and not only was Frank awarded the role, he was rewarded for his performance with the Academy Award for Best Supporting Actor. Frank was back. Not only was he back, he was about to hit his stride.

From Star to Legend 

During the 1950s, Frank made a series of moves that vastly improved his career. In addition to his role in “From Here to Eternity,” he left his record company, Columbia, for a new contract at Capitol Records, a move that gave him more control over his music and access to better material. “The records he made in the ’50s with Capitol are just classic,” deKay says.

His career wasn’t the only thing changing. American culture was also evolving. The 1950s ushered in what is now called the cocktail culture, which became a sensation during the era.

Although the cocktail culture went mainstream in the 1950s, its roots actually took shape much earlier. If one wants to go back far enough, the authentic pirates of the Caribbean started mixing rums and it’s that idea—the mixing of drinks—that first constituted the idea of cocktails, says Hollywood and cultural historian Marc Wanamaker, who has authored many books on Hollywood history.

Fast-forward a couple of centuries to 1930s Hollywood. Inspired by Hawaii’s practice of mixing fruit drink concoctions, restaurants like Don the Beachcomber and the Cock’n Bull, and a little later the Luau, began experimenting with mixing fruity type drinks, which evolved to include liquor after Prohibition ended, making true alcoholic cocktails. At the time, what was called the “tiki culture” was finding an audience among Hollywood’s elite.

When World War II hit and the burgeoning cocktail scene was largely put on hold while men fought overseas and families rationed supplies back home. It wasn’t until America’s boys began streaming home, starting families and moving to suburbs that it roared back. The United States had won the war, Prohibition had ended and the Depression was finally over. Everyone, it seemed, was in the mood to celebrate.

circa 1955: Members of the Rat Pack (L-R): British actor Peter Lawford (1923 – 1984), American actor, singer, and dancer Sammy Davis Jr. (1925 – 1990), actor and singer Frank Sinatra (1915 – 1998), actor Joey Bishop, and actor and singer Dean Martin (1917 – 1995). All are wearing dark suits, and all but Bishop are holding drinks. (Photo by Jack Albin/Hulton Archive/Getty Images)

“During the war it was a whole different thing,” Wanamaker says. “There was no culture yet. It was really about 1949 when things changed with the nightclubs, bars, hotels and everything else into a 1950s, as they called it, a ‘cocktail culture.’”

It was in the 1950s that cocktail culture and tiki culture took off and hit the mainstream.

As families began their moves out to the new neighborhoods that were mushrooming up at a rapid pace across the nation, folks began throwing bar-be-ques and having get-togethers. Often, men would drink beer but as the 1950s progressed things became more refined. Everything became more elegant and feminine, meaning instead of cigars, hard booze and bars, it was all about cigarettes, cocktails and lounges, Wanamaker says. Whether people gathered in their friends’ homes or in nightclubs, they dressed appropriately in cocktail attire—this is where the term “cocktail dress” comes from—and when out were waited on by “cocktail waitresses,” women whose job was to bring mixed drinks to patrons.

And, Wanamaker says, “Frank Sinatra was involved in all of this big time.”

From his earliest days singing, Frank was part of the nightclub scene and watched it evolve during the course of his career. As he rebounded in the 1950s with better movie roles and recording material, he was poised to be the voice of the cocktail generation.

“Frank literally grew up in this culture,” Wanamaker says.

Dressed in a tuxedo while on stage and singing songs in the crooner style, he epitomized the smooth, elegant style of the cocktail era. “Dignity and glamour” is how Wanamaker describes the songs of Frank Sinatra from this era, along with the style of his pals in the Rat Pack, who began performing in Las Vegas to sold-out crowds. On stage, the guys—wearing their tuxes—would drink, smoke and croon to audiences.

“From the east coast, to the west coast to Vegas and his singing are these songs about love and songs about life and he puts everything in them, he is crooning them,” Wanamaker says.

Frank himself was well known for loving Jack Daniels and smoking cigarettes regularly. But there was a secret—Frank actually drank very little and, when smoking, didn’t inhale, deKay says.

When at a party or event, someone would fix Frank a drink—often Jack Daniels—with exactly four ice cubes. He would sip on it, and eventually someone would hand him a fresh drink. The illusion was that he was drinking heavily and often. The reality was he was just sipping at his drinks and it looked like he was tearing through multiple drinks when they were just continually being replaced. “He would get mad at bar tenders if they poured him too heavy a drink, if it wasn’t watered down enough,” deKay says. “He would say, ‘Do you think I could play in nightclubs all night and shoot movies all day if I’m drunk?’ No, he pretended to be drunk.”

Similarly, he was seen smoking but wasn’t a great lover of cigarettes. “It was the image,” deKay says. When out and about or on stage, he was seen smoking but didn’t inhale. He was concerned with protecting his voice and would even stop smoking all together in the weeks leading up to a recording sessions. “He’d get pissed at Sammy Davis for smoking too much and for real,” deKay says.

Frank’s instincts proved correct. His voice, which he so carefully looked after, lasted decades and he was able to continue performing.

The recordings he made, especially during his prime in the 1950s, stand the test of time. But it wasn’t just his music and drinking image that he put great care into. Frank Sinatra was equally particular about his clothing—crisp suits and hats tilted at just the right angle were also important to him. Taking all the parts of his image into account—the music, movies, clothing, and drinking and smoking—Frank epitomizes the core of the 1950s cocktail culture, elegance and glamour. Following Frank’s lead, all this has since become a classic style.

In fact, it made a big comeback at one point, although it never goes away altogether. “Retro 1950s/1960s cocktail culture had a comeback in the mid-1990s when swing dancing at night clubs became popular as evinced by the Jon Favreau film ‘Swingers,’ and the Ultra-Lounge compilation CD series made the Billboard Jazz top 10 in 1996,” Condit says. “It seemed that the mid-1990s also revived the Tiki culture and a rise in popularity for traditional tiki cocktails.”

The style is as timeless and classic and Frank Sinatra himself. His work will last forever. So will the image.

He seemed to know this, or at the very least hope for it.

“He always used to end his shows with ‘May you live 100 years may the last voice you hear be mine,’” deKay says. “Then as he got close to 100 years old he would say ‘150!’ or ‘175!’”

THE TONIGHT SHOW STARRING JOHNNY CARSON — Pictured: (l-r) Actor/comedian George Burns, guest host Frank Sinatra on November 14, 1977 — (Photo by: Gary Null/NBC/NBCU Photo Bank via Getty Images)