The Wager, Volume 8(8) – Sinatra: Sinner or Saint?

This week The WAGER announces the release of the fourth volume of the Harvard Medical School Division on Addictions web initiative, Addictions & the Humanities. The aim of this initiative is to create a public forum to discuss literature, art, music, and performing arts related to addictions, including pathological gambling. Science and technology will always help us understand addiction, but truth also may be revealed by examining art.

Below is a segment of an article from the fourth issue of Addictions & The Humanities that examines Frank Sinatra’s association with alcohol in his performances and private life.

Frank Sinatra: The Icon, The Voice, The Chairman of the Board, Ol’ Blue Eyes. Celebrated member of The Rat Pack. When we think about Frank, we conjure images of vintage Las Vegas, of big entertainment, fast lives, and excessive behavior. His public performances were frequently associated with risky behavior, particularly with drinking alcohol. But were Frank Sinatra and the other members of the rat pack heavy drinkers, or was it all part of their performance? Were they taking risks, or creating a seemingly risky persona to help their careers and generate a daring and edgy image? This article briefly discusses the life of Frank Sinatra and attempts to analyze his public and private relationship with alcohol.

People who grew up listening to music in the 50s and 60s will inevitably own a few Sinatra albums among their prized musical possessions. Perhaps it was your parents (or you) who hummed to “My Way” for inspiration in trying times. Frank’s influence over generations of Americans and people from all around the world is vast.

Born Francis Albert Sinatra, in Hoboken, New Jersey, on December 12, 1915. He is considered by many to be the greatest entertainer of the twentieth century. His recordings came to epitomize American popular singing at its finest, with a style that maintained fidelity to a song’s lyric and mood while imbuing it with subtle elements of jazz beat and phrasing.

A singer and entertainer since his teenage years, he was always in the spotlight. His distinctive voice and stage charisma accompanied him everywhere he went; he seemed to symbolize the American Ideal. In many ways, he defined the musical taste of the American middle-class, something that did not exist before WWII. He personified the hip adult persona. His tuxedos, suits, ties, hats, and the scotch he drank became synonyms for the good life in post-war America. People started to behave like him, dress like him, and dance to his songs. Most notably he was specific about his control over all aspects of his performance and image. He liked to be thought of as the boss, the man in charge. His pop-culture contemporaries such as Elvis Presley, Marlon Brando, and James Bond had their own charm, but none of then had come from a small town in New Jersey where the living was tough, where you had to fight to get to the top. The icon had been etched and gold-leafed for the world to see in a society before Vietnam, the civil rights movement, and women’s liberation changed forever the way we looked at entertainers.

During and after his performances, the suits and ties were also accompanied with another prop: alcohol. Bill Zehme, in an essay about the rat pack writes: “Frank learned to drink Jack Daniel’s from Jackie Gleason. “Mr. Gleason introduced me to a lot,” he says as proof that swagger can in fact be taught. Any man who drinks it is his friend. For ongoing replenishment, he likes the bottle in front of him, on a silver tray, with a rocks glass, a bowl of ice, and branch water for splashing. His first drink is always preceded by the tapping of glasses in toast.” (Zehme 2002) And yet, public display of libation notwithstanding, Sinatra always took care of himself and made sure that he would not get into trouble because of his drinking. Something that not many people realize when attempting to emulate his style. Here lies the paradox of Sinatra; Alcohol undoubtedly played a part in Sinatra’s performance, even in his real life, although he apparently knew when to stop. Although his orchestrated image may have been personally harmless, it becomes problematic when society does not know how to discern between what’s real and what’s make-believe and celebrities are often unwilling role-models. The link between real and make believe is increasingly difficult to differentiate in a world of reality-shows, docu-dramas, and news as entertainment.

The fascination of the audience with performers and their substance(s) of choice was not limited to Sinatra. There has been much speculation and lengthy prose about the other members of the rat pack and their drinking. However, like Sinatra, their risky choices may have been smoke and mirrors. When asked about Dean Martin’s drinking habits, Sinatra said, “Do you know that I spill more than he drinks?” Interestingly, in addition to being recognized as a talent from very early on in his life, Martin “dabbled in illegal activities, including driving liquor across state lines during prohibition, selling lottery tickets, acting as a bookie, and working as a card dealer and croupier in local gambling joints,” writes Zehme (Zehme 2002). And even though early exposure to risky behavior might have translated into substance use and abuse later, Martin’s adult drinking was mostly make-believe. Zehme writes: “He mostly sipped and pretended. Onstage, it was apple juice; you could tell by his timing, even more physically precise than that of… the former partner, Jerry Lewis.” However, after his career as a singer was over, and after the death of his son in 1987, he did become more of a recluse, seeking solace in the bottle.

Whether played out or real, the relationship between these entertainers and alcohol was influential, if not indicative of the America in which they lived. An America that historically sought substances to define itself, assert individuality, challenge norms, and explore the limits of freedom and civil rights. When Sinatra did it, it was carefully planned and controlled. Hank Cattaneo, his road manager, would say, “If inebriation comes, it rarely shows…There’ve been times, certainly when he’s feeling no pain, but he’s always lucid, always knows what he’s doing. The Italian word is figura, the figure – one must always maintain the appearance.” There’s another Italian phrase, perhaps a more significant one: con misura. Moderately. As in drink. Perhaps the best lesson young people can learn from Frank.

Comments on this article can be addressed to Gabriel Caro.


Zehme, Bill. 2002. And Then There Was One. In Intimate Strangers: Comic Profiles and Indiscretions of the Very Famous: Delta.