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Frank Sinatra: Daily Routines, Habits, Rules, Advice: On Drinking

Posted by Colonel Bourbon on

"What would Frank do?"

The Way You Wear Your Hat by Bill Zehme, published in 1997, is about how Frank lived his life, his daily routines, off and on the stage. As the front cover says, it's the "Lost art of living." 

Frank Sinatra Daily Routines Habits Rules Advice On Drinking

(You can find “Frank Sinatra The Way You Wear Your Hat” on Amazon.)

The book grew out of a profile of Sinatra in Esquire magazine in 1996. The book is, as the dust jacket flap suggests, "perhaps the most comprehensive access to the world of Sinatra, now fully realized in these pages."

The author wrote: I wanted to ask him essential questions, the kind that could save a guy's life. I wanted what might approximate Frank's rules of order."

Night Owl

When we say daily routines we mean after the sun goes down, when the day really got started. He never recorded a song until at least after 8PM.

A doctor once asked Ole Blue Eyes how he felt in the morning after drinking so much Jack Daniels?

"I don't know, I'm never up in the morning,"  was the reply.

What was it like to hang with Sinatra,  as he held court at his favorite restaurants and bars, past midnight and into the early hours of the morning. "He would break more dawns than most mortals." "Look at the colors," Sinatra would say at dawn, the tint of the sky being what he called "Five O'Clock Vegas Blue."

Steve Lawrence: "I told him he's probably the last of the Italian vampires." But here's how Sinatra did it: A secret: he took power naps.

The chapters of the book, designed in a swinging style, with many photos and quotes, are each on a different subject: The night owl chapter is called: "The Wee Small" (named after the song/studio album In the Wee Small Hours released in 1955), with the subtitle "The Leader After Dark. Other chapters are about "Ring-a-Ding-Ding" (You gotta love livin' baby! Because dying is a pain in the ass!). There's also his "Pallies," "Drinking Again," "Style," "Broads," "Love and Marriage," and of course "My Way." (He never really liked that song; he felt it was too "self-praising."

"Booze and Smoke: Drinking Again"

Since the Colonel Bourbon blog is about t-shirts about America's whiskeys, and Frank drank a lot of it (and a lot of other stuff), this review will dive into the chapter on the drinking :)

Jack Daniels Dean Martin Sammy Davis Junior Jackie Gleason

 (The chapter on the Chairman of the Board's drinking preferences. Spirits come up throughout the book, of course.)

Legend says that Sinatra was introduced to Jack Daniels by Jackie Gleason at Toot's Shor's, their usual haunt in New York. If you Google how Frank discovered the Tennessee whiskey, that is what you will usually find. (In fact, before we read this book, we were under the same impression.) But this book, with its attention to detail, says their tab debt had "ballooned perilously," so that night they went to a joint called Harlequin.

"I feel like getting smashed," Sinatra said. "Now what's a good drink?"

Gleason bellowed "Jack Daniels! That's a good place to start!"

This anecdote is earlier in the book, setting the tone of the tales. 

In the chapter on booze, we learn specifically how he liked his "gasoline": "Always three or four ice cubes, two fingers of Jack Daniel's, the rest water, in a traditional rocks glass.

He liked to let it sit for a while, "he wanted to let the flavors blend."

And he wanted a bowl of ice on the table, to keep the drinks chilled, with tongs or a large spoon. He did not want fingers to touch the ice in the drinks.

He never wanted a water-back (a glass of water with his drink). "... the mere notion appalled him.  If a waiter placed a glassful before him, he would snap "What's this! I'm thirsty, not dirty. Take it away. Now."

In fact, he was decidedly not a fan of plain water. He joked that he showered with club soda!

If you were drinking with him, and he said it was time to trade some ice cubes, that was his bonding ritual. Or you'd exchange an olive. "This was something of a sacred act."

He drank other things. "whenever he wanted to give  his Daniels a rest, he turned to vodka, Stolichnaya specifically. He always drank it on the rocks, except in martinis, which were always cold and very dry."

"His perfect martini: Stoli or excellent British gin, well stirred or shaken in ice, with the tiniest drop of vermouth, served in cold glass and crowned by two olives." He drank martinis only before dinner, never during or after, and rarely more than two." Bloody Marys were a favorite afternoon drink.

Warm vodka? "There's nothing worse."

He didn't like white wine. He loved red. 

"Hangovers feared him. His metabolism knew no such thing. 'He doesn't get hangovers -- he gives them."

Some of it was for show. On stage, the scotch in Dean Martin's glass was often apple juice. And the Chairman of the Board told his daughter Nancy a technique he sometimes used at parties. He'd take a few sips and put his glass down somewhere and walk away. "...They give you another drink and they think you're drinking a lot.

But make no mistake, drinking was routine par for the course, just as the way he wore his hat.

His list of 1980' New Years resolutions, which he read on stage at Caesar's Place in Las Vegas included:

"Give up drinking all day on February 30." 

(You can find “Frank Sinatra The Way You Wear Your Hat” on Amazon.)

Here's Dennis Miller about the time he had dinner with Sinatra and his crew.

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  • I was surprised to learn Sinatra’s favorite color was orange. And woe to the “Harvey” who wore brown after sundown! This book was a “gas”!

    Jonathan Van on

  • I love this book. Behind the scenes with details and memories I haven’t read anywhere else. A good read. Thx for the recommendation!! Miss you Frank.

    Michael on

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