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Frank Sinatra and Jack Daniels

Posted by Colonel Bourbon on

The story goes that Jackie Gleason introduced Frank to Jack at Toots Shor bar in New York. It was love at first taste.

Frank Sinatra and Jack Daniels

Old Blue Eyes never called it Jack; it was always Daniels or J.D. Technically, J.D. can be called a bourbon but the Jack Daniels company will have none of that Kentuckian talk, It is, they insist, a Tennessee whiskey. “… it’s dripped slowly – drop by drop—through ten feet of firmly-packed charcoal (made from hard sugar maple) before going into charred oak barrels for maturing.”

Before discovering “Daniels,” Frank regularly drank Chivas Regal in the 1950s. And whiskey was not the only juice he drank. Ava Gardner, said: “Every single night, we would have three or four martinis, big ones in champagne glasses, then wine with dinner, and then go to a nightclub and start drinking Scotch or Bourbon. I don’t know how we did it.”

 Frank Sinatra and Eva Gardener

(With wife Ava Gardener, 1951. A passionate, tumultuous relationship.)

So when Frank Sinatra sang this:

“I Get a Kick Out of You”

I get no kick from champagne.

Mere alcohol doesn't thrill me at all.

So tell me why should it be true

That I get a kick out of you?”

 It wasn’t entirely accurate in real life.

"That's not my sport."

Frank was very particular about how he liked his “Daniels”: a two-finger measure with three or four ice cubes, plus water, in a traditional rocks glass.

Once, when he was served a glass of Jack Daniels filled to the top with ice, he removed the ice, leaving only four cubes. Bill Zehme wrote in The Way You Wear Your Hat: Frank Sinatra and the Lost Art of Livin’: ‘The bartender asked: “Is there a problem, Mr. Sinatra?” Quietly, he explained: “No, but with all this ice, I figured we’re supposed to go skating here or something. That’s not my sport.”

And he hated drinking water, at least by itself. Because “fish f*** in it,” he said.

He supposedly once admitted to a doctor that probably consumed a bottle of Jack a day. The doctor said: “My God, Frank! How do you feel in the morning?”

“Hell if I know, doc,’ Sinatra replied. “I don’t get up ‘til the afternoon.”

 Some of his other booze-soaked quotes:

  • “I feel sorry for people that don't drink because when they wake up in the morning, that is the best they’re going to feel all day.”
  • “Alcohol may be man's worst enemy, but the bible says love your enemy.”
  • “Basically, I'm for anything that gets you through the night—be it prayer, tranquilizers or a bottle of Jack Daniel's.”

Frank Sinatra was also very meticulous about his clothing. U2’s Bono told a story of a chat he had with him, where the singer quipped, that with all the success U2 has been having, they haven’t spent anything on clothing. We like to think bourbon and whiskey tshirts  might catch the eye of Ol’ Blue Eyes with the quality of our tees. The Bourbon Whisperer tee, perhaps.

"My Dinner with Sinatra"

There's a wonderful article in which the author sits down to a course of Sinatra's favorite dishes at his favorite restaurant, Patsy's on West 56h Street. It is said that when he was on the outs with his career and all alone on Thanksgiving, Patsy's proprietor Joe Scognamillo opened up his place so Frank could have a meal, and filled it with guests corralled at the last minute, so Frank would have company.

In honor of Sinatra's birthday, December 12, 1915, the author cooked the crooner's favorite dishes from Patsy's using Patsy's Cookbook. The dishes were:  "Clams Posillipo, Stuffed Artichokes, Arugula Salad, Fusilli with Garlic and Anchovies, Veal Cutlets Milanese and, for dessert, Lemon Ricotta Torte."

The author noted the Cookbook's comments some of Ol' Blue Eye's food preferences: meatballs should be made with veal; not too much garlic on anything; keep the veal cutlets thin --  and you can always judge an establishment's food by the tomato sauce. He told his daughter Nancy, "When you go to a new Italian restaurant, you should always try pasta with tomato sauce first. If the sauce isn't good, the rest of the food won't be either." 

The author, who goes by the nom de plume "Mister Meatball," imagined what the dinner conversation with Mr. Sinatra might be. He and his friends came up with some possible questions. His was: Before we crack open another bottle of Jack, would you mind singing  for me "East of the Sun", with the twice-repeated coda at the end?"

Jack Daniels Sinatra Selection

In 2012, Jack Daniels released the Sinatra Select:

"Made with our unique “'Sinatra Barrels' that have deep grooves specially carved into their staves to expose the whiskey to extra layers of toasted oak. This added exposure imparts a rich amber color, bold character, and pleasant smokiness, punctuated by an incredibly smooth vanilla finish. Much like Frank, this Tennessee Whiskey is one of a kind."

Adding grooves into the barrel staves in an interesting, still rather unique idea. Jefferson's Twin Oak does this.

We wonder what Sinatra would have thought his namesake whiskey.

 (Published by Colonel Bourbon)

1 comment

  • I am typically a straight Kentucky Bourbon guy!!! I like it one way…. NEAT!!! IN A GLASS…. THAT’S IT!!! I’ve drank Jack but always perfered a top shelf KY Bourbon such as Bookers, Bakers, Woodford, and on the low end Makers Mark or Knob Creek… But Jack Daniels Sinatra is hands down the very best whiskey I have ever consumed in my life!!!

    Mack Ginn on

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