Frank Sinatra’s Drink of Choice


The myths of the Rat Pack, headed by Legend Frank Sinatra run rampant. Who knows how many were true, what is fact and which is fictional, and which is overly embellished. We all know that Sinatra and his Rat Pack were drinkers and smokers with the exception of Joey Bishop. The question is, what did he actually drink?  Us cocktail aficionados want to know!  Especially of of us who are very much into vintage retro culture.

So, from a tweet from the daughter and retro icon herself, Nancy Sinatra informed me that he had “Jack Daniels, with water and 3 ice cubes”.  Simple enough, so I tried it, 2 parts Jack Daniels, 1 part fresh cold spring water and about 3 ice cubes, I don’t know the size, but it was bout 50% of the space in the glass.  Honestly, a bit bitter, the water takes away the sweetness from whiskey made from corn mash, or even any spirit in my opinion), and as much as I love bitter, I like my bourbon sweet, so for me, I’d drink it right over the rocks (or ice), even when it melts, its nice and cold but still sweet.

Sinatra called bourbon “The perfect gentleman’s drink” and I would agree, though I know he also loved Martinis.  But to be clear, (and for all you idiots who call me an idiot), Jack Daniel’s is classified as a Tennessee Whiskey, not Bourbon.  And, if I were bartender and Frank Sinatra came in and asked for Jack Daniel’s Bourbon, I wouldn’t dare correct him, and I would certainly have more interesting topics of conversation to discuss if he were willing.  The truth is, what Jack Daniel’s made and what Frank Sinatra drank half a century ago probably is a very different product than today.  Remember, it was actually Sinatra who popularized Jack Daniel’s.  Years later, to keep up with production, they changed it from 90 proof to 80 proof and it became a more consistent controlled product, but from there, we can’t pretend to know what the distillery was producing then or how the batches of barrels were produced.  Only they know, and I can promise you, Sinatra was just drinking, not not bickering about how to classify this whiskey.

Now Sammy Davis Junior liked Jack Daniels with Coca-Cola – this is also very delicious, and a bit sweeter and cut the taste of the bourbon but not so much you could not taste.   The classic Jack & Ginger was of course JD and ginger ale.  Not sure who drank that, but I am almost certain Dean Martin liked his whiskey straight, and it was not bourbon and did not have any mixer other than chilled and straight up.

It is said that the Legendary Frank Sinatra was actually buried after death with a small bottle of Jack Daniels with him.  So no matter how you drink it, remember, its a classic, like Sinatra, and you should at least try it several different ways.  By the time you empty the bottle, you will have had something you loved, and what is especially nice, is that you experience the very same things legends loved.  They are simple, they are fine, and even if you hate it, its something that you have experienced and as close as you will get to walking in their shoes, even for just 1 happy hour.

Jack Daniel’s is more sweet than bourbon, but they make something even sweeter known as “Honey Jack”, which in my opinion is nothing even close to whisky.  To me, it tastes like some caramel-sweetened liquor with a whiskey base. Last time I checked, it is ironically more expensive than Jack Daniels #7 – to each their own, however, either way, I am a purist and all for the original, especially if I am tasting the same thing other legends were drinking and tasting.

This Blog Entry was Re-edited April 23, 2014 – I never intended this to be a debate about whether it is a bourbon, a whiskey and/or a definition of anything else.  It was simply what Frank Sinatra enjoyed drinking, not what he called it or what its officially classified as. For anyone who is a true Sinatra fan, they certainly know he would sooner entertain trivial terms like calling it pasta “sauce” or “gravy” a million times before ever ignoring or arguing if it’s Tennessee Whiskey or Bourbon.


7 thoughts on “Frank Sinatra’s Drink of Choice

  1. As long as the spirit is distilled according to the laws (made from 51% corn mash; cut with only limestone filtered water from kentucky, etc), it can still legally be called bourbon – but in an ever-industrial age, many distilleries are not shipping the spirit to facilities which are outside the state of Kentucky. Its still legally bourbon, it still technically bourbon and anyone sitting down to one distilled or bottled in Kentucky as opposed to Virginia can never taste the difference. If they can, its simply because one is from a different year, or aged in an oak cask with wood from a different tree. Its not unlike wine in that sense… batches will vary from year to year or even still to still.

  2. Federal law may classify it as a bourbon but the company disagrees with you:
    From their official site.

    Is Jack Daniel’s a bourbon?
    Jack Daniel’s is not a bourbon – it’s a Tennessee Whiskey. Jack Daniel’s is dripped slowly – drop-by-drop – through ten feet of firmly packed charcoal (made from hard sugar maple) before going into new charred oak barrels for aging. This special process gives Jack Daniel’s Tennessee Whiskey its rare smoothness. It’s this extra step – charcoal mellowing – that makes Jack Daniel’s a Tennessee Whiskey.

  3. Bourbon is the United States only native spirit. It can only be from the United States. Bourbon aficionado s are quick to correct someone who mistakes JD for bourbon. Bourbon can take on pretty much any taste depending on the mash bill, what the predominant grain is, length of time aged in a new oak barrel (another by law is it has to be a new charred oak barrel) and the proximity of where the barrel is aged in the rickhouse. Kentucky has been so successful at making bourbon because of certain major factors. A good bourbon will have a good natural limestone deposit. Kentucky has one of the largest deposits of it. The limestone is what really brings out the sugars and yeast in the mash. Limestone water is also very good for your bones. Another reason we’re the mecca for throughbred horse breeding & racing. Our weather is another factor in the characteristics we have in our bourbon. Extreme summer heat & winter cold lends itself to the extraction of liquid mingled ng with the wood in our barrel s. I worked for a time at Buffalo Trace Distillery. Its the most award winning distillery for bourbon in the country. A fact that we dont take for granted and are very proud of. The market for bourbon has become dilluted with the popularity of bourbon sky rocketing. My advice for a novice bourbon drinker is give our spirits a try first. When properly instructed on how to distinguish the nose, taste & finish of a bourbon you will discover its quite a art. I apologize JRCX for the attacks from of the somewhat misinformed others critiquing your article. A true bourbon lover will educate you in a gentleman manner. Which led me to your article about the great Frank Sinatra. I recommend if anyone is in the Kentucky area take the time to visit some of our distilleries. Promise you they will be some of the most beautiful places you’ve sern.

  4. I hate to break it to you, but Jack Daniel’s meets all the legal requirements to be called a bourbon; JD and Brown Foreman simply CHOOSE not to call it such as a marketing distinction (as evidenced by their official faq quoted above by Mr. Davis). But to argue either way is to belittle the point…Jack is a pretty good American whiskey, and the best- or second-best-selling whiskey in the world, depending on whose accounting figures you want to believe.

    I recently watched a youtube video of Mr. Sinatra’s celebrity roast, and he had a couple of glasses in front of him, and 2 bottles of ginger ale. Begs the question as to whether he preferred his Jack mixed with ginger, at least while onstage. It has been documented that many of the Rat Packers would dilute their alcohol onstage to give the appearance they were hard-drinkers but maintain necessary control when needed (and, yes, I am thinking specifically of Dean Martin).

    • You are 100% Correct. I had many criticize me on this post that it was not bourbon, but it can legally be called bourbon. There are still some out there that believe and insist that if its not made in Kentucky it cannot be called bourbon which is also false. Thanks for your input!

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