Sinatra’s Favorite Drink

Have it Frank's Way on his birthday

Your cocktail calendar entry for: December
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Today we’re mixing up Frank Sinatra’s favorite drank and doing it just the way he did.  Why?  Because December 12 is his birthday.  One of the all-time great drinkers, Francis Albert Sinatra was born in 1915 to Italian immigrants in Hoboken, New Jersey.  Today we’re mixing Jack Daniel’s set up in a way called Frank’s Way, or what is sometimes known as the 3:2:1.

Frank Sinatra’s background

We’re talking about  Ol’ Blue Eyes himself, one of the best-selling music artists of all time, selling more than 150 million records worldwide.  That’s pretty good for a guy who never learned to read music, had an ear drum permanently perforated at birth and who started by belting out songs for spare change while sitting atop the player piano in his parents’ tavern in Hoboken.

He could sing alright and knew a bit about living life well.  This included visits to many bars – drinking, carousing with the Rat Pack and holding court.  He was such a beloved regular that he had his own chair or barstool at some watering holes.  He was known for dispensing nuggets of wisdom such as:

“You only go around once, but if you play your cards right once is enough,” or the better known “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.”

Those are wise words so it’s no wonder he was considered Chairman of the Board of the Rat Pack after the death of the group’s founding leader, Humphrey Bogart.  And he led, alright, once ordering 300 Bloody Marys from room service for a Rat Pack party.  You know, the Rat Pack:  Frank, Sammy Davis Jr, Dean Martin and so on.

What was Sinatra’s favorite drink?

Sinatra with Jack DanielsEven before the Rat Pack existed Frank got a tip in 1947 from the comedian Jackie Gleason.  That tip was simple: Jack Daniel’s.  Then Frank carried a rocks glass of whiskey onstage sometime in 1955.  There he uttered the line “Ladies and gentlemen, this is Jack Daniel’s and it’s the nectar of the gods.”

That was a life changing event, not so much for Frank who was already established as a dedicated whiskey drinker, but for Jack Daniel’s.  Prior to that time it was really just a small regional brand and not the best-selling whiskey in the world that it is today.  But it really was Sinatra’s favorite drink, and he had a bottle buried with him when he died in 1998.

Indeed, Frank Sinatra ended up being Jack Daniel’s first real brand ambassador even though such a term was unknown at the time.  It’s not as though Frank couldn’t afford all the sauce he wanted –right after WWII he pulled up to $93,000 a week just for a busy radio appearance schedule – but Jack Daniel’s knew a good thing and made sure his glass was never empty.  Even with the whiskey on allocation because Frank’s endorsement had driven demand through the roof the company made sure there was always a case in his dressing room wherever he went.

He made Jack Daniel’s look like a companion.  Here’s Frank stepping out on to the roof of the iconic Capitol Records building in Hollywood, favorite drink in hand.  As you might guess we’re going to prescribe Jack Daniel’s as Drink of the Day, but if you’re more bourbon oriented we’d suggest the Rat Pack Manhattan.

The Sinatra Burger

As a side note, in 1967 actress Dinah Shore put together a celebrity cookbook named Cooking With The Stars. Dean Martin and Frank both submitted recipes. Both are classics but Frank’s is generally regarded as better:

Martin Burgers:

1 lb. ground beef
2 oz. bourbon – chilled

Preheat a heavy frying pan and sprinkle bottom lightly with table salt. Mix meat, handling lightly, just enough to form into four patties. Grill over medium-high heat about 4 minutes on each side.

Pour chilled bourbon in chilled shot glass and serve meat and bourbon on a TV tray.

Sinatra Burgers:

    1. Call Deano.
    2. Tell him to make you a f****n’ burger.
    3. Drink his bourbon.
How to make Sinatra’s favorite drink:  the 3:2:1

Enough of this fun.  Let’s get to Sinatra’s favorite drink, the way he did it.  As you might have guessed by now it involves Jack Daniel’s whiskey. To have it as he did we’re going to mix a Frank’s Way, also known as “The 3-2-1” As usual, nothing other than ordinary pantry supplies and as simple as it gets.  But there are a couple of things to note.

First, you’re probably familiar with seeing Jack Daniel’s Old No. 7 on the shelf.  Unfortunately, at 80 proof (40% alcohol) it’s below the original 90 proof Frank was drinking.  Yes, you can spend a small fortune for a bottle of their Sinatra Select brand, which is bottled at 90 proof.  But instead of doing that we recommend getting a bottle of the recently released Jack Daniel’s Bonded Tennessee Whiskey.  When you see “bonded” on a liquor bottle it means it’s 50% alcohol.  It’s a good choice here as it’s good for both drinking like Sinatra and as a base for other mixed cocktails.

Second, Frank preferred to simply refresh his drink by adding ingredients as needed rather than pouring an entirely new drink.  Follow his way.

Finally, you should clearly want to channel your inner Frank Sinatra and belt out your own renditions of a few of his tunes.  Go ahead, break out the dusty karaoke machine in your closet.  If you don’t yet feel like that it just means you haven’t followed the preceding notes to a sufficient degree.  So get to it.

sinatra favorite drink

Frank’s Way

Drinking like Frank Sinatra is about the easiest thing possible since all it requires is a bottle of Jack Daniels, some ice and a glass. We should note, though, that the splash of water called for in the original is recommended only when you're using the Jack Daniel's Bonded whiskey. If you're using the old No. 7 version, which is notably lower proof, we'd leave it out.
5 from 1 vote


  • Old Fashioned Glass


  • 1 bottle Bourbon (specifically, Jack Daniel's Bonded, not the regular No. 7)


  • Place 3 rocks into an Old Fashioned glass.
  • Pour 2 fingers of Jack Daniel's. For those of you too embarrassed to ask what that means it’s poured to the depth of two finger widths from the bottom of the glass.
  • Add 1 splash of water (optional, recommended only with Bonded whiskey.)
  • Drink.
  • Start singing Sinatra tunes.


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