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    Home » Classic Cocktails » How to Make The Easy Frank Sinatra 3-2-1 Cocktail

    Published: Oct 2, 2023 · Modified: Oct 26, 2023 by Kevin Mayfield · This post may contain affiliate links.

    How to Make The Easy Frank Sinatra 3-2-1 Cocktail

    Jump to Recipe Print Recipe

    Great artists have a way of distilling things down to their essential elements to focus on perfection, and the Sinatra 3-2-1 is a great example of that principle. Frank knew that nothing should get in the way of the taste of a great whiskey!

    A rocks glass with Jack Daniels Sinatra Select whiskey.
    A fine whiskey and a splash, just like Frank himself used to enjoy.

    The Original 'Influencer'

    Back in the mid century era, there were just a select few celebrities that transcended their fields. In 1955 no one was a bigger celebrity than Frank Sinatra. Born on December 12, 1915 in Hoboken, New Jersey, Frank was a hit singer and an Academy Award winner for his performance in From Here to Eternity. He was one of the first true global superstars, and people loved the cool lifestyle that he, Dean Martin and their Rat Pack pals lived. So when he walked onto a concert stage in New York City with a rocks glass filled with an amber liquid and announced "This is Jack Daniel's, and it's the nectar of the gods," it caused a mad buying rush from New York to southern France.

    Frank Sinatra pouring Jack Daniel's whisky into Dean Martin's glass.
    Here's Frank himself making a 3-2-1 for Dean Martin while Sammy Davis Jr looks on int the great photo by Michael Ochs.

    Introduced to Jack Daniel's by his buddy Humphrey Bogart, Frank's recommendation caused a problem for the company. At the time Jack Daniel's whiskey was just a small, regional distiller and not the global brand we know today. Frank's endorsement naming Jack Daniel's as the best whiskey caused a run on their whiskey, and they nearly ran out of it. He was not a paid spokesman, he just liked it. Being smart business people, the good folks at Jack Daniel's always made sure to ship a case to wherever Frank was appearing--whether it was in Las Vegas or Chicago. Upon his death in 1998, Frank Sinatra was buried with a bottle of Jack Daniel's by his side.

    Is the Sinatra Select Really Different From Regular Jack Daniel's?

    Commemorating what would have been Ol' Blue Eyes 100th birthday, for the first time the makers of Jack Daniel's and the Sinatra family issued a special batch of whiskey limited to only 100 bottles. A few years later, they reissued it in larger quantities. What makes this whiskey different than regular Jack? Special oak barrels that have extra deep grooves cut into the white oak so that the mash comes into more contact with the wood. These became known as the Sinatra barrels. This gives the extra dark whiskey a more oaky, woody flavor. This is what Jack Daniel's tasted like back when it was a favorite of the Rat Pack, and makes a good whiskey into a great whiskey.

    Ingredients for the Sinatra 3-2-1

    There are only a few things needed for a Sinatra 3-2-1. Frank always liked to keep it simple, and this is the easiest of cocktail recipes. You just put 3 ice cubes in a rocks glass, pour in two 'fingers' of Jack and add a splash of water.

    There are many old fashioned bartending terms that are no longer commonly used. A 'finger' of whiskey is one of them. It refers to a time when you would hold a finger horizontally around the bottom of the glass and pour to the top of your finger. Was it consistent and repeatable? Not at all, which is probably why it eventually fell out of common use. To be more precise, one finger is approximately ¾ of an inch of whiskey in a standard old fashion cocktail glass, or about one ounce, thus making Frank's "two finger" serving roughly two ounces.

    Keep in mind that this is a very pure whiskey drink with a bold character and can be seen as a bit more harsh than a traditional mid-mod cocktail like an Old Fashioned. However, once you are used to it, you can really appreciate the incredibly smooth vanilla finish and rich amber color.

    Tips for Success

    There's no way to mess this one up! There is no need for simple syrup, bitters or orange peel. You don't even need a cocktail shaker!

    • Regular Jack Daniel's is fine to use, but if you can, find a bottle of Jack Daniel's Sinatra Select Tennessee whiskey. It really does make a difference in taste, although it can be hard to find.
    • Rather than regular tap water, use a splash of Kentucky Mixing water to bring out the pleasant smokiness of the whiskey--this is the best way to enjoy a glass of Jack Daniel!

    Do you have a favorite Frank Sinatra song to sip a little whiskey while listening along? Mine is Summer Wind.

    If you're looking for more classic cocktail recipes, try James Bond's Vesper Martini, The Rat Pack's Classic Manhattan Cocktail, and Ernest Hemingway's favorite Daiquiri Recipe.

    Before you go, did you try this cocktail? Why not leave a comment in the Comments section along with a rating? I always appreciate hearing from you and getting your feedback.

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    A closeup of a whiskey in a rocks glass

    How to Make The Easy Frank Sinatra 3-2-1 Cocktail

    This simple whiskey drink was Frank Sinatra's favorite way to enjoy Jack Daniel's.
    5 from 4 votes
    Print Recipe Pin Recipe
    Prep Time 1 minute min
    Servings 1 Cocktail
    Calories 130 kcal

    Equipment

    • 1 Rocks Glass
    • 1 Jigger

    Ingredients
      

    • 2 oz Jack Daniel's Whiskey (Use Sinatra Select if you can find it.)
    • 1 splash Water (Use Kentucky branch water if available.)

    Instructions
     

    • Simply place 3 ice cubes in a rocks glass, pour in the whiskey and add a splash of water.

    Notes

    Sinatra drank this cocktail without garnishments; none are needed!

    Nutrition

    Serving: 2ozCalories: 130kcal
    Tried this recipe?Let us know how it was!

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    Nancy and Bentley

    Hi, I'm Nancy! Welcome to Flourchild where I share classic mid-century recipes from the 1940's - 1970's. I feature many vintage handwritten recipes, and provide modern shortcuts and a variety of healthy and special diet-friendly versions whenever possible. Join me in exploring the delicious flavors and from-scratch cooking techniques of our past!

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