Some would say that the Old Fashioned is the most ancient of concoctions. (photo by Brent Hofacker)

In my days working the stick, concocting an Old Fashioned was one of the labor-intensive drink orders I was always delighted to make.

I mean, a mojito is a fine drink, but for a bartender, the effort is rarely worth the final result. When you order an Old Fashioned, you are ordering a quaff with more than a little history. “Old Fashioned” is short for “old fashioned cocktail,” and may, in fact, represent the original American cocktail (the Sazerac is a stiff competitor for the title, but read on and you will see how their histories dovetail). Early 19th century references pegged a “cocktail” itself as a potent mix of spirits, water, sugar and bitters.

1880s Chicago seems to be the origin of the Old Fashioned as we know it; a whiskey-based drink. Its popularity, however, may have started at the private Pendennis gentlemen’s club in Louisville, KY, near the turn of the past century, where a barman crafted the drink in honor of distiller James E. Pepper, who requested the recipe on his travels. Pepper often visited New York City and bent elbows with other captains of industry at the fabled Waldorf-Astoria Hotel. And from this elevated base of operations, word spread. Undoubtedly, the Pendennis version used bourbon-style whiskey as its base, but in the years before Prohibition, the development of the Old Fashioned would have been built more on rye whiskey, much more dominant at that time. So, show some respect: you are ordering a glass of national history, and, for me and many others, you are ordering a piece of personal history, as well.   

I don’t think my grandfather was much of a drinker. My mother’s family owned and ran a very small lakeside marina business in New England, and I imagine my grandfather enjoyed an occasional cold beer after a hard day. As the business started doing well, Grampy would sometimes take us all out to a “nice steak dinner,” and he always started that ritual with an Old Fashioned made with Seagram’s V.O. Canadian whiskey. As such, that Old Fashioned was probably the very first cocktail I was allowed to take a quick sip of. This wasn’t snuck down when the adults were in the bathroom or something; it was offered to me by my grandfather, and I remember liking the whole deal, including the plastic sword cocktail pick.

Grampy wasn’t much of talker either, but later on, and after I’d done some bartending work, I remember discussing his cocktail of choice and offered to make him one on the spot. He opened up a kitchen cabinet with a multitude of boxed bottles of Seagram’s V.O. he had gotten as gifts over the years, all of them unopened.

My recipe below is based on his preferences and direction, and strays somewhat from the traditional Old Fashioned recipe. It’s delightfully sweeter and fruitier than a classic version. But this is how my Grampy—and, undoubtedly, many thousands of others of his generation—liked them:


1 hefty rocks glass

(One of the beauties of the drink is that it doesn’t require a cocktail shaker or strainer; you build the drink in the glass. Just make sure the glass can stand up to some pressure.)

A wooden drink muddler, or equivalent

(A traditional drink muddler looks like a small baseball bat, but I’ve carefully used a hefty wooden knife handle as a successful substitute.)

A cocktail pick

(Preferably, ideally, a little plastic sword.)


2 sugar cubes

(You can use granulated sugar or even simple syrup in a pinch; but it just won’t be as good.)

Angostura bitters

(Enough to saturate the sugar cubes.)

1 small orange

(You’ll need a 1/8 wedge for the drink and a thin slice for the garnish.)

Ice cubes

Seagram’s V.O. blended Canadian whiskey or equivalent

(My grandfather came of age during Prohibition, and Canadian whiskey, illegally transported, would have been the most common spirit for this drink at that time. Good news is, as Canadian whiskeys tend to have a strong rye component and flavor, they are also a terrific choice for an Old Fashioned in general. After the break-up of Seagram two decades ago, the V.O. product is now part of the portfolio of closely held U.S. spirits conglomerate, The Sazerac Company. Bourbon or American rye, of course, work well, too.)

Maraschino cherries

(Real ones if you can get them, or standard candied cherries in a pinch. Real maraschino cherries are usually a product of Italy from companies like Luxardo and are smaller and darker—and taste better—than the neon-red condiments that are more common in the U.S.)

Club soda

(For a splash, if preferred.)

  1. Place two sugar cubes in a rocks glass and shake enough Angostura bitters onto them to saturate.
  2. The classic recipe calls for a bit of water to help dissolve the sugar cubes, but try this: place a 1/8 wedge of a small orange in the glass.
  3. Muddle (smack, grind and otherwise crush) the orange wedge and cubes, breaking up the cubes, releasing a bit of orange juice into the glass to help dissolve the cubes and expressing some of the orange peel’s zesty oils. Orange juice is less effective than water for dissolving sugar, so you will likely have some sugar chunks left, and this is a good thing. If you have real maraschino cherries, add a drip or two of the syrup to the glass before you muddle, as well.
  4. Remove the remains of the orange wedge (or leave it) and fill the glass halfway with ice cubes.
  5. Add a liberal pour of Seagram’s V.O. or your preferred substitute. You want the ice cubes to float, so probably abou two 1.5 oz shots.
  6. Top up with a splash of club soda (optional, but recommended.)
  7. Arrange a maraschino cherry and a thin orange slice on a cocktail pick. Submerge the garnished pick and give the drink a short stir.
  8. Pull the garnished pick out and lay across the top of the glass to drip-dry for a second.
  9. Contemplate the garnished pick for a moment, then pass over  to your grandson or a suitable substitute to enjoy.
  10. Start sipping.

This recipe appears in honor of Henry Winfield Heaton.