Cocktails With MAD MEN: The Old Fashioned

Welcome to a new series with Alamo Drafthouse beverage director Bill Norris! Learn the ingredients, history, social context and recipe for an Old Fashioned. 

“The three ingredient cocktail doesn’t lie.” Audrey Saunders, Pegu Club, New York.

In Season 3, Episode 3 of Mad Men, Don Draper leaps over a bar and prepares an Old Fashioned for himself and Conrad Hilton. It’s an expression of masculinity and capability, a Master of the Universe moment . The only problem is that the drink he makes isn’t really an Old Fashioned. It’s a bastardized version, popular in the 1960s, and a pale imitation of the real thing that has stubbornly persisted as the “right way” to make an Old Fashioned.


Prior to the early 1800s, your taverns and inns would have served punch by the bowl full; they would have served cobblers and slings, sangrees and flips, but order a cocktail and you would have received a blank stare from your bartender.

But on May 13, 1806, we find the first recorded definition of the word cocktail in the Balance and Columbian Repository out of Hudson, NY: “Cock tail, then, is a stimulating liquor, composed of spirits of any kind, sugar, water and bitters,” or the basic ingredients of what we know as the Old Fashioned.*

Over time, as bartenders stretched their wings and began to incorporate all manner of other ingredients into their cocktails, reaching for the vermouths and curacaos, the absinthes, the cordials and the whatnots of the back bar, that early mixture of booze, sugar, spirits and water, came to be called “An Old Fashioned Cocktail” by those who had no truck with the newfangled creations. Louisville’s Pendennis Club has long claimed they created the Old Fashioned, but it appears in print before they opened, and by 1880 there are references to people preparing and consuming Old Fashioned Cocktails made with spirits, sugar, water and bitters. As “cocktail” came to be the word that described any mixed drink, the Old Fashioned dropped “cocktail” from its name and commonly came to be made with American Whiskey as its base (except in Wisconsin where they stubbornly insist on a Brandy version), and the American whiskey of the time was largely what we now know as Rye Whiskey.


There are two basic ways to chill a cocktail: shaking in a cocktail shaker or stirring in a mixing glass. Uber cocktail geek and science nerd Dave Arnold goes into depth on the subject, but simply put, shaking is a violent action that dilutes faster and chills more quickly, while introducing air into the finished drink. Stirring, because it does not introduce a volume of air, allows the mingling of ingredients while maintaining a silky texture that is pleasing in the mouth. As a general rule of thumb, if a cocktail does not contain juice, it is best prepared by stirring rather than shaking, and your Old Fashioned will be better for the use of a bar spoon rather than a shaker.

We also need to understand the nature of sugar. Granulated sugar, either spooned or cubed, will not dissolve in a glass with spirits and ice, but if the sugar isn’t dissolved, your Old Fashioned is out of balance, with a slurry of sugar at the bottom of the glass. There are two solutions to the sugar problem, but one of those solutions has created a monster, where the drink becomes a pale shade of what it should be.


Things That Have No Place in an Old Fashioned: seltzer, soda water, ginger ale, sprite, mushed up fruit, sour mix, neon red cherries, citrus juice, orange slices, any kind of spirit other than your base choice.

An Old Fashioned is my baseline drink for an unfamiliar bar. If a bar can produce a quality Old Fashioned, I’m comfortable moving on to their cocktail menu or putting myself in the hands of the bar staff. But, more often than not, some or all of the above ingredients end up in the cocktail. No one is quite sure how or why the ubiquitous neon red cherry and the slice of orange ended up in a drink that doesn’t call for it (one theory is that prohibition era booze needed further masking than the sugar and water could provide, and it’s as good as any), but the addition of other liquids is largely an attempt to get around the stubborn science of sugar and alcohol.

The classic Old Fashioned preparation was to place some sugar in the bottom of an Old Fashioned glass, douse that sugar with a few dashes of bitters and add a small bit of water to the glass. Then, using a muddler, create a syrup in the glass, before adding your spirit and ice, stirring to chill and garnishing with a thin strip of lemon or orange peel. Over time, the orange and cherry slice found their way into the glass, the water got replaced first by soda water and later by other, sweeter things, in larger and larger quantities, until by the 1980s, you were lucky if your Old Fashioned even tasted of liquor at all.


For some reason, the Old Fashioned never truly died in Wisconsin. I don’t know if it’s because they drink a lot there, or because the winters are cold, but the Old Fashioned is ingrained in Wisconsin, and widely available and well made in spots one might not expect. Even though muddled fruit is widely used in Wisconsin, an “Old Fashioned, Hold the Garbage” ordered there will always be made in the historically correct way, and for that I am grateful to the good people of Wisconsin, despite their incorrigible drinking habits and inexplicable preference for Brandy over Whiskey in an Old Fashioned.


Ice is often overlooked, but, thinking about it, it’s a critical element in almost any mixed drink. It’s important to note that ice, when shaken or stirred, partially returns to its liquid form and that water is always an ingredient in what you are mixing.

We don’t add a large quantity of water to properly make an Old Fashioned, but it features prominently in the definition of the drink that spawned the Old Fashioned, and it is still critical. But we’re gaining that water, which will give us balance and drinkability from the ice that melts when we stir. Large, dense cubes are perfect for making an Old Fashioned. Seek out large ice molds for best results.


You can use any spirit you like to make an Old Fashioned. Dutch Genever is terrific. Brandy is nice for people in Green Bay. Vodka is pointless. Bourbon, especially over proof, can be swell. Gin, perhaps not, though who knows with all the new varieties of bitters on the shelf. Aged tequilas and rums can be interesting. But, really, you start with Rye Whiskey.

Canadian Whiskey is not Rye Whiskey. It once was made largely with Rye grain, but no longer. Canadian Whiskey, particularly that one in the fancy bottle with a purple velour bag, has less flavor than American whiskeys, can be adulterated with caramel and other flavors, and is largely not worth its expense. It’s a marketing triumph, but it will not make a good Old Fashioned.

I like bonded, or 100 Proof Rye. For everyday use, my favorite would be the Rittenhouse Bottled in Bond. It can be tricky to find. The inexpensive and widely available Old Overholt is not a bad substitute, but at 80 proof, you may need to adjust your recipe a tad. If you’re lucky enough to be able to buy Templeton where you live, it makes a nice drink indeed. Sazerac is also quite nice, but hard to find everywhere.


Back in the day, sugar was not nearly as refined as it is today. Molasses content was higher, the color was not white, and it was delivered in loafs. If you have a source for loaf sugar today, you’re a very lucky person indeed. Use raw or demerara sugar for the closest approximation we have to that old loaf sugar.

Or, if you’re lazy (like me) or will be making a lot of cocktails, use a rich simple syrup, made of 2 parts raw or demerara sugar to one part water. It’s worth it, it keeps in the fridge nicely for a bit and it makes your life easier.


2 oz Rittenhouse Bonded Rye (or your spirit of choice)
3 Dashes Angostura Bitters
½ oz Rich Simple Syrup

In an Old Fashioned Glass, combine Rye, simple syrup and bitters, add a large ice cube or two and stir until quite cold. Cut a swath of peel from a lemon or orange and express the oils over the glass, dropping the peel inside the glass for garnish.


*For Further Reading on the early history of American drinking, please read David Wondrich’s remarkable Imbibe! & Punch: The Delights (and Dangers) of the Flowing Bowl