Getting Old-Fashioned with Robert Simonson and His New Cocktail Book

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old fashioned daniel krieger
Credit: Daniel Krieger

When it comes to digging deep into the heady history of cocktails, Robert Simonson isn’t afraid to plunge a toothpick to the bottom of the glass for a cherry of an answer. You might say his careful curiosity makes him the best sort of reporter, engaging his subjects with measured Midwestern manners and Wisconsin ex-pat-born patience and practicality. A dapper barfly happy to bide his time until a story gets poured out. We have been really lucky to have this curious quaffing creator of man-on-a-barstool stories pen numerous glimpses into both New York’s bar and distilling worlds, so we were really excited to get our hands on a copy of his new book, The Old-Fashioned (Ten Speed Press).

We caught up with him at last week’s Tales of the Cocktail after his duo of seminars on the topic, and here’s what he had to say about the world’s oldest cocktail, fruit salads, John Wilkes Booth and his mom’s favorite drink:

Edible Manhattan: You come out swinging in this, saying the Old-Fashioned is really the oldest cocktail. How’s that work out?
Robert Simonson: Well, the drink’s full name, technically, is Old-Fashioned Whiskey Cocktail, which gives you a better idea how old the drink is. The Whiskey Cocktail dates back to the early part of the 19th century, easily beating the Martini, Manhattan and other classic cocktails in age. There are other kinds of drinks that we now think of as cocktails that are older, such as the Julep, which dates to the mid 18th century. But — and I’m being very cocktail-geeky here — they are not technically “cocktails,” as the category was once strictly defined. That is: spirit, sugar, water, bitters.

EM: I had a social studies teacher in high school who said that when you read great literature, it’s a mirror to what was going on in history at that time. Do you think you can apply the same logic to drinks and the creation of them?
RS: The cocktail historian David Wondrich once told me that one of the best ways to research what people were drinking during a certain time period is not to look at old cocktail guides, but to read newspapers and novels from the time. I agree with that idea. I learned a lot about the history of the Old-Fashioned through old newspaper articles. However, I don’t know many novels that the Old-Fashioned plays a big role. It played a part in Rabbit, Run by John Updike, but it was not a flattering one. The title character’s wife self-medicates herself with them. But those were the days of the drink’s nadir, when it was possibly the least cool thing anyone could drink.

EM: In your book, you mention that the first glass used for the Old-Fashioned was a goblet or wine glass. I’ve seen it served more often in a rocks glass. What’s your preference? And since it’s your mom’s favorite drink, which glass does she like?
RS: Yes, the old style Whiskey Cocktail was served “up” in a short-stemmed wine glass during the first half of the 19th century. Dedicated cocktail glasses as we now know them didn’t really exist back them. No one serves it that way anymore. I prefer an Old-Fashioned glass — a rocks glass–for an Old-Fashioned. They come in many styles and sizes — I have quite a few in my collection. But, somehow, an Old-Fashioned glass is always easily identifiably as an Old-Fashioned glass. The critical aspect is the glass’s heavy bottom, something that can withstand the muddling of the sugar cube, water and bitters, should you choose to make it that old-school way. As for my mom, she takes a Old-Fashioned glass as well. But she’s not too particular.

EM: You talk about something that really surprised me — that the drink was given to the Union Army, and even John Wilkes Booth was known to love the Old Fashioned, making it kind of a bad-ass cocktail. So how did this lovely, simple-genius drink get filled with so much fruit-cocktail nonsense?
RS: Yes, it’s kind of amusing the way the Whiskey Cocktail — as it would have been called during the Civil War — fed both sides of the conflict. Union generals drank them, too. And rather creepy that Booth liked them. But the Whiskey Cocktail was known at that time as a favorite of the young swells and dandies. And Booth was one of that group. How the fruit came about is hard to say. Fruit sometimes played a role in the drink prior to Prohibition, but as a garnish. After prohibition, the fruit sat within the drink, or was muddled. Some thing this came about during Prohibition to disguise the poor character of the booze used them. What we know for certain is that, in every cocktail book published after Prohibition, the recipe for an Old-Fashioned called for fruit, usually an orange slice and a cherry. The recipes stayed that way until the dawn of the 21st century, when mixologists began turning back to the recipe from the 1880s.

EM: I was also surprised by the bit of info you had saying the drink was kind of the world’s first DIY-esque drink, in which bartenders would give you a spoon and the bottle to pour. If you were in that situation, which whiskey would you pick, both foreign (out of NY, that is) and domestic (Empire State-centric)?
RS: “Foreign,” I would choose Elijah Craig 12YO, for a bourbon, or Rittenhouse 100, for a rye. Among New York state whiskeys, I’m waiting for New York Distilling Company‘s rye, which I believe will be released any week now.

Amy Zavatto

Amy Zavatto is the daughter of an old school Italian butcher who used to sell bay scallops alongside steaks, and is also the former Deputy Editor of Edible Brooklyn and Edible Manhattan. She holds her Level III Certification in Wine and Spirits from the WSET, and contributes to Imbibe, Whisky Advocate, SOMMJournal,, and others. She is the author of Forager's Cocktails: Botanical Mixology with Fresh, Natural Ingredients and The Architecture of the Cocktail. She's stomped around vineyards from the Finger Lakes to the Loire Valley and toured distilleries everywhere from Kentucky to Jalisco to the Highlands of Scotland. When not doing all those other things, Amy is the Director of the Long Island Merlot Alliance.

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