I wrote this piece for the cityhomeCOLLECTIVE blog last year for their “Cocktails 101” series. See more delicious photos from the party, as shot by Tristan Shepherd, here. Edited by the lovely and talented Amy Tibbals.

It only takes one sucky Old-Fashioned to put you off this drink for life. My first introduction to the Old-Fashioned was the one served for pretty much every holiday gathering with my family. It looked like fruit vomit, and tasted like booze-tinted water. My-relative-who-shall-remain-nameless [he meant well, really] smashed great masses of fruit—orange slices, godawful red maraschino cherries, sometimes some lemon—in the bottom of a glass, stirred in a spoonful of sugar, a spoonful of grenadine, and a dash of Angostura bitters. Then he filled the glass with ice, added a splash of Canadian Club, and quite a few glugs of club soda [ladies, after all, shouldn’t be served full-strength cocktails. Psh.]. I’d smile weakly and say thank you, and then later my brother-in-law and I would scrounge for the bottle of bourbon I gave them the year before at Christmas and make our own drinks. Booze: the gift that keeps on giving.

In defense of my relatives, the aforementioned version of this wayward drink is the one that most post-Prohibition-era Americans drank, and expected to be served if they ordered one at the club. And until Don Draper’s character made it sexy again on Mad Men, nobody without an AARP card would be caught dead ordering one at a hipster bar. It’s the version I’d been taught to make at my first bar gig in the 1990s. And it’s a goddamn shame, too, because in its purest form, the Old-Fashioned is a tasty thing of beauty: just a bit of citrus, sugar, bitters, a large cube of ice, and booze. Barmen in the late 1800s started making drinks by request “the old-fashioned way” in protest against what their patrons saw as unnecessarily elaborate cocktail chicanery of fruit concoctions, fussy garnishing, and flashy shaker work. Ironically, that original Old-Fashioned recipe was hijacked after Prohibition and turned into just the sort of muddled-fruity-watery vulgarity that the 1880s bartenders had been protesting. Cocktail history, my friends, is a fickle bitch.

Flash forward to now, people, and keep up, ‘cause this is where it’s going to get tricky. In today’s bourbon-is-sexy-again cocktail-crazed scene, you never know what you’re going to get if you order an Old-Fashioned. You may get a stunning—and short [I’m not gonna lie, 2 oz. of liquid looks pretty puny with only a big ‘ole ice cube keeping company]—Old-Fashioned at a place like Bar X, or as mixed up by the booze slingists of C&S Spirits. They’ll kill it, you’ll love it. Or, you could end up with my in-laws’ version at the golf club. Sucks to be you.

*Solution: start making your own. Try a few out and find what you like. Here’s a few basics to get you get started:

THE BOOZE: It doesn’t have to be the most expensive bottle on your shelf. Bourbon? Classic. Rye whiskey? A nice touch, and historically accurate. Southern Comfort? Um, not what I’d pick, but okay for a 21-yr-old frat boy. Brandy? Way sweet, but it’ll work in a pinch. Tequila? WTF, people. No more experimenting. Bottom line, I prefer a 90 proof or higher bourbon or rye for making Old-Fashioneds; make the booze the star.

THE BITTERS: You can get super ambitious and make your own artisanal bitters, and in a couple of months, if they turn out, you’ll be ready to make a drink. You can buy fancy-schmancy fruit bitters, like Fee Brothers, online, but Angostura bitters are available at most supermarkets and are a classic addition.

THE SWEET: Use white sugar, Demerara or turbinado sugar, hand-harvested by virgins, organic beet sugar, sugar shaved raw from a pressed loaf smuggled through customs from your last Cuban vacation. Sure, why the hell not. Stay away from brown sugars.  

THE FRUIT: Please, for love of all that’s holy, try to keep the fruity additions to a minimum, and make them the background notes to support the flavor of your liquor. Avoid a fruit salad that you have to slurp around to get to your drink.

THE WATER: If there’s one thing you remember when making this drink, it’s to watch your water content; a mere baby splash of club soda or water [less than ½ oz.] will open up the nose of your booze nicely, but a watery Old-Fashioned is just fuckin’ gross. If you’re pulling your rocks from an ice bucket, make sure that they’re cold and hard..not floating sadly in water. Oh, and the bigger your cube, the better. Now, let’s make drinks, shall we?

The Classic Old-Fashioned [by booze historian David Wondrich for Esquire]

Place ½ tsp of loose sugar in the bottom of an Old-Fashioned glass, then add two or three healthy dashes of Angostura bitters and ½ tsp of water. Muddle until the sugar is dissolved. Add three ice cubes to the glass. Stir. Add 2 oz straight rye or bourbon whiskey. Stir again. Twist a thin-cut swatch of lemon or orange peel over the top, add a stirring implement, and let sit for one minute. After that, enjoy thoroughly.

 

Cranberry-Clementine Old-Fashioned [a cross ‘twixt the 1880s classic and a mid-century cocktail, with a sparkly rim for festivities’ sake. I made a cranberry-rum citrus jam to use as the sweetening/fruit element, but you can totally use leftover, cold, cranberry sauce from your holiday dinner and it’ll rock, just the same.]

Rub ½ of the rim of a lowball glass with ¼ of a Clementine wedge; dip the citrus-coated rim of the glass in turbinado sugar to coat. Then, to a short glass add: juice of ¼ Clementine wedge [drop it into the glass, if you want to be like Don Draper’s daughter], three dashes bitters, ½ tsp. cranberry jam [or cranberry sauce], ½ tsp sugar. Stir with a spoon until sugar dissolves. Add 2 oz. bourbon and 3 to 4 cubes of ice, then top with an optional tiny-baby splash of club soda. Stir gently to combine, garnish with 2-3 sugared cranberries, and enter the gates of heaven.