I once found myself in a saloon in the windswept badlands of northern Nevada. As I sipped whiskey beside a crew of grizzled miners, a purty little desert rose sitting alone caught my eye. “I’ll buy the lady a round,” I told the barkeep, an old man with long gray hair and a weathered Hell’s Angels cut. “What’s your finest Chardonnay by the glass?” He fixed me with a stare as harsh as a dust squall.
“Son, around here it’s beer or whiskey.”
“Well, alright. Make it an Old-Fashioned—extra sweet.”
He lumbered to the backbar and dumped bourbon, bitters, and a mountainous heap of sugar into a shaker. Moments later came the sharp clack of boots on wooden planks. The young woman stopped beside my stool. She slowly emptied her glass onto my loafers. The miners howled with savage laughter. “You tryna give me cavities, city boy?”
The evening did not go my way, but I left that dusty bar determined to understand the nuances of a proper Old-Fashioned. Back in New York City, I paid a visit to Anthony “the Professor” Baker, the celebrated bartender at Warren Street Restaurant & Bar, to learn the history of this most classic of cocktails—along with a few insider tips and recipes.
Whence the Old-Fashioned?
The origins of the Old-Fashioned are anything but glamorous, Anthony explained. Early American whiskey was cheap and rough—the sort of spirit better suited to cleaning tile than sipping. 19th-century bartenders softened the harshness by adding sugar, bitters, and a twist of citrus.
As bartenders began concocting increasingly elaborate drinks in the 1860s, traditionalists pushed back, asking for their whiskey “the old-fashioned way.” The name stuck. For Anthony, the Old-Fashioned is a bridge between cocktail and straight pour. “Order it when you’re not quite ready for whiskey neat, but you’re finished with richer whiskey cocktails like sours,” he said.
Fortunately, American whiskey has come a long way from the rattlesnake juice that passed for liquor in the Antebellum era. Where early Old-Fashioneds demanded a heavy hand with sweetener, the modern version calls for restraint. Anthony recommended using no more than a quarter ounce of sugar, honey, or demerara—just enough to lift the bourbon’s flavor without burying it.
What You Need at Home
A few simple tools in your bar cart make a big difference, Anthony told me. Skip the guesswork and use a jigger to measure out pours. Invest in a high-quality ice mold for large, slow-melting cubes. A sturdy mixing glass and bar spoon are non-negotiables.
“Keep it simple for classic Old-Fashioneds,” Anthony insisted. “Whiskey, bitters, and a touch of sweetener. That’s it.” Skip the muddled fruit. Use one large cube of ice and a fresh orange peel as a garnish. A candied cherry, only if you must. And for the love of Jesus, Mary, and Sainted Joseph the good and kind Carpenter, go easy on the sugar.
Below, Anthony’s classic build and a couple of playful riffs.
Classic Old-Fashioned
A version as classic as Caddyshack. It’s so damn tasty, I can never stop at just one when I dine at Warren Street Bar & Restaurant. Anthony sources crystalline ice cubes the size of Rubik’s Cubes from a well-known New York purveyor, but a silicone mold in your home freezer works just fine.
Ingredients
- 2 dashes Angostura Aromatic Bitters
- 2 dashes Regan’s Orange Bitters
- 0.25 oz Demerara syrup
- 2.25 oz bourbon or rye whiskey
Instructions
- Add all ingredients to a mixing glass.
- Fill with ice and stir with a bar spoon for about 10 seconds.
- Strain into a rocks glass over a large ice cube.
- Rub the glass’s rim with a fresh orange twist and use it as a garnish.
Nutty & Old-Fashioned
This take requires sturdier mixology chops, but it’s still feasible to make at home. “The Nutty & Old-Fashioned keeps the bones of the classic, but layers in toasted walnut warmth,” Anthony said. “Macerate walnuts in the rye, and add a touch of banana to soften any harsh bitterness. The finish should be round and deep.”
Ingredients
- 2 dashes banana bitters
- 2 dashes Smoke & Oak bitters
- 2 dashes Angostura Aromatic Bitters
- 0.25 oz maple syrup
- 2.25 oz toasted-walnut-infused rye whiskey
Instructions
- Add all ingredients to a mixing glass.
- Fill with ice and stir with a bar spoon for about 10 seconds.
- Strain into a rocks glass over a large ice cube.
- Garnish with a candied pecan.
Mexican Old-Fashioned
“Say, amigo, you know how to make a Mexican Old-Fashioned?” That’s the opening line of my future Western.
This version is complex and luscious. “It’s delightfully layered—vanilla from the reposado, smoke from the mezcal, chocolate richness, and a quiet spark of heat,” Anthony told me. “It’s a crowd-pleaser—and after one sip, you’ll understand why.”
Ingredients
- 2 dashes chocolate bitters
- 3 drops chili tincture
- 5 drops saline solution
- 0.25 oz raw agave syrup
- 0.25 oz mezcal
- 2 oz reposado tequila
Instructions
- Add all ingredients to a mixing glass.
- Fill with ice and stir with a bar spoon for about 10 seconds.
- Strain into a rocks glass over a large ice cube.
- Garnish with a sage leaf.
