I took a seat at the corner of the L-shaped bar at Analogue, a new watering hole that opened last December in the Chicago neighborhood of Logan Square—an area that is swiftly becoming to the Windy City what the East Village is to New York. That is, chockablock with cocktail options.

I was already a few sips into my selection when I noticed an item at the bottom of the menu that had escaped my attention: “Shot of the Day: Old-Fashioned.”

The Old-Fashioned, as a shot? The tariff was only $5. What could I lose? My companion and I ordered up two of the oddities and the bartender soon arrived with three shots of bourbon (in the spirit of good fellowship, he had decided to join us). On top of each was a triangular orange wedge, which, I was told, had been soaked in Angostura bitters. Nearby was a salt shaker filled with sugar. Following the instructions given, I shook a bit of sugar onto the side of my hand, licked it off, threw back the shot and then bit into the orange. It was an Old-Fashioned by way of the tequila ritual practiced nightly at bars across the world, and it was delicious.

Since roughly the turn of the current decade, the Old-Fashioned, a drink nearly as old as the republic (if you count its pre-1880s life as the Whiskey Cocktail—and I do) has enjoyed a heyday such as it has not seen since the hard-drinking 1950s.

Not only do today’s mixologists know how to make an Old-Fashioned properly—that is, in its elemental, pre-Prohibition, non-muddled-fruit form—but they have lovingly riffed on it the way jazz musicians draw on the Great American Songbook, creating a host of modern classics such as the Oaxaca Old-Fashioned (Phil Ward’s work), Honey-Nut Old Fashioned (Marcos Tello) and Benton’s Old Fashioned (Don Lee). All of the above creations I included in my recent ode to the drink, its history and its modern incarnations, The Old-Fashioned: The World’s First Classic Cocktail.

I first began to notice that the Old-Fashioned was enjoying renewed respect and popularity in 2009 or thereabout. Just as they had with other drinks from the classical canon, mixologists had finally gotten to the bottom of how the cocktail had once been made—the formula that had earned it a reputation of one of the cornerstones of the bartender’s art. Out went all the bad post-Prohibition habits that had clung stubbornly to the drink—the muddled fruit, the spurt of soda water, the neon-red maraschino cherry, the cheap whiskey and even cheaper ice. In its renewed form—whiskey, sugar, bitters, water—it matched the classical definition of the cocktail. Bars began to wear it as a badge of honor, placing it high on the cocktail list. Customers responded, ordering it in numbers—and then ordering it again because, lo and behold, this new Old-Fashioned actually tasted good.

Brawny Chicago, only three hundred miles from Louisville, liked its Kentucky bourbon, and it takes a very small leap of logic to imagine that they frequently liked their whiskey in the form of an Old Fashioned. An 1870 Tribune survey of the drinking scene identified the Whiskey Cocktail as a popular local quaff, while an 1898 story in the New York World told how, when women at the Waldorf-Astoria Hotel slyly asked for “tea in the Chicago style,” they got a cupful of Whiskey Cocktail.

Not satisfied with that, however, those same cocktail bars and bartenders began to roll out their personal iterations of the drink. They are still doing so today.

On that same Chicago trip where I uncovered Analogue’s Old-Fashioned Shot, I visited Bub City, a barbecue joint where esteemed barman Paul McGee is in charge of the liquor program. Among the many bottles of bourbon on the back bar is the sort of dispenser typically associated with Jägermeister shots. Only McGee had filled the bottle perched atop his machine with Very Old Barton bourbon, demerara syrup, mole bitters and water to create the bar’s very own Old-Fashioned dispenser.

Even further into the realm of the unexpected, Chicago is also the home of my favorite deconstruction of the cocktail: In the Rock, a classic creation at The Aviary, Grant Achatz’s laboratory-cum-bar. As the name might suggest, Aviary injects all the ingredients one associates with the Old-Fashioned into a hollow ice egg. It’s then served in a rocks glass and cracked by a sort of custom-built slingshot device, which releases the drink’s golden core into the vessel. (Charles Joly, who took charge of the bar program in 2012, currently fills those chilly orbs with the makings of a Remember the Maine.)

I guess I ought to expect such Old-Fashioned invention from the Second City, though. No one knows (or will likely ever know) where the first Old-Fashioned was served, but much of my research into the drink pointed to the possibility that Chicago was one of the first cities to embrace it. The first-known appearance of a recipe for an Old-Fashioned came in an 1888 cocktail book written by Theodore Proulx, a Chicago-based barman who had worked at Chapin & Gore, a famed Chi-town drinking hall of the late 19th century.

Brawny Chicago, only 300 miles from Louisville, liked its Kentucky bourbon, and it takes a very small leap of logic to imagine that they frequently liked their whiskey in the form of an Old-Fashioned. An 1870 Tribune survey of the drinking scene identified the Whiskey Cocktail as a popular local quaff, and an 1898 story in the New York World told how, when women at the Waldorf-Astoria Hotel slyly asked for “tea in the Chicago style,” they got a cupful of Whiskey Cocktail.

And when, in 1893, Chicago hosted the first meeting of the newly formed International Association of Bartenders, the proper way to build an Old-Fashioned was hashed out the very first day. The town had its priorities.

San Francisco, meanwhile, does not have as robust a historical record for Old-Fashioned thirst. Pisco Sours and Pisco Punch were more beloved. But that was then; this is now. As New York has adopted some of San Francisco’s drinking habits (Negronis, Fernet, etc.), San Francisco has returned the favor, going in for brown and boozy cocktails far more than it had in the recent past. The embrace of the Old-Fashioned is part of that change.

In April, I wandered down to the city’s waterfront, where Erik Adkins has assembled a daunted collection of rare and extinct American whiskeys for Hard Water, a well-lubricated new restaurant with Southern-style cuisine. Every Old Forester Birthday Bourbon since 2002? They’ve got it. The super-expensive A.H. Hirsch 16-year-old? Yes. Plus, of course, many other humbler offerings.

The next day I met Adkins. He told me that an Old-Fashioned can be made from almost any whiskey in their collection. If only I’d known.

“Brown and boozy is on the rise,” observed Adkins in an email. “I think that Seattle and New York are rubbing off on us.” According to Adkins, at the Slanted Door the Whiskey Cocktail (aka Old-Fashioned) is one of the most popular drinks on the menu. And at Hard Water he now features The Dixie Cocktail, a variation on the Old-Fashioned from Tom Bullocks’ 1919 The Ideal Bartender. “The Whiskey Cocktail is a great way to explore the subtle and sometimes not-so-subtle differences that American whiskies share.”

The next night, I stepped up to the bar at Tosca Café, the ancient North Beach landmark that was recently given a new lease on life by chef April Bloomfield and restaurateur Ken Friedman. Everything on the cocktail menu looked good, but the Old Grampian, with its unusual mix of two scotches—the meaty blended Blank Note and the high-end Islay single malt Lagavulin 12-year-old—caught my fancy first. I had chosen wisely. It was rich, full-bodied and complex, with a touch of honey for sweetness and two kinds of bitters. I complimented the bartender.

“Yeah,” he said. “It’s an Old-Fashioned, basically.”

The Classic Old-Fashioned Nearly stomped out of existence by its fruity mid-20th-century counterpart, the true Old-Fashioned is as traditional as they come. More Recipes →

The Riff Old Grampian Rich, full-bodied and complex with a touch of honey for sweetness and two kinds of bitters, the Old Grampian is cocktail that evolves in the glass. More Recipes →

Photo originally published in The Old-Fashioned by Robert Simonson, copyright © 2014. Photo by Daniel Krieger © 2014. Published by Ten Speed Press, a division of Random House, Inc.