All photos by Liz Barclay (@liz_barclay)

In 1890, the New York Sun printed a small item about the “latest drink of the habitués of Madison Square.” The trendy cocktail was something called the Old-Fashioned, which the newspaper described as “very soothing and graceful to the palate.”

This little wonder of a libation wasn’t actually very new at all. It was just the good old Whiskey Cocktail—that is, whiskey, bitters, sugar, water, and a twist—reclaimed by its devotees and shed of all the liqueurs and other frippery that over-inventive bartenders had been throwing at it. Thus returned to its pristine form, folks began to call it the Old-Fashioned Whiskey Cocktail, and, in time, just the Old-Fashioned.

Truth be told, New York was a little late to the party on this particular fad. Chicago papers had been full of mentions of the popular tipple for nearly a decade before the Sun got around to it. In fact, the first cocktail book to include a recipe for the drink, published in 1888, was written by Chicago barman Theodore Proulx.

Finding a properly wrought Old-Fashioned isn’t nearly as hard as it was just five years ago.

But that’s not to say that New Yorkers were wanting for a decent Old-Fashioned. Col. Jim Gray, a waistcoated braggart who manned the bar at the famed Fifth Avenue Hotel for 30 years beginning in 1880, was particularly renowned for his way with the cocktail. (The Colonel also claimed he invented the drink, but it’s likely no one but the Colonel himself believed that boast.)

Whatever the prospect may have been for 19th-century Old-Fashioned lovers, they are decidedly bountiful for their modern counterparts. Thanks to the ever-expanding knowledge and reach of the bartender community, finding a properly wrought Old-Fashioned isn’t nearly as hard as it was just five years ago. Still, some bars do it better than others. In my research for The Old-Fashioned, my new book-length study of the iconic drink, I uncovered many of the five boroughs’ finest renditions of the cocktail. Here are the standard-bearers you ought to know. Tell them the Colonel sent you.

Robert Simonson writes about bars, spirits, and cocktails for The New York Times. His book, The Old-Fashioned: The Story of the World’s First Classic Cocktail, is now available from Ten Speed Press.

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