“I have heard of a forum, of phlegm-cutter and fog driver,..never in my life, though have lived a good many years, did I hear of ‘cock tail’ before. Is it peculiar to a part of this country? Or is it a late invention? Is the name expressive of the effect which the drink has on a particular part of the body?”

This precise inquiry in a 1806 New York newspaper called The Balance and Columbian Repository, was the first documented reference to any drink that involved mixing hard liquor with different spirits. If one were to scourge through the annals of history, it would be evident that the first form of a cocktail was a humble blend of water, sugar, whiskey, and bitters. 

This watered-down, pleasantly sweet alcoholic version of whiskeys or scotches became considerably popular in the bars and parlours across the United States. Gradually, demand for these “cocktails” spiked and customers began repeating their drink orders. But slowly, the practice of tweaking traditional hard liquor to make a slightly off-the-chart version of it became an enticing opportunity for bartenders across the nation. 

It was as late as the 19th century, when bartenders began embellishing their Whiskey Cocktails, a move that met with resistance from certain patrons. Purists and traditional drinkers had only recently embraced the whiskey cocktail wholeheartedly and were not inclined to explore additional variations. Thus, as a way to denote the OG “cocktail”, they would request bartenders to make them an “old fashioned” cocktail, referring to traditional whiskey cocktails.

Hence the Whiskey Cocktail evolved to be known as the Old Fashioned. 

In 1862, Jerry Thomas, a pioneer in the bartending realm, published Jerry Thomas' Bartenders Guide: How To Mix Drinks, featuring one of the earliest mentions of the term "Old-Fashioned." The book details the recipe for the Old Fashioned Holland Gin Cocktail, bearing similarities to the present-day version, including the use of the Old-Fashioned name. Notably, however, the recipe doesn't explicitly mention whiskey as the primary spirit, which has become a standard element in the modern interpretation.

The cocktail still has a contentious origin. It is often attributed to the Waldorf-Astoria in New York, with a connection to a private Kentucky club called Pendennis Club. In the Prohibition era, the classic Old-Fashioned transformed, adopting a more complex profile with muddled orange and cherry. The shift sparked debates—some claim it concealed the inferior taste of Prohibition whiskey, while others suggest confusion with fruit-centric cocktails.

The fruit-infused rendition of this classic cocktail dominated the mid-20th century. However, it faced a decline in popularity among younger drinkers who favoured disco-era beverages of the 1970s and 80s. Despite its seemingly outdated name, the Old-Fashioned endured through the turn of the millennium. As a testament to its timeless charm, Louisville declared the Old Fashioned its official cocktail in 2015, commemorating the drink with an annual two-week celebration called the Old Fashioned Fortnight every June.