As a true whiskey enthusiast, you know there is nothing better than sipping on perfectly crafted whiskey cocktails. But have you ever taken a moment to ponder the origin stories behind these beloved drinks? Today we’re diving into the history of four of the most iconic whiskey cocktails, exploring their origins and the colorful characters who brought them to life. Like many tales from whiskey’s formative years, mystery shrouds some of the finer details, but researching these cocktails reminds us that there is no shortage of wild tales to fill in the gaps!

Manhattan: The decisive origins of the Manhattan cocktail are lost to history. Several accounts unsurprisingly pinpoint late-1800’s Manhattan as the birthplace of this classic cocktail, but one small-town Wisconsin newspaper has a more intriguing spin. In March of 1899, the Racine Daily Journal published an article explaining that New Orleans native Colonel Joe Walker invented the Manhattan during a yachting trip on which, “by some oversight, the liquid refreshments in the icebox were confined to Italian vermouth and plain whisky.” The Colonel mixed the two, liked the results, and tinkered with it upon returning to dry land. He christened his final recipe “The Manhattan” in honor of his friends on New York’s famed island, and the rest, according to the Racine Daily Journal, is history. The paper ends the piece by drawing a sharp contrast between French and Italian vermouth, closing with a fabulously stern admonition. “A cocktail made from the French brand is no more a Manhattan cocktail than it is a Spanish omelet."

Rob Roy: A variant of the Manhattan whiskey cocktail, a Rob Roy is made with Scotch instead of bourbon. Unlike its close relation, the Rob Roy has a well-established origin story involving the Scottish Robin Hood. Highland clan chief Rob Roy MacGregor became a living legend in 18th century Scotland because of his reputation for stealing from the rich and giving to the poor. His legacy continued to grow after his death, and his story was recounted by Sir Walter Scott (1817), William Wordsworth (1803), and Walt Disney Productions (1953). Liam Neeson played Roy in a 1995 film shot entirely in the Scottish Highlands. The “Rob Roy” cocktail was born in the late 1800s when a clever bartender at New York’s Waldorf Astoria created the drink to publicize a new operetta based on the folk hero’s life. Having invented a classic whiskey cocktail now enjoyed the world over, we hope he got a good tip that night!  

Old Fashioned: As bartenders started experimenting with absinthe, syrups, and fruit juices in the 1850s, the American cocktail scene was beginning to have a moment. But even in these early days, there were those that longed for simpler times. Eschewing the accoutrement of the trendier cocktails, these nostalgic whiskey drinkers popularized a simpler cocktail that elevated the taste of the spirit itself. The exact origin of the Old Fashioned is unknown, but because whiskey enthusiasts abhor a vacuum, theories abound.

According to one legend, a bartender at the Pendennis Club in Louisville, Kentucky created the whiskey cocktails by muddling sugar with bitters, adding a splash of water, and then adding whiskey and ice. Some experts offer alternative origin stories, but they all agree that the Old Fashioned maintains its reputation as one of the finest options available for a whiskey-forward (usually bourbon or rye) cocktail that even the most traditional drinker can enjoy. Cole Porter takes it further in his classic song “Make It Another Old Fashioned Please,” asking to leave out the bitters, orange, and cherries (leaving whiskey as the only remaining ingredient). Now that’s as old fashioned as it gets!

Whiskey Sour: Although the first published recipe for a whiskey sour appeared in Jerry Thomas’s 1862 book The Bartenders Guide, history buffs confirm that the drink had been around for ages by the mid-nineteenth century. Necessity, as they say, is the mother of invention, and sailors on the high seas had little in the way of mixers as they circumnavigated the globe on wooden vessels. What they did have were crates full of lemons and limes, loaded on board to stave off the swollen gums and severe joint pain caused by the often-fatal disease scurvy. Committed to a healthy intake of vitamin C and passionate about strong drinks, these sailors mixed their citrus with whiskey and lived to see another day. Later, fans of the early whiskey sour added sugar and various garnishes to elevate the flavor and aesthetic, but the heart of this lifesaving cocktail remains unchanged to this day.

Nothing elevates a cocktail like using whiskey from your very own barrel. At Barrel Global, our goal is to make that a reality for whiskey lovers who are ready to take their hobby to the next level. We’re on a mission to make whiskey barrel ownership accessible to collectors worldwide. As the first ever global marketplace for whiskey barrels, you can connect with distilleries and collectors around the world to build your own portfolio. For a whiskey experience unlike any other, request access today.

‍