The Simple Swap That Turns An Old Fashioned Into A Fancy Free Cocktail

If someone tells you that you're drinking an "improved" cocktail, it could be a fancy free. The latter name for the drink first appears in print in Crosby Gaige's "Cocktail Guide and Ladies' Companion" from 1941. The fancy free is built on the foundation of the old fashioned, an unpretentious combination of whiskey, bitters, sugar, and water that was once known simply as the whiskey cocktail. In fact, it was one of the first cocktails – though the Sazerac is often considered the very first. To "improve" the drink and turn it into a fancy free, a dash of maraschino, a nutty, bittersweet liqueur made from cherries, is added. In a nutshell, the drink mixes bourbon or whiskey with maraschino liqueur, orange and Angostura bitters, with some ice — topped with a citrus peel for garnish.

Why maraschino? During the 20th century, European liqueurs were all the rage in the United States. As cocktail culture evolved, bartenders started taking liberties with basic recipes in order to seduce their guests with new and different flavors. Before the fancy free was a glimmer in a bartender's eye, the improved whiskey cocktail appeared in Jerry Thomas's 1876 edition of "The Bar-tender's Guide; or How To Mix All Kinds of Plain and Fancy Drinks." The improved version included maraschino, as well as a dash of absinthe, which was hugely popular at the time. By removing the absinthe from its ingredients, the fancy free eschews the licorice element and focuses on the bitter cherry character.

In the modern cocktail era, as enterprising bartenders tinker with recipes, they have found more ways to reinvent the old fashioned. In 2006, Little Branch bartenders Richard Boccato and Michael McIlroy concocted the American trilogy. This riff blends equal amounts of apple brandy and rye, then swaps out the Angostura for orange bitters. 

Another inventive twist that has gone on to become something of a modern classic is the Oaxaca old fashioned created by Phil Ward in 2007. Here, tequila steps in for whiskey, with mezcal adding an extra kick. Ward finishes the drink with agave syrup instead of sugar and dresses it up with a flamed orange peel. That same year, Don Lee at PDT in New York used a technique called fat-washing to infuse bourbon with bacon; he swapped the sugar for maple syrup to create the Benton's old fashioned.  

Since then, bartenders have fat-washed with everything from peanut butter to coconut oil; standard sugar or simple syrup have been replaced by agave, maple syrup, flavored syrups, and liqueurs. Even a simple swap of bitters can transform a whiskey cocktail with a new flavor profile featuring chocolate, cherry, walnut. All this goes to show that while the old fashioned might be considered, well, old fashioned, it's just as relevant today as it was when it arrived on the cocktail scene.