Some cocktails have a story, some don't, and some seem like they don't only because no one's paying attention. The Fancy Free is like all of those. It is a classic, a fairly well known classic, but there's not much history to it, or, more accurately, the history is sort of not about the drink at all. Instead, the Fancy Free is about the choice of whiskey.
The Fancy Free is documented in the remarkable volume, Crosby Gaige's Cocktail Guide and Ladies' Companion, first published in 1941. In total, the book is a collection of humorous essays published, as claimed on the title page, "...for Hussies and Homebodies." Safe to say that, unlike other books of its time, Gaige's guide was for the home cocktail enthusiast, and not a reference for professionals.
It shows. Gaige's recipes are inconsistent at best, and a mess at worst. Measurements are confusing in some places, baffling in others, and one gets the impression that the author's idea of a jigger as a unit of volume is strictly defined by whatever vessel was at hand, then ignored half way through the ingredient list, however, Gaige can be forgiven. He wasn't a bartender, he was a theatrical producer on Broadway with a taste for high society and elegant cocktail lounges who often wrote on the topics of both food and drink. Less intriguing is the insistence on shaking everything, but most books of the day call for shaking as if the concept of stirring a cocktail was as alien to the bartenders of the time as was Summer clothing to the Victorians. We are, however, able to parse some sense from Gaige, and the Fancy Free is one drink we can address directly.
It's easy to define the Fancy Free as an Old Fashioned with maraschino liqueur. Modern recipes do call for the same ingredients, whiskey, maraschino, and bitters, but the drink itself is more likely an adaptation of the Improved Whiskey Cocktail. In the 1800s, a wave of "improved" cocktails made the rounds, not as an evolution of the Old Fashioned, but as an alternative to what was then known only as a Cocktail. It was about this time that the term old fashioned came into use because patrons, wanting a traditional cocktail instead of an improved one, would order a cocktail made in the old fashioned way.
One can also see the Fancy Free as a style of Manhattan, but maybe only in the fact that the Fancy Free, like the Manhattan, is served up. Sure, you can find plenty of Fancy Free recipes that do specify a rocks glass and ice as a nod to the cocktail's roots, but Gaige not only served it up, he served it in a sugar rimmed cocktail glass.
The sugar was necessary as Gaige only used 2 dashes of maraschino liqueur, which, on its own, isn't enough to add balance. Modern recipes up the liqueur to half an ounce, as do we, thus rendering the sugar redundant. The whiskey, however, requires some careful consideration. Gaige specifies Fine Arts Whiskey, a brand of whiskey no longer available, so what do we use instead?
Fine Arts Whiskey is, or was, a blended whiskey produced and distributed by Canada Dry Ginger Ale, Inc, of New York City. Given the history of Canada Dry, this makes sense, although they haven't distributed liquor in many years, and were never really committed to the market except for a brief time during the 1930s and 1940s, the very time of Gaige and his light hearted book.
Originally, Canada Dry was a Canadian company. They found success after shipping their ginger ale to New York in the 1920s where it was embraced as a cocktail mixer. After the repeal of Prohibition, it was natural for the company to set up shop in New York, and capitalize on their renown by distributing whiskey. Their brand was Fine Arts Whiskey, a blend of 5 whiskeys, all aged 5 years for a smooth sip every time, or something to that effect. Details in advertising were scarce in early 20th century America, but one can deduce, or assume, that Fine Arts Whiskey was a blended Canadian whiskey, similar in construction, if maybe not in taste, to brands like Canadian Club.
Canadian whiskey would also have been fashionable in New York at the time, as confirmed by other drink references calling for specific brands of Canadian whiskey. This, too, makes sense because Canadian whiskey isn't bourbon, and would have been known as rye whiskey, even if it doesn't exactly taste like contemporary examples of straight rye. It doesn't taste like bourbon, either. Bourbon, especially wheated bourbon, can be sweet on the palate, and that's not good for a Fancy Free, especially in modern proportions. Bourbon makes the cocktail too sweet, and, although modern recipes almost universally call for bourbon, they are all hard to balance against the volume of liqueur.
Maraschino liqueur is as unforgiving as a stick of dynamite with a lit fuse. One drop excess in a drink is enough to ruin it. Maraschino is sweet, and powerfully flavored in a polarizing way. Matching it with bourbon is a challenge, and many face this challenge by adding more bourbon. That's really more of a hack, and avoids the issue of balance. Rather than adding more bourbon, lower the amount of liqueur. Gaige only used 2 dashes, and he was using Canadian whiskey. Knowing this, and considering the nature of Canadian whiskey, and knowing we want more than a few dashes of liqueur, thinking of the Fancy Free as a variation, not on an Old Fashioned, but on a Manhattan starts to make sense. Why not try a straight rye whiskey, or, better yet, an overproof rye with enough fortitude to tame the maraschino liqueur.
Suddenly this cocktail works. Using rye, James Oliver Rye to be exact, brings everything in line and the Fancy Free suddenly goes from being a good drink to being a great one. The rye, however, has to be spicy, assertive, relatively dry and boozey, otherwise you face the dynamite problem again and the liqueur is still a sugar bomb with an aroma that smells like Grandma's parlor. Stick true to spec here and you will be rewarded, but, for all of Gaige's charm and wit, please do avoid the sugar rim. This is a stout drink with a complexity to match. Leave the rim as it is and don't pretend it's candy.
Stir with ice and serve up. No garnish.
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