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How to Make a Fancy Free, an Outstanding Old Fashioned Made With Maraschino

For when you're feeling footloose.

fancy free cocktail old fashioned glass orange peel garnish Getty Images

“But I might see young Cupid’s fiery shaft
Quench’d in the chaste beams of the watery moon,
And the imperial votaress passed on,
In maiden meditation, fancy-free.”
A Midsummer Night’s Dream, Act II Scene I

You might think Fancy Free is a silly name for a cocktail, but given where it comes from, we should be thankful it’s not called “Single and Ready to Mingle.”

To explain: “Fancy free,” used to be a popular phrase, but it has all but disappeared. I realize it sounds like a grocery store rewards program or a sugarless cat food or something, but the phrase was coined by none other than Shakespeare himself and essentially means “single and carefree.” It first appears in the admittedly indecipherable passage up top, which, translated to workable English, describes how Cupid aimed his arrow at a young lady but the moon made him miss, so the lady continued on free from the encumbrances of love that getting hit with Cupid’s arrow would bring— she still didn’t fancy (read: have a crush on) anyone, so was “fancy free.” Think of it as the Elizabethan DTF.

Now, what does any of that have to do with whiskey, maraschino liqueur and bitters? Not only do I not know, but I suspect no one knows. Crosby Gaige, from whose 1940 book Cocktail Guide and Ladies Companion this drink comes, was not a bartender, just a recipe collector and preferred cocktails with eccentric names—so much so that if one of the cocktails he collected didn’t have an flamboyant name, he went ahead and gave it one. “It may be that [cocktails] are now and then entitled to new and different names,” he asserts in his introduction, “I have indulged myself somewhat with this notion in the present work.” This might explain the Psychopathia Sexualis (gin, vermouth, sherry and bitters), the Why Minks Make Love (apricot brandy and lemon) and the Widows are Seldom Destitute (Dubonnet, vermouth and bitters). He’s also the one who changed the Atty cocktail to the Arsenic & Old Lace for seemingly no reason at all and in the present case took the Improved Whiskey Cocktail—an established classic for 60 years by that point—dropped the absinthe and called it the Fancy Free.

At least Fancy Free is fun to say. His “Mrs. Solomon Wears Slacks” (brandy, curacao and bitters) was never destined for stardom, no matter how good it might be. And it’s a good thing too, because the Fancy Free is a wonderful little Old Fashioned variation and among the most-deployed and -enjoyed “dealers choice” whiskey cocktails in a craft bartender’s arsenal. The Fancy Free is an Improved Whiskey Cocktail (whiskey, maraschino, bitters and absinthe) without the absinthe. Simple as the substitution is, it’s a liquid argument for the idea that subtle changes mean everything—where the Improved Cocktail is dominated by the anise and licorice of absinthe, the Fancy Free allows the maraschino’s floral, earthy nuance to express itself across every part of the tasting experience. In other words, where the Improved Cocktail is encumbered by absinthe, the Fancy Free is, yes, fancy free.

Fancy Free

Build in an Old Fashioned glass over the biggest piece of ice you have. Stir 10 to 15 seconds and garnish with an orange peel.


Whiskey: Pretty much everyone says to use bourbon in this and that’s certainly the way I’ve always made it. In the experiments for this article, though, I was surprised that my favorite version was with the mild and overlooked Canadian Whiskey. Gaige himself called for Fine Arts Whiskey which no longer exists, but which would’ve been a milder five-year old blend put out by the Canada Dry company and presumably with more in common with Canadian whiskey than bourbon. 

History notwithstanding—side by side, I thought that Canadian whiskey was a more composed final product, allowing the maraschino to speak without the two stepping on each other’s toes. Crown Royal or Canadian Club are both good, as are others. If using bourbon, grab a milder kind—now is a good time to use one of the softer wheated bourbons like Maker’s Mark, or a solid 80 proof option like Four Roses Yellow Label.

Final note on whiskey: If you use something lower than say 86 proof, you’ll want to use a little less liqueur to prevent it from getting too sweet. And if it does end up too sweet, just add a 1/4oz more whiskey until it comes back into balance.

Maraschino: Maraschino liqueur is a liqueur made from the sour marasca cherry, which grows most readily around the Adriatic Sea in Italy and Croatia. It’s different from something like Cherry Heering in that it is distilled from cherries as opposed to infused with them, so it has cherry notes, sure, but also earthy and funky notes as well. The vast majority of bars who stock one stock the annoyingly tall Luxardo bottle, which works great. If you happen to live near a specialty liquor store that sells the Maraska brand, this would be the cocktail to try it in, more cherry flesh than the Luxardo’s cherry pits, richer and brighter.

Orange Bitters: This is an earnestly hard question. As far as I’m concerned, there still isn’t any one single brand of orange bitters that rises to the top. Many excellent bars make bitters blends of equal parts Fee Brothers and Regan’s orange bitters (a.k.a. “Feegans”). Some more add a third part of Angostura Orange into that blend, which has a pronounced zestiness that some people love and others find synthetic. My own orange bitters blend has swelled to 6 brands, is so byzantine it would embarrass me to print and is only for people who have been frustrated to the point of madness about the lack of good orange bitters out there.

All of this is to say: Whatever orange bitters you get is fine. Which isn’t really true, but it’s true enough. If you’re feeling plucky and want to order off the internet my favorite all-purposers are probably the juicy and spice-heavy Miracle Mile, and the lovely, floral Bitter Queens.

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