Let Those 'I-Don't-Care' Days Begin With a Fancy Free

There are two key signifiers that cement the fact that I am, officially, unambiguously, and regrettably, an adult. It isn’t my age (which, depending on the day and who you’re asking, is anywhere from 27 to 50 years old), and it isn’t the horizontal lines deepening on my forehead from the countless times people, life, etc. have elicited a brow-raising “Are You Fucking Kidding Me?” expression from my face. I’m not even a home-owner! I’ve never kept more than $20 in a savings account! I, rather youthfully, still don’t know what I’m doing with my life. So how did something that felt so relative become so relentlessly, indisputably, factual?

My go-to drinks have all become old-fashioned-style cocktails and now, when Lee Hazlewood sings “Let those I-Don’t-Care days begin, I’m tired of holding my stomach in,” I really feel it, you know? I guess all it takes is a drink and a song for reality to set in.

Old-fashioned-style drinks are great. After life has formed a calloused skin shell of impervious disenchantment around your heart and soul, sometimes you just want to feel something, anything, and a good old fashioned is like putting a match out on your tongue and getting your shoulders massaged at the same time. But before I go too far into the wood-paneled study of “Daddy’s Had A Long Day” territory, as a reminder (mostly to myself) there is more to cocktails than a momentary, poorly-adhesive bandage slapped on the day-to-day. Cocktails give us a little ceremony, a ritual meant to dignify and elevate. And even while old-fashioned-esque drinks are certainly among the more serious and stiff, there is still plenty to play around with and discover within that glorious trifecta of bitters, sugar, booze.

The Fancy Free is a wonderful example of what a few modifications to a classic template can achieve. A fantastic old-fashioned variation to help us transition out of summer, it replaces the sugar cube with Maraschino liqueur, couples Angostura with a dash of orange bitters, and bumps the bourbon by a quarter ounce. The end result is something a little silkier and a little brighter than your classic old fashioned and yet, it also tastes like something out of another era, pre-technicolor, conceivable only in sepia tones—the desire to open an old book might strike you after a couple of sips.

I cut my maraschino liqueur with simple syrup, about 3:1 liqueur to syrup. You can jigger just under 1/2 ounce of Maraschino and top with a bar spoon of simple syrup. Like salt, a little bit of simple syrup can heighten the flavor of a liqueur, and help achieve a greater balance and harmony when making a mixed drink. The end result isn’t necessarily sweeter, just smoother.

Fancy Free

Starting with the bitters, pour all ingredients into a double-rock glass, add ice and stir 5-6 times. Express the oil from the orange twist on the cocktail and garnish.

*Unlike the heavy, dousing hand I encourage when it comes to using Angostura, you really only need a single conservative dash of Orange bitters to get the job done.