A maraschino-laced cousin of the Old Fashioned, the Fancy Free trades sugar for the nutty, faintly cherry depth of maraschino liqueur and braces bourbon's warmth with both orange and aromatic bitters. Stirred down over a large cube and brightened by an expressed orange twist, it drinks spirit-forward and only lightly sweet — in effect an Improved Whiskey Cocktail, with the cherry-almond note lifting it toward something more floral.
Garnish: Orange Peel
Stirred · Old Fashioned · Large Cube
add
Combine bourbon, maraschino liqueur, orange bitters, and aromatic bitters in a mixing glass with ice.
stir
Stir until well chilled and properly diluted, about 20-30 seconds.
strain
Strain into a chilled Old Fashioned glass over a large ice cube.
express
Express the oils of an orange twist over the surface.
garnish
Drop the orange twist into the glass.
No individual inventor is on record for the Fancy Free, which belongs to the broad family of improved whiskey cocktails. Its earliest known appearance in print is Crosby Gaige's Cocktail Guide and Ladies' Companion of 1941 — and Gaige, a Broadway producer and publisher, gathered recipes rather than devising them. That wartime version was shaken and poured into a stemmed glass with a sugared rim, whereas bartenders today have largely moved it into a rocks glass and stir it over ice.