There are certain families into which nearly every cocktail falls: sours, slings, highballs, daisies, bucks and so on. Each is governed by a requisite construction and/or signature ingredient. But every so often, a cocktail comes along that defies convention, adhering neither to an expected build nor tried-and-true flavor combinations. They’re drinks that shouldn’t work, but against all odds, they do.
Consider, for example, the Chauncey. The early 20th-century formula stands out for its unusual triple-threat base consisting of equal parts gin, whiskey and Cognac. To that is added sweet vermouth and two dashes of orange bitters for a highly unusual, supercharged nightcap that, according to bartender Frank Caiafa, “is a drink just like any other drink—only more so.” Just as unlikely is the Yellow Parrot, an equal-parts mixture of absinthe, yellow Chartreuse and apricot liqueur that has nevertheless stood the test of time, becoming a fan favorite at Brooklyn’s Maison Premiere. It’s joined on the list of oddball equal-parts cocktails by the Angel’s Tit, a blend of maraschino liqueur and heavy cream dosed with a barspoon each of fernet and Cherry Heering that—though typically a layered drink—finds a modern audience when shaken and served up.
Some historic equal-parts formulas, meanwhile, necessitate minor tweaking to resonate with today’s drinkers. The Earthquake, for instance, was conceived as an even split between Cognac and absinthe, the brainchild of Henri de Toulouse-Lautrec, an early advocate of American cocktail culture. In Chantal Tseng’s adaptation, however, Cognac out-measures absinthe two-to-one and a lemon twist lends a crisp, dry finish to the spirit-forward mixture.
Though historic cocktail books are responsible for many of today’s nonsensical builds, there are more modern contributions to this class of drink, too. The Trinidad Sour, for instance, builds off of a full ounce and a half of Angostura bitters, complemented by an ounce of orgeat, three-quarters of an ounce of lemon juice and a mere half-ounce of rye whiskey. Despite its unusual makeup, the Trinidad Sour has landed on menus the world over, becoming, according to Robert Simonson, “perhaps the most famous, and widely served, of the modern cocktails that use aromatic bitters as the base.”
While the Trinidad Sour may be the most widely served, the Melbourne-born Death Flip is likely the most inconceivable in a category of cocktails that make no sense on paper, but come together in the glass. Knowing this, the drink’s home bar, the Black Pearl, did not list the ingredients—tequila, yellow Chartreuse, Jägermeister and a full egg—on the menu, opting instead for this ominous description: You don’t wanna to meet this cocktail in a dark alley. Plenty of people took the bait, and many ended up liking the unusual cocktail, earning the Death Flip the recognition of being the only flip to ever reach modern classic status.