The origin of the Pickleback (also known as the Piskey Whickle) remains, to this day, shrouded in mystery. A simple enough one-two punch, the Pickleback is by definition a shot of whiskey followed immediately by a shot of pickle brine. As delicious as this sounds, some still need a little convincing. Jonathan Swift once said, “Twas a brave man who first ate an oyster”, and by this logic, I like to imagine that the first ever Pickleback was drunk sometime around the 17th century when men were stouthearted and pickles abundant; perhaps by a fearless traveler who walked into a dimly candlelit bar and bravely mistook the salty brine for a glass of water.
Alas, while the true history of the Pickleback may never be known, the first bartender to champion the cause was Reggie Cunningham. In 2007, Reggie worked for the Bushwick Country Club in Brooklyn, NY. At the time, the bar’s basement also served as storage for McClure’s pickles next door. According to Reggie, he was feeling particularly hungover one day, eating a jar of pickles behind the bar, when a “trashy Florida redneck chick” insisted he pour some of the juice into a glass and join her in what is widely considered to be the very first Pickleback. The drink was instantly popular among industry folk who claimed not only that the pickle juice improved the flavor of the whiskey and counteracted some of the bite, but also that this miraculous libation was essentially hangover proof. Though the Pickleback was originally poured with Old Crow Bourbon, Jameson is now the standard and you can get it along with a shot of house pickle brine at Au Cheval.
— Danielle Zuckerman