Hit Me With Your Worst Shot

Knocking back a shot of liquor is a means to an end, the shortest distance between sobriety and a body-warming buzz. After a long, torturous day at the office, I appreciate the swiftness with which a 100-proof bolt of peppery Rittenhouse Rye recalibrates my mood.

But I've never had a day bad enough to make me want to glug a chunky Cement Mixer (lime juice–curdled Bailey's Irish Cream), a Liquid Steak (the unholy alliance of Bacardi 151 and Worcestershire Sauce), or Hungary's Zwack. The syrupy herbal liqueur makes drinking straight Jägermeister seem as easy sipping as Coors Light.

When it comes to shots, drinking them too often seems like a type of torture. Part of the blame is due to rites of passage. On their 21st birthday, newly legal drinkers are typically forced to glug rank concoctions, the more misguided the better. How else can you explain the Alligator Sperm, which is composed of melon liqueur, pineapple juice, and a dribble of cream? Happy birthday! Now vomit.

Other times, the supposed cure to a hangover is worse than the affliction. Case in point: the supposedly restorative Prairie Oyster. The chug-it blend of Tabasco, Worcestershire sauce, and a raw egg was originally devised as a morning-after pick-me-up, though I bet you can't keep the medicine down.

And certainly bartenders have no shortage of head-pounding tricks up their sleeves, one of them being the Pickleback. It takes perfectly good whiskey and pairs it with a chaser of briny pickle juice — a salty one-two punch that repulses as many imbibers as it head-scratchingly attracts. Even more mystifying is the sobering knowledge that thousands of fearless drinkers have glugged the house specialty at Canada's Sourdough Saloon: the Sourtoe Cocktail. A shot glass filled with Yukon Jack whiskey is finished with a shriveled salt-preserved human toe. Gulp until the digit taps your lips. And don't open them any wider.

Here are 10 shots and and liquors that are truly tough to swallow.