Why the Manhattan Is Such a Classic Cocktail—and How to Make It the Right Way

The Manhattan is so much more than the sum of its parts. Standing stately in a classic V-shape cocktail glass, this cocktail is as majestic and sophisticated as the New York City borough it was named after. And yet, it is one of the simplest drinks to commit to memory: two parts American whiskey (some say bourbon, others say rye), one part sweet vermouth, Angostura bitters, and a cherry. Stir, strain, and sip—done.

Its power and allure are owed to the alchemy of those ingredients when combined. Think about it: Be it soft bourbon or spicy rye, both of these spirits pick up beautiful notes of vanilla and caramel from lingering long in American oak barrels. Then there's the herby, fruity fandango that is the oomph of vermouth, and the subtle, but piquant punch of bitters. Biting into a whiskey-soaked cherry at the end punctuates the whole experience with the most delicious kind of coda.

Bourbon vs. Rye

Most bars today choose bourbon as the base, but with the rise of rye (and the notion that many believe it was the original spirit used in the drink), you can play around with different American whiskeys. "I prefer rye because that's probably what the original was made with. There was less bourbon in the late 1800s than there is today, so rye would have been the original whiskey," says Frank Caiafa, author of The Waldorf Astoria Bar Book and the former bar director of the hotel's storied Peacock Alley.

But then again, the original recipe can be one of the hardest things to discern about a cocktail, especially one with a history as long as the stem on the Manhattan's pretty vessel. There are, however, a few theories about the this drink's beginnings.

The History of the Manhattan

The Manhattan definitely dates back to the 1800s, and likely to America. One of the tall tales touted around the drink's invention was that it was created for one Jennie Jerome—the future Lady Randolph Churchill and the mother of England's most famous prime minister—for the celebration of the election of New York Governor Samuel Tilden at the Manhattan Club.

But while the comely Ms. Jerome was indeed fond of rye whiskey and the Manhattan Club, there's proof that she wasn't even in the country, let alone the borough of Manhattan, on that occasion. Still, the Manhattan Club may well have invented the drink, and perhaps adds a little extra interest to the cocktail's origin story (which was probably far less exciting). "As far as the original story goes, I like the idea that it was invented at the Manhattan Club and named for it. There were other society clubs in New York then and most had bars, and often a house bartender who would create a popular cocktail for their members and name it after the club," says Caiafa.

Never Shake, Always Stir

The Churchills aside, there are some hard and fast facts about the Manhattan. One of the most important: Do not shake it (always stir). Spirits-centric drinks like the Manhattan and the Martini are stirred to add the proper chill and dilution from the ice, and also to keep to the drinks' crystalline aesthetic. (Who wants a cloudy Manhattan? Not even Manhattanites.) Caiafa has some other well-honed tips for this portion of the drink's recipe.

Stir Time

"Deciding how long a stirred cocktail should be stirred depends on the ice you use. Harder, drier ice should be stirred longer, about 30 seconds. For wetter, smaller cubes, 15 seconds is all you need," he says.

Serving Up vs. Over Ice

If you feel like such a spirit-forward drink served up is a little too heady for your tastes, pouring it over ice is perfectly acceptable. If you take this route, try this trick. "You can serve a Manhattan over ice, but then I'll up the whiskey amount to 2 1/2 ounces. You have to adjust for the longer dilution rate as it sits in the ice," Caiafa says.

Garnish With the Spirit in Mind

The iconic garnish for a Manhattan is a cherry—preferably, a proper Maraschino (not the neon-red banana split kind), Amarena, or brandied cherry, which is Caiafa's choice. Some Manhattan makers also use a twist. "I like both! I'll use a lemon twist if the Manhattan is made with rye, and an orange twist if I'm using bourbon. And a cherry, because who doesn't like the good cherry?" says Caiafa.

The Best Manhattan Riffs

Even a simple three-ingredient drink like the Manhattan is fodder for creativity. "You can make a Marconi Wireless with apple brandy instead of whiskey, a Cuban Manhattan with rum, a Rob Roy with Scotch instead of bourbon or rye, or a Paddy with Irish whiskey," says Caiafa.

Seasonal Bitters

In addition to trying different spirt bases, you can vary your bitters with the seasons, says Caiafa: "I like Angostura in winter, and orange bitters in summer!"