My grandfather Harry Ladehoff, keeper of the Old Guard, wore bow ties and drank manhattans. He only drank them on special occasions and usually ordered a double—guaranteeing a certain level of buttoned-up jollyness by the end of a birthday or the Fourth of July. Born in 1901, he entered into his drinking prime (his 20s) with truly terrible timing.

Prohibition fundamentally altered the way Americans thought about and consumed alcohol. And the manhattan cocktail—the eponymous tipple of the United States’ liveliest hub for business, immigrants, and organized crime—was one of its prime targets. Through the 1800s to that fateful day in 1919 known as the start of Prohibition, it had been made one way and one way only: rye, sweet vermouth, bitters.

Somewhere around the 1900s, the introduction of maraschino cherries changed a lot—including cocktails and making sundaes … better, somehow? They also made a lasting appearance in the manhattan. And then bourbon entered the picture, too.

The De-Evolution of New York’s Most Popular Drink

Booze in America was likely terrible during Prohibition (and, arguably, for a long, long time to come, up until rather recently), and fruits like the maraschino cherry were the perfect way to disguise the taste. This is why the old-fashioned was thus desecrated for years to come; the manhattan suffered a similar fate.

Though many of these classic cocktails have benefited from a recent resurgence in the old ways, the manhattan cocktail (with or without maraschino) maintained a quiet but steady presence, as evidenced by drinkers like Grandpa Ladehoff. Somehow, it retained a reasonable level of popularity through the war, the midcentury, and even the terrible, terrible time it was to drink things in the ‘80s and '90s. The manhattan was a secret handshake between those who remembered the old and somehow dealt with the new. It was a salute to simpler times.

The Potential to Be Divine

Like many classics, its origins are unclear, and a collection of legends and claims surround the initial creation of the drink. Thought to be invented at the Manhattan Club back in 1874 for Winston Churchill’s mom (yeah, who knows), the drink wore the name of its incubator and deep New York roots, but little else remained the same.

The subbing of bourbon can be blamed simply on bourbon’s rise in popularity and rye’s sharp decline. Until the end of the 20th century, rye had practically disappeared, and our beloved manhattan had become too sweet and was largely unpopular.

As cocktail historian David Wondrich would put it, the manhattan is “is as close to divine perfection as a cocktail can be”—but only when built properly. And by properly, he means with rye.

This brilliant, original cocktail is believed to be the first to use vermouth as a modifier and supplement to its base spirit, predating the martinez, the martini, and the Rob Roy. And by playing with the nearly endless varieties and measurements of bitters, vermouths, and whiskeys, you can create a giant portfolio of cocktails that are each unique in their own little ways.

Certainly some drinkers may disagree, but to me (and Wondrich), the original, unadulterated iteration of this drink perfectly balances the aromatic, sweet, and spicy. The result is what Wondrich would describe as bold and fortifying yet as relaxing as a deep massage.

Where to Drink a Manhattan

In the good old days, my family would often go to the Como Inn, just off the Kennedy Expressway in Chicago, and sit tucked away in a magical little booth where grandpa could get semiprivately sloshed and we could all pretend we were in the mafia. Sadly, the Como Inn met the wrecking ball years ago. Fortunately, you can find a manhattan cocktail just about anywhere. For an especially good one, try these old-school places, whose settings sweeten the deal by reminding us how we got here—if not how very far we’ve come.

P.J. Clarke’s (Third Avenue location), New York, NY
The original location of P.J. Clarke’s has operated as a bar since 1882, and in the mid-20th century, it was a destination for stars such as Elizabeth Taylor and Nat King Cole. These days, the tie-clad bartenders are “trained to be gentlemen before barmen,” but they also make a mean manhattan. They’re gentlemen, after all.

Bryant’s Cocktail Lounge, Milwaukee, WI
David Wondrich once posited that Bryant’s might be “the darkest bar in America.” Very much adhering to old-school traditions—including cocktail recipes so secret, Bryant’s doesn’t even have a drink menu—it was originally opened back in 1938. You can and certainly should order anything here, but drink at least one manhattan while you sway in your seat to the sounds of old-school R&B.

Elixir, San Francisco, CA
Since 1858, this corner spot has operated as nothing but a saloon, unlike many of the city’s oldest bars, which have changed hands and identities from grocers to cafés and otherwise. But since you’re not just looking for a history lesson, Elixir also has 330 different types of whiskey on its old shelves, giving manhattan drinkers a seemingly endless amount of possibilities (though you should probably still choose rye).

Recipe for a Rye Manhattan

+ 2 oz. rye whiskey (Like sports allegiances and religion, whiskey is a personal choice. But you could always use Rittenhouse 100 Proof Bottled in Bond.)
+ 1 oz. sweet vermouth (Try Punt e Mes, an Italian vermouth that delicately negotiates the line between sweet and bitterly herbal.)
+ 2 dashes Angostura bitters

Build all ingredients in a stirring vessel filled with ice. Stir well and strain into a chilled rocks glass with fresh ice (if serving on the rocks) or coupe (if serving up). Garnish with a lemon twist or Luxardo maraschino cherry. Don your bow tie and drink up.

Photo by Andrew Nawrocki, Groupon