Certain cocktails seem to have their own gravitational pull—toward a season, a bar stool, a comfortable couch. Some might deem them workaday drinks. It’s not that the Rob Roy is lacking in fanciful appeal—poured into a long-stemmed cocktail or coupe, its auburn glow begs for dim lights, slow sipping and Chet Baker on the juke. But unlike its swinging socialite sister, the Manhattan, the Rob Roy is a little bit bookish—not quite a wallflower but certainly more brooding than bombastic.
When my three sisters and I were growing up, the Rob Roy was our parents’ nightly respite: one sipped before dinner with quiet conversation—kids sequestered to the TV room, because we had those back then—and made with a working person’s luxury of blended scotch (in our house, Dewar’s), sweet vermouth, bitters and a cherry, although the lemon peel might make the occasional appearance when the air turned tepid.
But while the children of Roy Roy devotees may carry a flame of nostalgia for the drink, that’s not the reason it’s hung in there for more than 100 years since its likely creation at New York’s Waldorf Astoria hotel.
Its endurance lies, in part, in its ease. “They’re simple to make,” says Frank Caiafa, the owner of cocktail consulting company Handle Bars NYC and the man who spent the last 11 years as Waldorf Astoria’s beverage director for Peacock Alley and La Chine. “It’s three ingredients: bitters, whisky and vermouth. You’re not really asking anyone too much to attempt it at home,” says Caiafa. “That’s an important reason drinks like that last so long.”
That simple cocktail likely came to be because of Waldorf Astoria’s original location on Fifth Avenue in the lower 30s from 1893 to 1929, conveniently perched smack within the Great White Way, the original well-lit section of the city devoted to the stage arts.
It was here, according to Caiafa, also the author of “The Waldorf Astoria Bar Book,” that a Herald Square Theatre production of an operetta named “Rob Roy” by the composer Reginald De Koven inspired the birth of a drink. It’s a tidy origin story, no doubt. And though it lacks the often-cited exclamations of fuzzy impossible-to-pin characters in drinking lore, it’s a fairly plausible scenario.
More interesting, though, is the role of the all-important key ingredient: vermouth. Without its growing popularity at the time, it and the Manhattan simply wouldn’t exist. That, according to Phil Greene, the author of “The Manhattan: The Story of the First Modern Cocktail with Recipes,” is really where it all began.
“This is a story of immigration,” says Greene. “Vermouth was an Italian import that no one in America had heard of until it appeared in the melting pot of the cocktail. It’s kind of like St-Germain today. Everyone started using vermouth then.” By the 1860s, vermouth cocktails began showing up in American bars. Soon after, we find evidence of the Manhattan cocktail. By 1894, says Greene, rye was swapped for scotch, and the Rob Roy was born. The original ratio of whisky to vermouth was one-to-one, but as time marched on and drinks got boozier, two-to-one became, and remains, the standard proportion.
So is a Rob Roy simply a Manhattan with scotch? Well, yes and no. As with any recipe, the whole secret to a tippling triumph is the way the ingredients play together. And when that ingredient is scotch, there’s a world of variation to be had.
“In the same way that a Martini is the quintessential gin drinker’s cocktail because it’s a love song to gin and to balance, the Rob Roy, and its Manhattan counterpart, is an ode to the spirits chosen and is meant to highlight the best of what’s in the glass,” says Andy Bixby, the cocktail director for Jack Rose Dining Saloon in Washington, D.C.
With blends, Bixby advises not to assume all are created equal. “Johnnie Walker Double Black is going to have a much more pronounced smoke component, whereas something like Compass Box Asyla will provide a more dry vanilla spice character,” he says. When considering a straightforward single malt, Bixby says to think about the overall tone that scotch lends to the drink. “A Lagavulin Rob Roy will be beefy, dense and smoky with almost caramelized meat notes,” he says. “The Glenmorangie Rob Roy we serve provides a nice balance between the gumball acidity of the Cocchi Storico Vermouth di Torino and the honey, stone fruit characteristics of the Glenmorangie Original.”
At New York whisky-centric sister spots Fine & Rare and The Flatiron Room, Monkey Shoulder, a blend of Speyside single malts, is a Rob Roy favorite. “A lot of our food and drink at Fine & Rare is full-flavored, and Monkey Shoulder does a nice job of holding its own against beefy Italian vermouths that I tend to reach for at the bar,” says bar manager Joseph Bennett.
At The Flatiron Room, bar manager Young Kim likes to switch things up when the weather gets cold. “The slightly peaty Black Bottle and bolder and more herbal Carpano Antica garnished with a brandied cherry goes well when the weather is cold.”
Oh, but the bitters. The aromatic sort are often the go-to, but for Caiafa, they are just too overpowering for your average blended scotch. For his Waldorf Astoria version, orange bitters hit the sweet spot. “Orange doesn’t blow the scotch out of the water; it’s much kinder,” he says. “But that’s the signature of a great cocktail—that it’s a little pliable. It doesn’t have to be exactly what it began as to retain its soul.”