Brandy Alexander
Credit: © Frances Janisch

The perfect nightcap is different for everyone. For some it’s a stomach-settling shot of Fernet Branca, for others it’s a perfectly crafted Manhattan and for many it’s whatever is left in the bottle.

This past Tuesday night at the inaugural Sip a Nightcap competition presented by Santa Teresa, four judges including Leo Robitschek, of Eleven Madison Park and The NoMad, and “King Cocktail” Dale DeGroff judged the ultimate nightcap to be Jessica Gonzalez’s Fortune Teller cocktail: a simple but powerful mix of Santa Teresa 1796 rum, Cynar (an artichoke-based Italian liqueur) and Bonal (a bitter French aperitif wine). It is exactly what Robitschek looks for in a nightcap: Four ingredients or less. Strong and stirred. “Something that makes you want another sip but also doesn’t make you want to drink it too quickly.”

While Gonzalez’s drink falls in line with the modern cocktail trend of brown and boozy, nightcaps weren’t always like that. Here, cocktail historian DeGroff shares four examples of some historic nightcaps that probably wouldn't have stood a chance in the competition.

Coffee Cocktail “It was half Cognac, half port, an egg and a teaspoon of sugar, shaken very hard. There was no coffee in it. They called it the coffee cocktail because it looked like coffee with cream and sugar. That was a nightcap from the turn of the century from the 19th to the 20th—when everything was richer and sweeter.”

Stinger “Half Cognac, half white crème de menthe, shaken very hard, served over crushed ice. In the ’70s and ’60s we were eating these rich French foods, so when you got to the end of a meal of wine and multicourses and cheese and creamy this and saucy that, you had this minty, icy cold Cognac–crème de menthe drink. It was kind of an adult after-dinner mint.”

Frappés “In the ’60s you had women—mostly—who after dinner would order frappéed liqueurs like green crème de menthe and white crème de cacao. It was a crème over crushed ice.”

Brandy Alexander “Around the same time as the frappés, the last thing you had at night if you were a kid out with a phony ID was a Brandy Alexander: Cognac, white crème de cacao and heavy cream, shaken.”