This 2-Ingredient Cocktail Was Frank Sinatra's Go-To

Frank Sinatra is best remembered for his voice, music, and style, but he also had a reputation for being an avid — and particular — drinker. For instance, he had a strict way of requesting his martinis: frigid, extra dry, and over ice. Sinatra also liked Jack Daniel's whiskey so much, he was buried with a bottle of the stuff. Still, he was perhaps fondest of the rusty nail cocktail.

A rusty nail is a mix of Scotch and Drambuie, which is a sweet Scotch-based liqueur with notes of herbs, smoke, and spices. Sinatra was as much a fan of Scotch as he was whiskey. One of his favorite brands was Chivas Regal, which he had on hand at every gig he played in the 1950s. Fellow singer Dean Martin introduced him to Black & White Blended Scotch and Haig & Haig Pinchbottle once they started performing together. Sinatra was also a fan of J&B Rare, which the rest of the Rat Pack (including Martin, Sammy Davis Jr., Joey Bishop, and Peter Lawford) eventually came to enjoy.

In Sinatra's heyday, the rusty nail had many names, like Little Club No. 1, Mig 21, Knucklehead, and D&S. It hit the U.S. bar scene in the 1930s without much impact, but as Sinatra and his crew became associated with the libation in the 1950s, its popularity increased. Once the former chairwoman of Drambuie cemented the rusty nail's name in 1963, which some theorize came from its brown color, it quickly took off.

The rusty nail is a relic of Frank Sinatra's time. It's not on most bar menus today, nor is it often ordered. But decades ago, it was all the rage, popping up everywhere from New York City to New Orleans. While it's uncertain when and how it was invented, some believe the drink dates back to the 1937 British Industries Fair trade show.

The Rat Pack caught on to Sinatra's go-to drink without much convincing. Dean Martin was already a big proponent of Scotch; he even used it in place of bourbon in an Old Fashioned. Sammy Davis Jr. was fondest of Japanese whiskey. Although different from Scotch, it's made with Scottish production methods and both liquors have a smoky edge that likely helped the singer transition from one to the other with ease. 

Traditionally, the rusty nail is two parts Scotch and one part Drambuie, but some prefer pouring the pair in equal parts or with four times the Scotch for a drier flavor. While part of the cocktail's allure is that it only requires two ingredients, some add a few drops of Angostura bitters and a lemon twist. Regardless, it should be stirred with ice to chill, then strained over ice in a rocks glass. To make like Sinatra, try our rusty nail cocktail recipe with one of his favorite Scotches (Chivas Regal is the most affordable and easiest to find).