The Old-School Cocktail The Rat Pack Loved

Although the original Rat Pack was dreamt up in the 1950s and centered around Humphrey Bogart and Lauren Bacall, it's the 1960s Pack, composed primarily of Dean Martin, Frank Sinatra, Sammy Davis Jr., Peter Lawford, and Joey Bishop that most people associate with the title. These famous rascals became fixtures in Las Vegas, where they performed regularly, during the swinging decade. Palm Springs was also their playground, where they frequented an iconic supper club called The Purple Room. The group was exceptionally talented, but their notorious capacity for partying may be what many people remember them by. Big smokers, and even heavier drinkers, each member seemed to have an affinity for certain boozy drinks. And if the Pack as a whole was known for collectively quaffing one drink, it was a Rusty Nail. 

The Rusty Nail had been around since the 1930s, but it was largely forgettable. However, when the Rat Pack started drinking them publicly a few decades later, so did everyone else. The classic Rusty Nail recipe comes together with Scotch and Drambuie liquor, which itself is Scotch-based and flavored with honey, herbs, and spices. It's strong, you could even say it's tough as nails to get down your gullet if you don't drink a lot of alcohol, but we know the Rat Pack was well seasoned in strong drinks.  

The origin of the Rusty Nail is a little murky, but many believe the first time it appeared, it was called something else entirely. At the 1937 British Industries Fair held in New York, a cocktail known as the B.I.F. (named for the fair) was dreamt up and made with Scotch, Drambuie, and bitters. It has also been associated with artist Theodore Anderson who requested it at a bar in Hawaii in 1942, which is interesting since the Rusty Nail has zero essence of a tropical paradise. However, it's unclear what the drink may have been referred to here. 

Before becoming associated with the Rat Pack, Scotch and Drambuie wasn't considered a well-known cocktail order, but those who drank it knew the combination by all sorts of names, including the Knucklehead, Little Club No. 1, and the Mig-21. The D&S was also used, short for "Drambuie and Scotch," until Drambuie trademarked the "Rusty Nail" in 1963, which is right around the time Frank, Deano, and Sammy would have been throwing them back with gusto.

If you want to try this iconic cocktail at home, you might need to play with the ratio of each liquor to see what pleases your palate. While Drambuie is strong, it's also very sweet, so a 1:1 ratio of Scotch to the liqueur might be too sugary; start with less Drambuie and build from there. You can also add some brightness with a squeeze of lemon, or tame everything down with a splash of club soda.