Frank Sinatra, known as “Ol’ Blue Eyes,” was a man of refined tastes. His music, style, and persona epitomized sophistication, and his drink choices were no different. While many iconic performers have signature drinks, few have shaped cocktail culture like Sinatra. Frank Sinatra’s favorite drinks weren’t extravagant, but they were the epitome of class, reflecting his timeless elegance and deep appreciation for life’s simple pleasures.

The Love Affair with Jack Daniel’s

Above all else, and widely known, Frank Sinatra’s favorite drinks was Jack Daniel’s Tennessee Whiskey. His relationship with the brand began in 1947, when comedian Jackie Gleason introduced him to the whiskey during a night out. Sinatra fell in love with it immediately, famously referring to Jack Daniel’s as “the nectar of the gods.” He was rarely seen without a glass in hand, often sipping the drink between songs during his performances​ not only in Las Vegas, but everywhere else.

3-2-1 Drink Up!

Sinatra’s preferred way to enjoy Jack Daniel’s was through a simple and now famous method known as the 3-2-1: three ice cubes, two fingers of whiskey, and a splash of water. This classic concoction became known as “Frank’s Way.” While the 80-proof Jack Daniel’s Old No. 7 is the most common today, Sinatra preferred the stronger, original 90-proof version​. His loyalty to the brand was so profound that he was buried with a bottle of Jack Daniel’s when he passed away in 1998, cementing his legacy as the whiskey’s ultimate ambassador​.

Meticulous = Delicious

Sinatra often insisted on quality glassware, believing that fine whiskey deserved to be served in elegant leaded crystal. He was known to be meticulous about his drink—no more than four ice cubes, no more whiskey than two fingers, and always with a splash of still water​. If the drink was too strong, he would call it “Sammy Davis in a glass,” referencing his fellow Rat Pack member’s bold personality​.

A Taste for the Rusty Nail

While Sinatra’s fondness for Jack Daniel’s is well-documented, he also had a soft spot for the Rusty Nail, a cocktail popular among his Rat Pack friends. This drink, made with Scotch whisky and Drambuie (a Scottish liqueur with honey and herbs), was a regular choice during Sinatra’s visits to PJ Clarke’s in New York​. The Rusty Nail combines the smoky depth of whisky with the sweet complexity of Drambuie, finished with a twist of lemon peel. This simple yet flavorful cocktail became a signature of the Rat Pack and the mid-century cocktail scene​.

A Classic Martini with a Twist

Another of Sinatra’s signature drinks was the classic Martini, though he had a very specific way of enjoying it. Sinatra preferred Beefeater gin with just a hint of vermouth and a twist of lemon, always served on the rocks. Known for his appreciation of a well-made drink, Sinatra ensured his glass was always filled with ice, believing that it brought out the best in the flavors​.

A Timeless Legacy

Sinatra’s drink choices reflect the man himself—elegant, refined, and timeless. Whether sipping on Jack Daniel’s or enjoying a Rusty Nail, Sinatra knew how to drink with style. His love for simple, well-made cocktails has inspired generations, proving that sometimes, less is more. To drink like Frank is to embrace a sense of class, confidence, and a deep appreciation for the finer things in life.