Frank Sinatra's Biography

Frank Sinatra, legendary crooner and member of the Rat Pack, was a famously picky drinker, but that didn’t stop him from enjoying his booze in large quantities once you got the order right.

The Hoboken, New Jersey native (known by many nicknames, perhaps chief among which was “Ol’ Blue Eyes”) got his start in the swing era of the late 1930s. By 1943, he had a solo deal with Columbia, and released his debut album, The Voice of Frank Sinatra, in 1946. Sinatra found fame in Las Vegas as a member of the Rat Pack in the 1950s, and went on to become an Academy Award-winning actor.

Throughout his career, Ol’ Blue Eyes delighted in all kinds of cocktails. He reportedly liked his Martinis made with Beefeater gin, “a shadow of vermouth” (according to Victor Gower, head bartender at the Savoy Hotel’s American Bar), and took them on the rocks with a twist.

But as you may have heard, Sinatra’s favorite drink was Jack Daniel’s—but he didn’t just sip it any which way. His exacting specifications were as follows: place four ice cubes in a snazzy crystal glass (any more and he’d take the extras out, explaining to the bartender that he “wanted to drink, not skate”), add two fingers of whiskey (no more, no less—he referred to heavy pours as “Sammy Davis in a glass”), and fill the rest of the glass with bottled water. He called this concoction “The Black Ass of Jack Daniel’s,” and seemed to enjoy it more than any other.