How to Drink, According to Frank Sinatra

Ol’ Blue Eyes (aka Mr. Francis Albert “Frank” Sinatra), knew a thing or two about living life to the fullest. “You only go around once,” he once famously said, “but if you play your cards right, once is enough.” Sinatra played many of his cards in bars across the country—drinking, gallivanting with the Rat Pack and generally holding court. They didn’t call him the Chairman of the Board for nothing.

Sinatra was such a beloved regular, in fact, that he even had his own chairs and barstools at some of his more frequented watering holes. If that doesn’t earn you an honorary Ph.D. in drinking, then we don’t know what does. Thankfully, Sinatra graciously shared a few nuggets of his expertise, both in quotes and song.

Here, how to drink, according Il Padrone, Frank Sinatra.

General Quotes on Drinking from Frank Sinatra

Sinatra was always ready with a brilliant one-liner. A few of those centered on everyone’s favorite topic: booze. Here are a few of our favorite quips.

  • “I feel sorry for people that don't drink because when they wake up in the morning, that is the best they’re going to feel all day.”
  • “Alcohol may be man's worst enemy, but the bible says love your enemy.”
  • “Basically, I'm for anything that gets you through the night—be it prayer, tranquilizers or a bottle of Jack Daniel's.”

Sinatra on Jack Daniel’s

Jackie Gleason allegedly first introduced Sinatra to Jack at Toot Shor’s bar in New York. It was love at first sip and soon became Sinatra’s favorite spirit. He was even buried with a bottle of Jack Daniel’s Black Label. Here, a few quotes from Sinatra about his beloved Jack.

  • "This is a gentleman's drink.”
  • According to Tales of the Cocktail, in 1955, Sinatra announced onstage, “Ladies and gentlemen, this is Jack Daniel’s, and it’s the nectar of the gods.” The next year, Jack Daniel’s annual distribution doubled from 150,000 cases to 300,000.

Sinatra’s Martini

While Sinatra favored the brown stuff, he also made room for Martinis, which he often enjoyed at The Savoy hotel in London. According to Savoy bartenders Victor Gower and Peter Dorelli, Sinatra was very particular about how his drink was made.

  • Gower: “Frank was a regular guest. Whenever he was in London, he’d stay at The Savoy and come for a drink in The American Bar, but he never spoke directly to us. He’d either stand at the bar or take a table in the middle of the room for him and his guests. Where he positioned himself might change, but he was always very particular about his choice of drinks. He’d go for a classic Martini—Beefeater gin with a shadow of vermouth, served on the rocks with a twist of lemon. And we had to make sure his glass was filled with ice.”
  • Dorelli: “He liked things to be just-so. He’d have the same room on the fifth floor of the hotel, the same waiter at the bar and the same drinks. I remember his Martini had to be very dry and very, very cold—the temperature of his Martini was very important. So was the amount of liquid in his glass. If one small detail was wrong, everyone would know about it.”

In Song

Sinatra’s love affair with alcohol was reflected not only in his life, but also in his songs. Here are a few of the best boozy lines from some of Sinatra’s top tunes.

  • “I Get a Kick Out of You” (Songs for Young Lovers, 1954):
    I get no kick from champagne.
    Mere alcohol doesn't thrill me at all.
    So tell me why should it be true
    That I get a kick out of you?
  • “Drinking Again” (The World We Knew, 1967):
    Drinkin' again and thinkin' of when, when you loved me
    I'm havin' a few and wishin' that you were here
  • “One for My Baby” (Recorded in 1947, and featured in the film Young at Heart in 1954):
    We're drinkin', my friend, to the end of a brief episode
    Make it one for my baby and one more for the road
  • “Very Good Year” (September of My Years, 1965):
    But now the days grow short, I'm in the autumn of the year
    And now I think of my life as vintage wine from fine old kegs
    From the brim to the dregs, and it poured sweet and clear
    It was a very good year
  • “Did You Evah” (Featured in the film High Society as a duet with Bing Crosby, 1956):
    Crosby: “I drink to your health”
    Frank: “Nah, let’s drink to your wealth”
  • “Come Fly with Me” (Come Fly With Me, 1958):
    Come fly with me, let's fly, let's fly away
    If you can use some exotic booze
    There's a bar in far Bombay
    Come fly with me, let's fly, let's fly away