How to Drink Like Frank Sinatra — And Recover Afterwards

“I feel sorry for people that don’t drink, because when they wake up in the morning, that is the best they are going to feel all day.” 

“Alcohol may be man’s worst enemy, but the Bible says to love your enemy.”

“Basically, I’m for anything that gets you through the night – be it prayer, tranquilizers, or a bottle of Jack Daniels.”

Frank Sinatra

These are just some of the quotes about drinking that Frank Sinatra is known for. It wasn’t just his famous voice and his acting chops, Frank Sinatra was almost just as known for his love of a good, stiff drink.

Want to drink like Ol’ Blue Eyes? Here’s how he would have done it.

Pop Open a Jack Daniels

How much did Sinatra love Jack Daniels? Enough that he was buried with a bottle of it. According to legend, Sinatra was such a fan that he once got on stage and proclaimed, “Ladies and gentlemen, this is Jack Daniel’s, and it’s the nectar of the gods.”

Sinatra’s choice Jack Daniels cocktail was simple: ice, whiskey, and water. Here’s how to make a Jack Daniels drink just like Sinatra:

  1. Choose a nice piece of glassware. Sinatra believed that good glassware equals good drinking.
  2. Place no more than four ice cubes in the glass. 
  3. Pour no more than two fingers of Jack Daniels over ice.
  4. Fill the remainder of the glass with high quality still water. 
  5. Let the drink sit for two minutes before sipping.
  6. Drink, refill, repeat.

The Sinatra Martini

Sinatra was a Jack Daniels man, but he enjoyed other liquors as well. Here are the ingredients for a martini prepared just the way that Sinatra liked it:

  1. Gin, not vodka; Sinatra preferred using Beefeater Gin for his martinis.
  2. Add just a splash of vermouth.
  3. Serve on the rocks; Sinatra liked his martinis ice cold.
  4. Add a twist of lemon.
  5. Drink, refill, repeat.


  • 3 oz. Beefeater gin.
  • ¾ ounce dry vermouth.
  • 1 small strip of lemon peel.
  • Mixing glass full of ice.

Flame of Love Cocktail

While a bartender at the Hollywood restaurant Chasen’s created this drink recipe for Dean Martin, not Sinatra, Sinatra was known to enjoy this creation as well. Here’s how to mix the Flame of Love cocktail:


  • 2 ounces vodka.
  • ¼ ounce fino sherry.
  • Several large strips of orange peel (for garnish.)

Imbibe Magazine gives these directions for the drink:

“Rinse a chilled cocktail glass with sherry, and discard excess. While squeezing a large strip of orange peel over the sherry-rinsed glass, use a match to carefully flame the oils spraying into the glass. Repeat several times with additional peels. Stir the vodka with ice until chilled, then strain into a prepared glass. Flame a final orange peel over the finished drink, then garnish.”

However, if you drink like Frank Sinatra, then there’s one more thing you need to know: How to recover afterwards? The crooner was known for his hard boozing ways, and while we know that can be fun, we also know that the day afterwards can feel… less fun.

With help from Douglas Laboratories, Klaire Labs, and Aubrey Organics, you can stay in tip-top shape and recover more quickly … even after a night of drinking like Frank.

Douglas Laboratories

You need more than Jack Daniels to have a good night drinking: you also need Alpha-Lipoic Acid. Alpha-Lipoic Acid from Douglas Laboratories is a dietary supplement that may help the body scavenge free radicals and convert glucose into energy. ALA is an antioxidant that helps your body produce glutathione, which helps support liver detox and boosts the immune system. 

Klaire Labs

Another way to pre-game (in a way that may help protect you from a nasty hangover the next day. Try N-Acetyl-L-Cysteine from Klaire Labs. NAC is a super antioxidant and a precursor to glutathione, which provides liver support.

Aubrey Organics

Even if you load up on the right supplements, a super late night of drinking like Frank might leave you looking a little bleary-eyed in the morning. Fix that with Lumessence Eye Cream from Aubrey Organics. It was designed to firm and brighten the delicate skin around your eyes and reduce the appearance of dark circles and fine lines. And for men, check out Men’s Stock Daily Rejuvenating Eye Cream.