The Simple Way Frank Sinatra Liked His Martinis

Frank Sinatra was a crooner by night and a foodie by day (...and also night). Sinatra was an outspoken Jack Daniel's fan, even becoming an unofficial brand ambassador throughout his lifetime. Another common bar order for Sinatra was the Rusty Nail, a Scotch-based cocktail. Per the lore, one night when a bartender at the Four Seasons in Boston prepared his whiskey with too much ice, Sinatra reached his hand into the glass and physically scooped out the cubes. But, when it came to his martinis, Sinatra was singing a different tune: It had to be clear liquor on the rocks.

Sinatra reportedly ordered martinis from The American Bar whenever he stayed at The Savoy in London. As Savoy bartender Victor Gower recalls, via Thrillist, "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." (Sorry, vodka martini fans. You're still totally valid, though.)

"He liked things to be just-so," fellow Savoy bartender Peter Dorelli recounts, per the outlet. "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."

Persnicketiness aside, temperature is indeed a crucial factor for a successful (or even drinkable) martini, which makes the execution of an on-the-rocks martini somewhat hilarious. The drink is served in a rocks glass, ditching the eponymous V-shaped glass that has come to be linked with the martini. That long-stemmed glass is designed to maintain temperature control, and conversely, a rocks glass gets gripped in the sipper's warm fist, yielding premature dilution. Oh well.

While virtually unheard of in the modern bar scene, "martini on the rocks" was a fashionable, popular order during the 1960s. Even Sinatra wasn't immune to the trends of the times. The drink has its merits, too. The welcome dilution of the ice makes for a more open, expressive sip, softening the harsher edges of the martini's spirit-forward constitution.

The classic preparation of a martini on the rocks comprises 3 ounces of London dry gin and ¾-ounce of dry vermouth, stirred over ice in a mixing glass, then strained into an ice-filled rocks glass and garnished with a lemon twist. That's it. Other preparations swap the lemon twist for an olive skewer. Nowadays, in the seldom-seen corners of the modern bar scene where they do exist, martinis-on-the-rocks tend to be chilled with a single large ice cube, a la the Old Fashioned cocktail, another slow-sipper and subsequent slow-dilluter. Thirsty for more Blue Eyes lore? Here are 13 more foods and drinks that Frank Sinatra absolutely loved.