The Strict Way Frank Sinatra Requested His Martinis

In the age of big band and swing, Frank Sinatra was as cool and smooth as a guy could get. In line with the chic party vibe of the Rat Pack era was the Italian-American singer's drink of choice: a gin martini. As commonplace an order as it was by the 1950s, Sinatra had very specific requests for his favorite libation.

According to Victor Gower, a former bartender at The American Bar at The Savoy in London, establishments would be given Sinatra's drink order ahead of his arrival. "He never spoke directly to us," Gower told The Cocktail Lovers. "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 ... He'd go for a classic martini — Beefeater gin with a shadow of vermouth, served on the rocks with a twist of lemon."

It's similar to a classic Martini cocktail, as it has gin, dry vermouth, and a lemon twist. The main difference was that it was served on the rocks, or over ice, instead of being stirred with ice and strained, called straight up. Gower says the glass had to be filled with ice to get Sinatra's approval. "His martini had to be very dry and very, very cold. The temperature ... was very important. So was the amount of liquid in his glass. If one small detail was wrong, everyone would know about it," he claimed.

Although unconventional, Frank Sinatra's martini on the rocks is a relic of his time. In post-WWII America, it was more commonly ordered. Throughout the 1960s, bars and liquor brands noted the trend, advertising with martinis on the rocks in mind. If you're skeptical, consider the fact that ice keeps the drink colder for longer than a simple stir. It's also easier to prepare and clean up after a martini on the rocks, since there's no stirrer or strainer left behind.

Of course, as the ice melts, it dilutes the notably potent drink, but that was part of the appeal decades ago. Modern-day imbibers who prefer Sinatra's version like it for this reason, too, as it makes the drink more sippable for casual occasions. Some also love forgoing the martini glass's triangular design for a rocks glass. Others prepare rocks martinis when they haven't pre-chilled the gin or vodka in the freezer.

Despite Sinatra's pickiness, he had a broader taste for alcohol than you'd imagine. The crooner was a major proponent of Jack Daniel's. In fact, Sinatra liked the whiskey so much he was buried with it, along with a pack of Camel cigarettes, a lighter, and ten dimes to make pay phone calls from the beyond. He'd order whiskey on the rocks too, often at some of his favorite restaurants in the U.S., which included a number of glitzy steakhouses, no-frills bars, and Italian bistros.