Here’s how to drink like the Rat Pack

From Frank Sinatra’s favourite Scotch whisky to Dean Martin’s cocktail of choice, here’s how to drink like the famous entertainers…

Before we take even one sip, let’s hear some quotes about drinking from the Rat Pack: “Alcohol may be man’s worst enemy, but the bible says love your enemy”; “You’re not drunk if you can lie on the floor without holding on”; “Alcohol gives you infinite patience for stupidity”; “If you drink, don’t drive. Don’t even putt”; “I feel sorry for people who don’t drink. When they wake up in the morning, that’s as good as they’re going to feel all day”.

Who said which? Who cares? Because, after a while — and several spirited bottles of whisky and wine — the many, motley members of the rambunctious Rat Pack begin to shake, stir and swirl together; blending together into one trimly tailored, Martini-mixing legend. And, if there’s one thing the informal band of entertainers did better than anyone else, it was drinking.

Founded in the late 1950s, the group got their name from Humphrey Bogart’s wife, Lauren Bacall — who, upon seeing the bedragged bunch return from a night in Las Vegas, said, “You look like a goddamn rat pack”. Over the years, members came and went. But the key core remained largely the same: Frank Sinatra, Dean Martin, Sammy Davis Jr, Peter Lawford and Joey Bishop. And the showmen knew how to have a good time.

“The whole world is drunk,” Dean Martin once said of the group’s popularity, “and we’re just the cocktail of the moment. Someday soon, the world will wake up, down two aspirin with a glass of tomato juice, and wonder what the hell all the fuss was about.”

But that hungover day is yet to dawn. Over sixty years later, and people still play Rat Pack records, watch Rat Pack films and tell Rat Pack jokes. We even drink Rat Pack drinks. So, if you’re looking for a little retro drinking inspiration this weekend, here’s how to drink like the Rat Pack…

Frank Sinatra may have loved Jack Daniels, but he also liked a Scotch

Ol’ Blue Eyes may be most famous for drinking Jack Daniel’s — the Lynchburg-based brand even released a ‘Sinatra Select’ edition of their world-renowned bourbon in 2012 — but he also loved a Scotch. The whole Rat Pack did. Sinatra’s first whisky love was Chivas Regal; he’d request a bottle backstage at every show he played in the 1950s, and the brand went on to sponsor his 1990 Diamond Jubilee tour.

But he also liked J&B Rare — and turned much of the Rat Pack onto the iconic green and yellow bottle. Herman Hover, owner of LA’s Ciro’s Nightclub, once revealed that Dean Martin was a fan of both Black & White Blended Scotch and Haig & Haig Pinchbottle before he began partying with Sinatra, who turned him onto the considerably more fashionable J&B.

Dean Martin knew his bourbon (but didn’t use it in an Old Fashioned)

Although Dean Martin’s drinking eventually contributed to his ill health, the performer’s signature ‘drunky’ routines were notoriously fake. Martin would hold a glass of ‘whisky’ (usually a weak scotch-and-soda or apple juice) on stage, and play up his tipsiness for laughs. But that didn’t mean he wasn’t a whisky aficionado.

In fact, while Martin may have been a more outward Scotch fan than Sinatra, he also shared his fellow singer’s fondness for bourbon. He enjoyed a frequent glass of Jack Daniel’s over ice — and even launched his own bourbon, Dino’s, in 1959 (part of a liquor line that also included a vodka and a Scotch whisky). Curiously, however, Martin preferred his Old Fashioned — a cocktail traditionally mixed with bourbon — made with Scotch.

Sammy Davis Jr loved a highball (and Japanese whisky to fill it)

While the rest of the Rat Pack enjoyed short, simple drinks — and lots of them — Sammy Davis Jr preferred to sip something a little more mixed. Frequently photographed with a highball in hand, Davis Jr’s drink choices were longer and often more involved than those of his fellow Rat Pack members.

It’s no coincidence, then, that Suntory Whisky employed the musician to sell its spirits from 1974 onwards. Japanese whisky is most commonly consumed in highballs, and Davis Jr became one of the first American celebrities to be used to advertise a Japanese product. The partnership even inspired Sofia Coppola when she wrote the Bill Murray-starring Oscar-winner, Lost in Translation. So, to drink like Sammy, go for Suntory.

The whole gang loved a Martini — but some with a twist

From Sammy to Sinatra — and even visiting members of the group including Jerry Lewis, Buddy Greco and Don Rickles — every drinker in the Rat Pack loved a Martini. Dean Martin even had Pepe Ruiz, the bartender at LA restaurant Chasen’s, mix him a special twist on the classic. Called the ‘Flame of Love’ Martini, it features vodka, sherry and so much orange peel you can see it stuffed into a highball above.

Sinatra’s order was similarly specific, yet a little more traditional. Victor Gower, bartender at The Savoy Hotel, recalled that Sinatra would “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 always filled with ice.”

But the signature cocktail of the Rat Pack was the Rusty Nail

Known by many different names, the Rusty Nail could be ordered as a ‘Mig 21’, a ‘Knucklehead’, a ‘Little Club No. 1’ or a ‘D&S’. Its origins in the 1930s are unknown, but it was so unpopular that even the idea of the drink disappeared for many years. But, when the Rat Pack assembled in the 1950s, the inimitable, potent blend of Scotch whisky and Drambuie returned in favourable, flavourful force.

In 1963, the then-chairwoman of Drambuie, Gina MacKinnon, publicly insisted that the drink should be called the ‘Rusty Nail’, and its associations with Sinatra and the gang saw it soar in popularity. Smoky and sophisticated, it would fan the flames of American mid-century cocktail culture and become synonymous with the Rat Pack. Follow the Difford’s Guide recipe here.

From Manhattans to Margaritas, Frank Sinatra was the cocktail king

Not only did Sinatra have a soft spot for a Rusty Nail — and frequently invite co-stars back to his trailer for ‘tini time — but he also had a talent for mixing other cocktails. Among his shaken and stirred repertoire: the Margarita (with lots and lots of tequila); the Old Fashioned (with a splash of water and two ice cubes); and the Manhattan (always Jack Daniel’s).

His favourite cocktail, however, was the simplest. Also using Jack Daniels, Sinatra would drop four cubes of ice into a leaded crystal glass, add two fingers of Jack Daniels, and top up with quality Poland Springs still water. “This is a gentleman’s drink,” he famously said of the simple serve. “This is nice.”

Looking further back? These are the best 1920s cocktails to revive this weekend…

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