It’s Okay to Cask: What Would Frank Sinatra Drink?

It’s Okay to Cask: What Would Frank Sinatra Drink?


Another entry from ManBQue member The 40 Year Old Virgin, in his ongoing quest to help you appreciate fine whiskies, whiskys, and the like. Today: ruminations on a legend.

Drink like a man.

With that simple admonishment, Frank Sinatra summed up his theory of the Drinking Life. Now, “drink like a man” can mean all sorts of things, and I’ve been able to dig up quite a few interesting and contradictory stories whilst researching The Chairman’s drinking habits.

That Frank – excuse me, Mr. S – liked to drink is undeniable. The legend of the hard-partying, serious-drinking Rat Pack boys is born out of truth. Sinatra socialized 7 days a week, and by socialized I mean drank:

“…it was hard liquor that powered the Pack. (…G)asoline was the primary fuel, supplemented with dry martinis and scotch.”

So what did Sinatra prefer? My primary research tool being the Internet, there are some crazy opinions being offered, like this one:

“Manhattan (Dry version) This was the drink of choice for Frank Sinatra and his homeboys in the Rat Pack. Classic drinks stay in style, so stick with a Manhattan when all else fails. If you have a great blended whiskey on hand, like Johnnie Walker Blue Label, even better.
¾ oz. Dry Vermouth 1½ oz. Blended Whisky
How to make it: Stir with ice and strain into a cocktail glass. Serve with an olive.”

Seriously? The inaccuracies here are crippling. A “blended whiskey” like Blue Label (a blended Scotch actually) which wasn’t even available until 1992? And the drink; a Scotch Dry Manhattan (more properly called a Rob Roy), blended 2-to-1, and garnished with an olive? First, yuck. If people drank this shit in the ’50s, no wonder they looked like they weren’t having any fun. Second, Frank is known to have preferred a well-mixed cocktail (bartenders were advised not to try and get friendly with Mr. Sinatra by pouring a heavy drink), and he generally liked just the merest hint of dry vermouth. He liked his cocktails just so, as this reminiscence by a bartender from the American Bar at the Savoy Hotel in London shows:

“…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.”

However, the “Manhattan Theory” is supported by a crazy desert resort that created a bunch of cocktails in the Image and Likeness of the Chairman. They tout that “One of Sinatra’s drinks of choice was the Dry Manhattan.”

However, this Manhattan is made more properly, with Canadian whiskey, bitters and dry vermouth, garnished with a lemon. I believe he could have perhaps had one or two of these in his life, though I wouldn’t call it his “go-to” drink…(Note: check out their website for other drinks “inspired” by Frank, and weep that his memory could be tarnished by the likes of them…)

Its when you start searching past page 3 of the Google results for “Frank’s Favorite Cocktail” that things get interesting. Like this recipe for “Frank’s Absolutely Favorite Drink”, the “Flame of Love” from some guy named Pepe Ruiz who tended the bar at Chasen’s in LA. I doubt Frank would have sat still while Pepe swirled, torched, chilled and squeezed this concoction. Warning: this seems to be part of a greater work of fiction…perhaps.

Frank was a particular drinker, but a typical one in the ’50s, preferring only the merest splash of vermouth. As HuffPo blogger Tony Sachs wrote: “Put more than a whisper of vermouth in your martini and you were looked upon as a freak or possibly a commie.” I doubt he fancied that “Dry Manhattan” recipe very much at all.

So what did he like?

Frank’s term for all hard liquor was “gasoline”, but he applied that moniker most frequently to his favorite amber elixir; that it was his favorite seems in little doubt:

“Jack Daniel’s whisky was Sinatra’s signature drink, and he would rarely be seen for long without a tumbler in his hand. The Washington Post even went so far as to nickname him ‘The Bourbon Baritone’… The signal for party-time at Twin Palms came when Sinatra hoisted a flag bearing the Jack Daniel’s logo above the mansion. It was perhaps fitting, then, that Sinatra was buried in 1998 with a bottle of JD slipped into his coat pocket.”

Back again to the Savoy in London, we get a confirmation:

“‘Always Jack Daniel’s on ice,’ Gower says. Frank loved Jack and Jack loved Frank. Their union lasted longer than most marriages, Frank’s included – over 50 years in total..”

This habit was carried over to his performing persona as well. This from a nice article by his last tour manager, Hank Cattaneo:

“(Sinatra said) “What time do we go on, Hank?” Whatever time was stamped on the ticket, was when we went on. Knowing well his requirements that the show start on-time, I always cued the overture a minute early. I knew he would look at his watch when he heard the downbeat. (…H)e never sat while waiting to go on. His tuxedo was not to acquire any new creases. A cherry Life-saver, then a check of his pocket for that single cigarette and lighter. He would have these on stage with his signature drink of Jack Daniels.”

Sinatra’s daughters Tina and Nancy are also on the record that his drink of choice was the fine Tennessee whiskey. Tina said in an interview:
“…Frank’s drink of choice was “Daniels” [sic] on ice. Not Jack like you might be calling it. Nope. It’s Daniels. Over ice.”

This great video clip of Tina speaking about her father’s favorite cocktail, courtesy of the fine fellows at “Drinking Made Easy” confirms the “Daniel’s” story; and, as a bonus, one of the DME guys chugs a glass of “Daniel’s…rocks” on camera. It’s pretty awesome, but Frank would not have approved. His “Daniel’s, rocks” was a “gentleman’s drink”, and to enjoy it, one had to “…sip it with some class. You’re a man not a G-D DAMN FRAT BOY”.

I also found a “quote” from Nancy via some guy she supposedly tweeted (though he didn’t provide a link to the actual tweet, and much of the blog post seem a bit far-fetched). which at least provides greater detail into exactly how Frank liked to drink his Daniels:
“… a tweet from the daughter and retro icon herself, Nancy Sinatra informed me that he had “Jack Daniels, with water and 3 ice cubes”.

OK, so now we actually have a drink recipe…but of course, it’s not that simple…there are many variations on the theme. Nancy maybe says 3 cubes; some folks say more:

“And for Ol’ Blue Eyes, the cocktail of choice was a mix of four ice cubes, two fingers of Jack Daniel’s whiskey, and a splash of water.”

And of course, you’re no Goddammned Frat Boy, so you have to drink it correctly:

“…if you want to hold the drink like Frank, don’t touch the rim. Cup it in your hand, insulated by a cocktail napkin.”

Now one might ask: why would a great and powerful man like Frank Sinatra go with something as pedestrian as Jack Daniel’s? Surely, he could have afforded the finest Scotch, the best bourbon…what was the appeal of Jack…er, Daniel’s? Tony Sachs has the explanation:

“…you have to remember that the era in which he came of age was as different a time for booze as it was for pop music. Single malts were literally unheard of outside Scotland. Rye was in the midst of a decades-long death spiral. Small-batch and single barrel bourbons were still decades in the future. … The hot new spirit was… vodka.

And Jack Daniel’s wasn’t Jack Daniel’s, the best-selling whiskey in the world. It was a relatively obscure “sour mash” whiskey, made in small quantities and sold until the mid-1950s by word of mouth rather than advertising. Sinatra himself, the story goes, was introduced to it by Jackie Gleason at Toots Shor’s legendary saloon in Manhattan. Jack Daniel’s was the craft spirit of its day, and drinking it was a mark of distinction rather than conformity.”

So there you have it. Sinatra drank Daniel’s because it was a rare bird, not just hi-test gasoline but a very special mixture. He was very particular about how it was served to him and how he consumed it, as befits a man who considers that he has class, substance and style. I will unequivocally agree, even though he’s not my favorite performer from not my favorite era of pop music. Hey, Daniel’s isn’t my favorite whiskey, either, although it’ll do in a pinch.

Sinatra’s public persona was that of a man with an immense amount of “cool”, a paragon of style, class and taste (as those qualities were rather rigidly defined in the 50s and early 60s). In an era which prized conformity, his drinking habits conformed with what most folks would call “normal”:

“Wine was fine with dinner, beer was great for watching a baseball game, but it was hard liquor that powered (Sinatra). Jack rocks (Frank called it gasoline) was the primary fuel, supplemented with dry martinis and scotch.

Its nice to know that you and I can share in at least a little of his routine, anytime we care to, by re-creating his simple signature drink. The webbots over at eHow did a very nice job of creating a slide show which will show you in detail how to do just that:

And if you’re a Sinatra completist, the Jack Daniel’s marketing department (the same guys who made Jack the most popular whiskey in the world) has created just the product for you – a “Sinatra Select” blend, theoretically from hand-selected single barrels blended with some of the standard “Old No. 7”, and labeled with a “distinct ‘hat‘ logo”. You’ll pay a lot for that logo, I’m sure. Tony Sachs thinks it’s worth the dough:

“Sinatra Select is a much denser and chewier concoction than Old No. 7, rich with caramel, oak, candied orange peel and a fair amount of spice. I enjoy it best neat, but it also makes for a luscious Manhattan or Old Fashioned.”

So there ya have it…happy birthday Mr. S! Here’s lookin’ at you.

Until next time…have another one, I’m buyin’…


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