Frankie Goes To Lynchburg: In Praise Of Jack Daniel's Sinatra Select

The Chairman of the Board with his favorite whiskey — and one of his favorite people by his side.

In today's enlightened age of spirits and cocktails, it's weird to think that Frank Sinatra's favorite drink was Jack Daniel's on the rocks with water. I mean, the guy had been around the world a few times, both literally and figuratively. He must have had the opportunity to try anything and everything. The rarest single malt Scotches. The finest ryes. The most exclusive bourbons. The best small-batch, single barrel, limited edition, sherry cask-matured what-have-you was undoubtedly his for the tasting. And he chose watered-down JD? With ice to water it down even more?

But before you start going around declaring Sinatra to be a more interesting singer than a drinker, as I used to do, you have to remember that the era in which he became JD’s unofficial spokesman 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. Put more than a whisper of vermouth in your martini and you were looked upon as a freak or possibly a commie. 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 (it’s technically a bourbon, but the brand chooses not to put itself under that umbrella), 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.

I discovered both Frank and Jack around the same time, during my high school days. I was a little premature for both. Too young to really comprehend the heady subjects of love, loss and longing that Sinatra sang about, and certainly too young to legally drink anything alcoholic, including Jack Daniel's. By then, JD had lowered its alcoholic content from 90 proof down to 86, and Ol' Blue Eyes ... well, he was in his seventies by then, and a little less high-octane himself. But I found them both life-affirming in their own way, and both became a regular part of my diet. Sometimes it seems like I spent my 20s listening to Frank Sinatra and drinking Jack Daniel's — not necessarily in that order.

Sinatra didn't live to experience the cocktail renaissance that slowly gathered steam during the '90s and exploded in the new millennium. He was a man as loyal to his whiskey as he was to his friends, so chances are he would have stuck with Old No. 7 and eschewed Knob Creek and New Riff and High West and all the other new brands that redefined what American whiskey could and should be in the 21st century. (Although I like to think that he'd have enjoyed Jack Daniel's own excellent Single Barrel expression, which launched a year or so before he died in 1998.)

I, on the other hand, wasn't so loyal. When booze connoisseurs raved about the new brands that started popping up in bars and liquor stores seemingly on a weekly basis, how could I possibly stick with the tried and true?

Truth be told, I felt betrayed as well. In 2004, Jack Daniel's once again lowered the alcohol content of its flagship Old No. 7 expression, from 43 percent proof to 40 percent — supposedly at the behest of its customers, who preferred a lower-proof spirit. I was so indignant that I wrote a letter of protest to the company. How could they mess with such a legendary whiskey? I trotted out the well-worn "painting a mustache on the Mona Lisa" cliché, insinuated that Sinatra himself was no doubt rolling in his grave at such a travesty, and declared a one-man boycott of Jack Daniel's and its new, wimpier Tennessee Sipping Whiskey. Michter's, Booker's, Wild Turkey, and JD’s Tennessee rival George Dickel, among countless other brands, helped me feel like I didn't need Jack in my life anymore. Heaven knows Jack Daniel's didn't need me. It was and still is the mighty colossus, the undisputed champion — the Frank Sinatra, if you will — of whiskey, with sales that stand head and shoulders above every other brand in the world.

But almost a decade later, there appeared a new chapter in the love story of Frank and Jack, one which pulled me back into the fold.  Sinatra Select is packaged in a stunning black and orange box (orange was FS’ favorite color) with a special Cavanaugh hat logo, with a short book inside (uncredited, but I suspect it's written by the great writer and Rat Pack-ologist Bill Zehme) testifying to the long Sinatra-Daniel's romance, and a generous one-liter bottle of a specially crafted whiskey inspired by Frank himself.

Of course, pretty packaging doesn't make a great spirit any more than putting on a suit and singing standards turns Michael Bublé into Frank Sinatra. To their credit, the JD team, led by distiller Jeff Arnett, put in the effort. Sinatra Select is aged in specially selected "Sinatra barrels," which have grooves cut into the interior after the wood is charred, putting the whiskey in contact with wood that has been toasted but not charred as deeply. It's also aged somewhat longer (I've heard it's about a year) than standard Old No. 7, in a prime spot in the Daniel's warehouse. It's then bottled at a healthy 90 proof. The final product is closer to Jack Daniel's as it was when Frankie started drinking it, which should please Sinatra fans, whiskey connoisseurs and retrophiles alike.

I took my first sip with some trepidation. I really didn't want Jack Daniel's to screw this up. The greatest singer of the 20th century (I will brook no dissenting opinions here, sorry) deserves a great whiskey. And fortunately, they delivered. 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. As Sinatra himself was known to say, "This is a gentleman's drink." In the interest of Sinatralogical research, I even tried it His Way -- with the ice and water. Sinatra Select's flavor is big enough to stand up to all that dilution, even if it's not the ideal way to drink it in this whiskey lover's opinion.

Jack Daniel’s took their Sinatra connection to the next level in 2015 with the limited edition Sinatra Century, a 100-proof beauty which commemorated Ol’ Blue Eyes’ 100th birthday. It too was terrific, but it cost $500 at the time, and I’m guessing the price has gone up still further since then, if you can even find it. Enjoy it if you’ve got it, but if you’re looking for the best liquid accompaniment to Songs For Swingin’ Lovers or September Of My Years, Sinatra Select (itself a hefty $160 or so) is all you need.