Ed. note: Jack Daniel’s produced a limited-batch sour-mash whiskey called “Sinatra Century” to mark the singer’s 100th birthday, December 12, 2015. Lehman’s book Sinatra’s Century: One Hundred Notes on the Man and His World was published by HarperCollins at the same time. An editor at The Wall Street Journal noted the coincidence and commissioned Lehman, who likes good bourbon, to review the new whiskey, which came in a gift box including a thumb drive containing the recording of a Sinatra show at the Sands Hotel in Las Vegas in January 1966.
1. The Background
Frank Sinatra discovered Jack Daniel’s one sleepless night in the early 1940s. “It’s been the oil to my engine ever since,” he later said. He famously praised “anything that gets you through the night, be it prayer, tranquilizers or Jack Daniel’s.” Frank always kept a bottle nearby, offstage, and he was buried with a flask of JD in his casket.
In her autobiography, Judith Campbell Exner —the moll who was mistress to both John F. Kennedy and the head of the Chicago mob—recalled a day spent with Sinatra. He “acknowledged the comings and goings of an endless string of visitors, growled at flunkies, drank martinis, ate lunch, drank Jack Daniel’s, ate hors d’oeuvres, drank Jack Daniel’s, ate dinner, and drank more Jack Daniel’s.”
By the mid-1960s, Sinatra could drink a fifth of Jack Daniel’s and still go on stage.
2) The Anticipation
Like any respectable Sinatra aficionado, I have imbibed my share of Tennessee’s trademark sour mash whiskey. And as the author of a new book on Sinatra, I had an extra incentive to try the latest ultra-premium Jack Daniel’s bottle sent to me by my editor at The Wall Street Journal: a limited-edition 100-proof whiskey aged in 100 “alligator-charred” oak barrels (so called for the scaly interior surface left by the fire, the deepest of all the chars whiskey producers use to impart flavor and color to the liquor). It hit shelves in October—in plenty of time for toasts to Frank Sinatra on his 100th birthday, December 12, 2015.
The whiskey is called Sinatra Century. By serendipitous coincidence, my new book is called “Sinatra’s Century.” I wrote it, quite simply, because I have loved the singer’s voice, his musical savvy, his definitive versions of great standards ever since I heard “All the Way” and “Witchcraft” on the radio when I was eight or nine and grasped the essence of swing from Sinatra albums a few years later. Timing it to coincide with the centennial, I wrote the book in 100 parts, because Sinatra’s career exists in exquisite counterpoint with what Henry Luce called the “American century” and because the century is the perfect form for a subject with so many facets.
Jack Daniel’s already has a top-shelf whiskey with Sinatra’s name on it – 90 proof Sinatra Select, which is selling well, at twice the price of single-barrel bourbons that are just as good. So there was a part of me that wondered whether the same would be true with “Sinatra Century” – whether JD is selling a name, an event, and a future souvenir rather than a whiskey that can go head to head with A. H. Hirsch Reserve or the best of Buffalo Trace’s Antique Collection.
3) The Presentation
The presentation of Sinatra Century is as lavish as it should be, priced at $379 or more per one-liter bottle. It arrives in a deep blue-indigo lacquered carrying case with an engraved brass handle on top. Pop open the case, and the bottle sits in a custom groove, like a dark liquid jewel set against black velvet. Each bottle is numbered—mine is FAS 23095, the initials standing for Francis Albert Sinatra. Also in their own made-to-size grooves are a hardbound booklet devoted to Sinatra’s relationship with Jack Daniel’s and a tie clip that doubles as a thumb drive.
That last item comes loaded with a previously unreleased album of a live Sinatra performance: thirteen songs, two monologues and a coda, all recorded at the Sands Hotel in Las Vegas in January 1966. Frank had just turned fifty and was teaming up with the brilliant arranger Quincy Jones backed by the Count Basie Orchestra, and what better way to return to that evening than with a rocks glass in hand?
4) The Proof
Isn’t “proof” a lovely word? It stands in one context for the potency of a potable, and in another it means verification: a geometrical proof, say, or the proof of the pudding. Both senses come into play here. Would Sinatra Century prove potent enough to provide the perfect accompaniment to belters like “Luck Be a Lady” and “Fly Me to the Moon”? At 100 proof, it had better. (The standard “Old No. 7” Jack Daniel’s bottle clocks in at a mere 80.)
As to color, I said amber, my wife said topaz. I said tongue of flame, my wife said Stradivarius. She described the taste as “warm orange afterglow.” I took another sip and said, “Cognac.” She sipped and said, “The Cognac of bourbons.” Goes well with dark chocolate. Warms the soul “in a drear-nighted December” (to quote Keats).
The whiskey is the best I’ve ever had from Jack Daniel’s.
How to drink it? Neat or with a few ice cubes. We stuck to Sinatra’s own recipe: “three rocks, two fingers, and a splash”–a Sinatra haiku, when you think about it. We omitted the splash.
5. The Playlist
Sinatra Century promises not merely a whiskey but an experience. So you’re sitting in your favorite reclining armchair sipping and playing the recording of that Sands appearance of January 1966. It opens with a trusty icebreaker, “Come Fly with Me,” then turns to a ballad he’s sung since his crooner days, the Gershwins’ “I’ve Got a Crush on You.” Self-consciousness spoils the verse intro. The skinny singer can scarcely keep a straight face when obliged to sing “I’m your big and brave and handsome Romeo.”
He’s on safer ground with Cole Porter’s “I’ve Got You Under My Skin.” Perhaps the most celebrated of all Sinatra’s up-tempo finger-snappers, it brings out his swinging best. In adapting Nelson Riddle’s 1956 arrangement, Quincy Jones makes miraculous use of reeds and muted horns to compensate for the lack of a string section.
Sinatra always maintained he was at heart a saloon singer and he proves it anew in “Street of Dreams” and Matt Dennis’s great, haunting “Angel Eyes.” As you savor another swallow, the pace changes with “Fly Me to the Moon,” a highlight of the night. Sinatra reinvented Bart Howard’s 1954 song: It wasn’t a sad wistful plea, after all, but an assertive proclamation of love. It was also a nod to NASA’s great decade, the conquest of space as a seduction song. Killer arrangement. Love that flute.
The timeless “You Make Me Feel So Young” shows Sinatra at his most buoyant, and then he turns up the warmth in Johnny Mandel’s Oscar-winning “Shadow of Your Smile.” Sinatra is dating Mia Farrow and Mia likes the song.
Frank Loesser’s “Luck Be a Lady” comes from the musical “Guys and Dolls.” In the movie version, Sinatra played Nathan Detroit, but it was Marlon Brando as Sky Masterson who got to sing this ode to gambling that marks the show’s heroic climax. Now, to correct the injustice, Sinatra demonstrates how the song should be sung. One of Sinatra’s anthems in the 1960s, a hymn to Las Vegas, here it’s as electric as “Fly Me to the Moon,” with a tail like that of “My Kind of Town.”
Time for another round.
The audience is hushed when Frank sings “It Was a Very Good Year,” where again the reeds do the work of strings, and then the Rodgers and Hart standard “Where or When,” not only a marvelous love song but also the greatest ever on the subject of déjà vu: “Some things that happen for the first time / Seem to be happening again.”
The nightclub act ends with a song Sinatra owns: “My Kind of Town,” the terrific tribute to Chicago that Sammy Cahn and Jimmy Van Heusen wrote for their boss to sing in “Robin and the Seven Hoods,” his last movie musical.
By now you’ve made a dent in the bottle and you’re robustly singing along.
— from “Author David Lehman Takes On Jack Daniel’s Sinatra Century,” in The Wall Street Journal, January 5, 2016
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