Sinatra Edition Jack Daniels Is the Second-Best Sinatra Novelty

The other is an ‘81 Chrysler Imperial with paint matched to the Chairman’s irises.

Spirits manufacturer Jack Daniels has dug up Frank Sinatra’s eroded, velour-encased corpse and is parading it through the nation’s duty free stores, all in the name of higher quarterly profits. (At least, metaphorically.) This is Jack Daniel’s Sinatra Century, a commemorative, 100-proof answer to the question, what to get the Dead Crooner Who Has Everything? One hundred years ago, Frank Sinatra was born; today, we toast his life with limited-run, middle-quality booze available, in its manufacturer’s words, “in select duty free airport stores around the world.” Salud, harried travelers of Minneapolis-St. Paul International.

As with any aspirational spirit, there’s much poetry in the distilling process of Jack Daniel’s Sinatra Century 100 Proof Tennessee Whiskey. The barrels are “distinctively crafted,” with “interior grooves” that “coax the whiskey to greater depths.” If Frank were still around, he could show that barrel a thing or two about an interior groove. And those eyes, those famous blues, held nothing if not great depths. Is Jack Daniels trying to tell us they infused distilling barrels with Frank Sinatra’s essence, siphoned from a mausoleum in Cathedral City? Inconclusive.

Still, even with those anthropomorphic barrels, Jack Daniels Sinatra Century is only the second best Sinatra-branded American product of our times. The first? The 1981 Chrysler Imperial Frank Sinatra. In 1981, Chrysler’s royal lance meant to pierce the American luxury market, was selling poorly. The Imperial’s “economy-minded” 318 cubic-inch V8 was neither economical or fast; its novel fuel-injection system failed almost 100% of the time; it drove, for all its trimmings, like a Cordoba. In order to stimulate the sales of a car almost no one loved, CEO Lee Iacocca asked a favor of his universally-beloved pal, Frank Sinatra. Can I name America’s fourth best luxury car in your honor? After a presumable several tumblers, Sinatra agreed.

Jack Daniels

With legal squared away, Chrysler released the Imperial “FS,” with “Blues Eyes” paint, sky-blue leather, Sinatra emblems and ten (!) Frank Sinatra cassettes. Two-hundred and seventy-eight hardcore fans special-ordered the Sinatra edition Imperial, paying a staggering $2000 ($5,200+ today) over the standard car. That’s a stunning number of cars, considering how widely available Sinatra cassettes were at the time.


A businessman of the first degree, Frank loved the old Chrysler. Maybe Frank would be proud of this commemorative whiskey. So proud, he’d demand a cut. And then send in the mob for a second cut.

Happy Birthday, Frank.