The Only Way Frank Sinatra Drank His Favorite Whiskey, Jack Daniel's

Frank Sinatra was a famous fan of the Rusty Nail – a two-parter cocktail made from Scotch and Drambuie. But, for Ol' Blue Eyes, it wasn't just about liking whiskey. Sinatra was a Jack Daniel's superfan, and his passionate fandom brought the rest of America along for the ride — a ride that is still running.

Jack Daniel's sipped "Sinatra-style" is a two-finger pour of whiskey with three ice cubes and a splash of water in a rocks glass. Per the lore, it all started when Sinatra rolled into an unnamed New York City bar one night in 1947 to hang out with fellow entertainer Jackie Gleason. When Sinatra sat down to order, he told Gleason that he wanted a "serious" drink, to which his companion allegedly suggested, "Jack Daniel's. That's a good place to start," per the Jack Daniel's website.

At the time, Sinatra was already a household name. The singer's best-known work was still to come in the 1950s after he joined Nelson Riddle at Capitol Records, but 1947 was the same year that he starred in the iconic musical "It Happened in Brooklyn." The distillery, on the other hand, still had a long way to travel on the craggy road to stardom. In 1947, Jack Daniel's (which is now the oldest registered distillery in America), was selling less than 200,000 cases per year. In no time at all, the proto-brand ambassador transformed the company into a pop culture icon, and the rest is (literally) history.

Jack Daniel's salesman Angelo Lucchesi quickly became a friend of Sinatra's. The singer was known to hoist a Jack Daniel's flag over his Palm Springs residence to let neighbors know when a cocktail hour had begun. He had a blazer embroidered with the words "Jack Daniel's Country Club" and gave matching jackets to his closest friends. In 1955, Sinatra reportedly came on stage holding a glass of Jack on the Rocks and announced to the audience: "Ladies and gentlemen, this is Jack Daniel's, and it's the nectar of the gods." 

From then on, a bottle of Old No. 7 could be spied onstage with Ol' Blue Eyes, sitting at the base of his mic stand. According to Bill Zehme, who wrote, "The Way You Wear Your Hat: Frank Sinatra and the Lost Art of Livin'," one time when Sinatra was visiting the Four Seasons in Boston, he plunged in his hand and picked out all but a few cubes in his ice-filled Jack on the rocks. As the story goes, the bartender asked, "'Is there a problem, Mr Sinatra?' Quietly, he explained: 'No, but with all this ice, I figured we're supposed to go skating here or something. That's not my sport,'" via Scotch Whiskey Magazine. When he passed away in 1998, among the items with which Sinatra was buried included a roll of dimes to call his friends with, a pack of Camels, and a bottle of Jack.

The enduring legacy of Frank Sinatra's connection with Jack Daniel's didn't stop there. In 2015, in honor of what would have been his 100th birthday, the brand released Frank Sinatra Century, a Tennessee whiskey. The limited-edition run was crafted by Master Distiller Jeff Arnett and contained 100 barrels of ultra-premium whiskey bottled at 100-proof, for $499 per liter.

The brand's permanent "Sinatra Select" line debuted in 2012. As the website puts it, Sinatra Select is a bottle that "pays tribute to Jack's biggest fan," made in unique "Sinatra barrels" with extra deep grooves for a bigger toasted oak flavor and an accessible vanilla finish. It's described as being "Smooth as Sinatra," yet totes a 45% ABV — higher than JD's flagship Black Label whiskey and the same 90-proof strength that Old No. 7 would have had when Sinatra first tried it in the 1940s. (Jack Daniel's lowered Old No. 7 from 90-proof to 86-proof in 1987, then reduced it again to 80-proof in 2002).

At around $169.99 per bottle, it's a notably high price for a whiskey without an age statement, but since Sinatra made it so fashionable, fans are also paying for the Jack Daniel's name. Today, the distillery continues its connection to the music scene with rockers like Keith Richards, Jimmy Page, Mick Jagger, Tom Petty, and Bruce Springsteen having been photographed drinking Old No 7. In 2013 alone, Jack Daniel's sold over 11 million cases of Black Label.