The Love Song of Frank and Jack: How Sinatra Put Jack Daniel’s on the Map

Black and white archival photo of Frank Sinatra in the recording studio

In 1955, Jack Daniel’s wasn’t the liquor powerhouse we think of today, ubiquitous on bar shelves, the best-selling whiskey in the world. Though the distillery was nearly 100 years old, the Lynchburg company was still a small, regional brand, moving roughly 150,000 cases annually of its black-labeled Tennessee whiskey. By the end of 1956, however, that figure had doubled, and a shortage was taking root that would delay the export of Jack Daniel’s for almost two decades. What changed? The company received an endorsement from one very powerful friend.

That friend was Frank Sinatra, a dedicated whiskey drinker who took his Jack on three rocks with two fingers and just a splash of water. As Jack Daniel’s Master Distiller Jeff Arnett recounts, 1955 was the year that Sinatra brought a rocks glass onstage with him and uttered this magical line: “Ladies and gentlemen, this is Jack Daniel’s, and it’s the nectar of the gods.”

While the title didn’t exist as we now know it, Sinatra was, in a manner of thinking, Jack Daniel’s first brand ambassador. Without a contract or paycheck or any official partnership, Ol’ Blue Eyes had a measurable impact on his whiskey of choice simply by being the coolest guy in any room and telling his fans what he liked to drink.

“[Sinatra] literally took Jack Daniel’s from being a small, regional brand to being a household name — made us a pop-culture icon in a way,” says Arnett.

In exchange, Jack Daniel’s made sure his glass was never empty. Angelo Lucchesi, the brand’s first salesman, was charged with keeping the singer stocked with his favorite sauce, which was in allocation at the time. Salesman Danny Campo, who worked for Jack Daniel’s for 29 years, remembers getting calls from Lucchesi, asking him to deliver a case to this club or that one. “If Frank Sinatra was in town, you made sure a case of Jack was in his dressing room.”

Fifteen years after the Rat Pack captain died in 1998 (and was buried with his beloved black label), Jack Daniel’s did one better: It created a special whiskey dedicated to the legendary entertainer. Sinatra Select debuted in 2013, and this year, Arnett has followed it with Sinatra Century, a limited release to celebrate the singer’s 100th birthday on December 12.

In the 1950s, Arnett explains, whiskeys were generally darker and oakier with more intense, woody finishes. When Sinatra started drinking Jack Daniel’s in 1947 — legend has it thanks to a tip from comedian Jackie Gleason — he was probably sipping a bigger and beefier iteration of the company’s classic Old No. 7.

With that idea in mind, Arnett set out to make a whiskey in the style of vintage Jack Daniel’s. “The words that come to mind are ‘bold’ and ‘smooth.’ That’s who Frank was as a person, and that’s what the whiskey should be.”

To achieve the ideal flavor, the company carved grooves into its Sinatra barrels, doubling the ratio of wood to whiskey and leaving the extra pieces inside each barrel to marinate in the spirit, giving it a deeper, oakier tone. The result was Sinatra Select, a 90-proof whiskey with a wood-intense flavor and a strong finish, just as Sinatra would have liked it.

“We had not, as a brand, been someone who’d put many names on our bottles,” Arnett says. “Frank was the first person who was not a Jack Daniel’s relative or employee who had his own bottle.”

Now, he has two. To mark the Chairman of the Board’s 100th birthday on December 12, the master distiller collaborated with the Sinatra clan to create Sinatra Century, released in October. The concept is simple: “100 barrels at 100 proof for his 100th birthday.”

Arnett made three batches at varying levels of bold and flew to LA to meet with the Sinatras. Sitting around the kitchen table, they tasted the various whiskeys together. The one the family selected? “It was the one we thought was the most interesting,” Arnett recalls, “the highest level of the Sinatra barrel in it, biggest and the boldest.”

Stored in a sleek blue case, just under 20,000 numbered bottles of Sinatra Century have been released, with half of that total being distributed in the U.S. The collector’s package, which retails for $499, includes a small book about the man and the booze, and a USB-stick replica of Sinatra’s tie clip, containing a never-before-released recording from the Sinatra family archives, a full concert taped at the Sands Casino in Las Vegas in 1966.

Arnett likes to think that Frank would be smiling about it, “telling everyone that he had a whiskey with his name on it and showing it to everyone.”

And if you want to raise a glass for the singer’s birthday that’s faithful to what Sinatra himself called the “nectar of the gods,” the master distiller suggests pouring Jack Daniel’s Sinatra Select as Frank would have — three rocks, two fingers, splash of water.

“I definitely think that would have spoken to Frank and his era. It would’ve been very close to what he held up on stage that night.”