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Jack and Frank: A Friendship for the ages

Mike October 2, 2021

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The year was 1947. Frank Sinatra (1915-1998) was sitting in a smoky New York City bar, just about to order a drink. It was at this point that his company for the evening, entertainer Jackie Gleason, made a drink suggestion that Frank would not soon forget: “Jack Daniel’s. That’s a good place to start.”

In 2013, Jack Daniel’s sold more than 11 million cases of the company’s iconic Black Label Tennessee Whiskey bottle. According to the company’s historian, Nelson Eddy, that would never have been possible if not for Frank Sinatra.

“Frank’s introduced to Jack Daniel’s in around 1947, we’re a brand that’s under 200,000 cases per year at that point, very small brand,” Eddy says. “And the only reason Sinatra finds out about it, he’s at a bar with Jackie Gleason. Gleason turns to him and says, ‘Have you tried Jack Daniel’s?’ He tries it that night, he falls in love with it, he feels like he’s discovered it and given the number of cases that were out there, in a way, he did discover it for many, many people. He starts calling it, from the stage, the nectar of the gods and the best booze in the world.”

Few could’ve predicted the lifelong friendship between Frank & Jack that would follow. Frank was no stranger to love and loss, but when it came to Old No. 7, his affection was unflinching. Wherever Frank went, Jack was nearby. At the base of his mic stand on-stage. Aboard his private jet. Front row at award ceremonies. Even in his jacket pocket when he was laid to rest.

Jack Daniel’s marked the run-up to the centenary of Frank Sinatra’s birth with the launch of Jack Daniel’s Sinatra Select – a new luxury expression initially only available in travel retail.

Bottled at 45% abv, Sinatra Select is matured for longer than the core Jack Daniel’s bottling and made using whiskey matured in “Sinatra barrels” – which have carved grooves on their interior to expose the spirit to more wood.

Sinatra would typically offer a toast using a glass of Jack Daniel’s during his concerts from the 1950s to the 1990s. “I can assure you he was very fond of Jack Daniel’s for many years,” said his son, Frank Sinatra Jr, at the global launch in Cannes.

The technique, used for the first time as the main component of a Jack Daniel’s blend, results in a faster-maturing whiskey with more noticeable spicy and smoky flavours and a richer character.

Sinatra Select was released with an initial suggested retail price of $150, launching in Las Vegas Airport in December, chosen because of Sinatra’s historical association with the city. It was then be rolled out to multiple airport locations around the world, targeting about 200 airports in total.

The whiskey is packaged in a one-litre bottle with gift box and book, with the interior of the gift box mirroring the grooves on the inside of the barrels. Orange is used as a highlight as a salute to Sinatra’s love of what he called the “happiest” colour.

“The year 2015 was Frank Sinatra’s 100th birthday. Over the next couple of years, we’ll be building up to that moment,” he added. The technique, used for the first time as the main component of a Jack Daniel’s blend, results in a faster-maturing whiskey with more noticeable spicy and smoky flavours and a richer character.

Sinatra Select was released with an initial suggested retail price of $150, launching in Las Vegas Airport in December, chosen because of Sinatra’s historical association with the city. It was then be rolled out to multiple airport locations around the world, targeting about 200 airports in total.

The whiskey is packaged in a one-litre bottle with gift box and book, with the interior of the gift box mirroring the grooves on the inside of the barrels. Orange is used as a highlight as a salute to Sinatra’s love of what he called the “happiest” colour.

“The year 2015 was Frank Sinatra’s 100th birthday. Over the next couple of years, we’ll be building up to that moment,” he added.

Sinatra Select was the first ever global launch for a Jack Daniel’s product, and the first time the distiller launched any product or any brand in multiple markets at the same time.

Tasting Notes: Jack Daniel’s Sinatra Select

Vital stats: 90 proof; mash bill of 80% corn, 8% rye, 12% malted barley; about $120-180 depending on where you find it (it can be hard to find)

Appearance: Pretty in the bottle: a rich, deep, backlit orange amber. In the glass, a little flatter: khaki color but not khakis, at least not pleated ones.

Nose: Very strong, very sweet, very fruity. This whiskey does not croon. It shouts! What does it shout? “I am fruit! It is fall, and I am honeycrisp apple! Also: mango!” There is—and this is not necessarily a detraction—a hint of…envelope glue. (But not the Seinfeld kind. I hope.)

Palate: On initial sip, this is crackly. It finishes a bit unfinished. Compared to Jack Daniel’s Straight Rye, this rides roughshod. I added a couple of drops of water to it, which smoothed things a touch but also took away any nascent richness. But also like the rye I tried, it becomes less harsh if it sits a while. Maybe it wears you down?

Don’t call it Bourbon!

Jack Daniel’s is not a Bourbon. In fact, the federal government granted it the title of Tennessee Whiskey in 1941, some 80 years after Jack started his business. What differentiates it from Bourbon is the filtration process, the “Lincoln County Process”, which involves filtering the spirit through a 10-foot-thick layer of maple charcoal before barrel aging.

The Distillery has had only 9 Master Distillers

Jack Daniel’s is the oldest registered distillery in the U.S. Since 1866, the Jack Daniel’s Distillery has had only 9 Master Distillers, a figure who oversees the entire whiskey production process. The first was Nathan “Nearest” Green, until 1881, while the last, since 2020, is Chris Fletcher.

No. 1 Nearest Green 1866 to 1881
No. 2 Jasper Newton “Jack” Daniel 1881 to 1911
No. 3 Jess Motlow 1911 to 1941
No. 4 Lem Tolley 1941 to 1963
No. 5 Jess Gamble 1964 to 1966
No. 6 Frank Bobo 1966 to 1988
No. 7 Jimmy Bedford 1988 to 2007
No. 8 Jeff Arnett 2008 to 2020
No. 9 Chris Fletcher 2020 to ?

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