Frank Sinatra. The Chairman. Frank & Ava & Mia & Barbara. Jack Daniel’s. Old No. 7. Jack & Ginger & Coke & Rocks & Lemonade.


by Michael Cecconi

Who made the 20th century? On the booze front you have the shadow of Prohibition looming, the rise of vodka, the rise and fall and rise again of proper cocktails, and through it all you have Jack Daniel’s. In entertainment you have the death of silent films and the rise of the talkie, the exuberant music of the ’20s falling to the repression of the ’50s leading to the counterculture of the ’60s wigging out to disco in the ’70s to the big hair groups of the ’80s, and through it all you had Frank Sinatra.

Certain things are of their time and yet can transcend their temporal moorings and achieve a state of grace. These two mammoths do that. Jack Daniel’s has been in production more or less since 1875. While Sinatra forever went out of production in 1998. We have the catbird seat here in the 21st century: we have at our fingertips all of Sinatra’s output (though we will never get the rush of seeing a live show) and Jack Daniel’s whiskey is available, quite literally, wherever spirits are sold (but any boozehound worth their salt would pay dearly to taste what those first bottles in the 1800s had in them).

Their legacies live on … in every bottle and in both music and film for Frank. The bottles used to be filled at a perfect-for-mixology 90 proof. As a general rule of thumb, the higher the proof of a spirit the more concentrated the flavor, and the sturdier it is as a foundation for a cocktail. The new Sinatra Select expression of Jack Daniel’s reclaims its spirit, literally, by returning to 90 proof. And while there are any number of reasons to lower the proof (taxes, changing tastes, bottom lines), it is good to have an opportunity to taste a bit of Jack Daniel’s the way the Chairman enjoyed it.

Sinatra’s legacy evolved, as well. In his heyday, with his intensity and commitment, he was a force of nature to behold. From the serious (The Manchurian Candidate) to the coolly comedic (Ocean’s 11), from Broadway spectacle (On the Town) to farce (Come Blow Your Horn) he was able to inhabit a role and yet inevitably still express the charisma of the performer. He basically acted his way through singing, too. His was a voice that drink and smoke only made better* (see also: Bono**). In the ’90s his swan song was two albums worth of “duets.” The vocals were recorded separately, matched in the studio, and went on to become some of Frank’s best selling records. It seems that all the heavy lifting Frank and Jack did throughout the 1900s cemented their reputations and no question of proof or of quality was going to change it.


So let us raise a toast (preferably Jack on the rocks with a cocktail napkin wrapped under the base to protect the hand) to these two epics—especially when they were in their prime. For the whiskey that was strong enough to weather the hostile landscape of Prohibition, and for a talent that would not rest, an intensity and charm onscreen that belongs in the pantheon of great actors, and a way to tell a story with a song that remains as potent today as it was 60 years ago.

ChairmanoftheNightChairman of the Night

  • Rocks glass
  • 2 oz Jack Daniel’s
  • 1/2 oz maple simple syrup***
  • 2 dashes Fees Orange Bitters
  • 4 dashes Angostura Bitters

Combine whiskey, maple, orange and Angostura, and ice in a tin. Shake and strain into rocks glass, then add fresh ice.

***Maple simple syrup: 2 parts maple syrup to 1 part hot water. Stir to combine.Horizontal Rule*“Drinking Again” sung by Mr. S  is a 1962 torch song with lyrics by Johnny Mercer and music by Doris Tauber. Listen here.

**In the last paragraph of this interview, Bono says drink and smoking were part of his voice change. Horizontal RuleThis week, Jack Daniels presents Ring-a-Ding Ding: The Films of Frank Sinatra festivities at the Vogue Theatre in San Francisco. Here is a special deal for Sinatra fans: Buy a $10.50 ticket to opening night film – the rockin’ Ocean’s Eleven – and the party beforehand is on Frank. The festivities kick off at 5:30 p.m. on Friday August 21 at the Vogue theater when Festival Presenter Jack Daniel’s hosts a pop-up whiskey bar pouring Frank’s own premium label. It will be accompanied by savory snacks. By that time you should be in the mood to watch an 11-man team (comprised of Sinatra’s Rat Pack buddies) blow up Las Vegas. Now that is what we call “Ring-a-Ding-Ding!”

A special “All Festival Pass” is available for only $35.

For the complete schedule and advance ticket information visit the website.

Read more: Eat My Shorts features Frank Sinatra’s The House I Live In, Eat Like the Stars presents three of Frank Sinatra’s recipes, and a fan’s remembrance of meeting Old Blue Eyes.Horizontal RuleMichaelCecconiMichael likes all things drink-related. Michael likes movies. And, in an odd twist of fate, Michael loves words about movies. These three facts combine to make a perfect storm of sensibility, ability, and inebriation needed to fulfill duties at EatDrinkFilms. When not rhapsodizing about film, Michael tends the bar at Two Sisters Bar and Books in San Francisco. He teaches mixology in San Francisco and New York. And lately, he’s been trying to capture the magic of what he does in a bottle so he can spread his tasty libations across the land. Please feel free to contact him at with all queries.

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