Friends for life: the story of Jack Daniel's and Frank Sinatra

On 20 July 1998, a sunny Los Angeles day like any other, at the Church of the Good Shepherd in Beverly Hills, Frank Sinatra’s funeral was attended by his family and Hollywood friends. Sinatra’s daughter Nancy slipped a mini-bottle of Jack Daniel’s, one of Frank’s most important mementos, into his blue suit. A pack of Camel cigarettes, a Zippo lighter, and a roll of ten dimes accompanied the whiskey into the singer’s afterlife.

Frank Sinatra’s close relationship with Jack Daniel’s was one of the greatest and most enduring relationships between a whiskey and an artist – probably between any celebrity and any brand. Sinatra was never the spokesman or hired hand for this whiskey. Had he been propositioned for payment, he would likely have dropped Jack like a hot potato; it was Jack’s distinctive flavour that made it his whiskey for 50 years. On stage, he would frequently announce, “Ladies and gentlemen, this is Jack Daniel’s, and it’s the nectar of the gods,” then pour a shot over ice and take a sip. How a rare, little Tennessee sippin’ whiskey developed such a close bond with a man Rolling Stone magazine declared “the 20th century’s greatest singer of popular song” is, ultimately, a story of familiarity and friendships.

Frank ‘met’ Jack through his friends, either at a post-dinner soirée with actor Humphrey Bogart or his other drinking buddy, entertainer Jackie Gleason, at Toots Shor’s, a famous saloon and restaurant on West 51st Street, New York. Toots Shor’s was where celebrities gathered to party, and Sinatra was a regular since the establishment opened in the early 1940s. Most nights, sports and Hollywood stars frequented Shor’s, including singer Bing Crosby, actor Charlie Chaplin, New York Yankees’ baseball star Joe DiMaggio, the aforementioned Bogart and Gleason, and other luminaries.

The most formidable character and friend of Sinatra was Gleason, who was known as ‘The Great One’. Gleason’s Dionysian drinking bouts at Toots Shor’s were of Olympian scale, matched by his imposing talent and personality. Around 1949, Shor’s began serving a novel backwoods Tennessee whiskey, an introduction that led Sinatra into a lifelong partnership.

Jack Daniel’s was a tiny brand back then. The distillery released Jack Daniel’s Black Label in December 1946, as a six-year-old whiskey, using stock made since Moore County had repealed its distilling ban in October 1938. This dry county in middle Tennessee is where Jack Daniel’s distillery manufactures its whiskey to this day. With limited inventory, Black Label sold less than 9,000 cases in 1948, targeting up-market venues in a handful of major cities in the South and Tri-State Area, focused on New York. By the end of 1950, Black Label was selling fewer than 20,000 cases, an infinitesimal figure compared to US domestic whiskey sales of 57 million cases.

Nevertheless, Jack began attracting America’s cultural producers and opinion leaders like rebel director-actors John Huston and Orson Welles, and gourmand Lucius Beebe. Promoted as being made using a unique process and billing itself as a ‘smoother, mellower whiskey’ crafted by an ‘expensive and an unhurried way of making whiskey’, Jack turned into a cult drink amongst America’s influential trendsetters.

In 1954, after suffering several years of setbacks, Sinatra’s fortunes rebounded. He won an Academy Award, new film and recording contracts, and a headlining act on the Las Vegas Strip. His shows featured bottles of Jack on stage, which he sipped during his show and continued drinking late into the night as he caroused with friends. Domiciled part of the time in Los Angeles in the 1950s, Bogart and Sinatra led a group of Hollywood A-listers known as the Holmby Hills Gang. One boozy night, Bogart’s wife, Lauren Bacall, said to them, “You look like a goddam ratpack.”

This informal drinking group often featured actors Errol Flynn, Elizabeth Taylor, Marylin Monroe, Judy Garland, Shirley McLean and Tracey Spencer, along with musician Nat King Cole and, of course, Jack Daniel’s whiskey. When Sinatra returned to his home in Palm Springs, his neighbours knew it was cocktail hour when the Jack Daniel’s flag was hoisted in his front yard.

When Sinatra teamed up with Dean Martin, Sammy Davis Jr (and Jack Daniel’s) in 1960, this growing gang of Vegas entertainers became the Rat Pack – the kings of cool. Where Frank and the Rat Pack went, Jack was there. In 1961, Sinatra bought a dual-prop Martin plane for $100,000 and fitted it out with a bar and piano for another $300,000. He named the plane El Dago, and stocked it with mini-bottles of El Dago–labelled Jack Daniel’s whiskey.

Performing at the Copacabana Club in New York in 1967, Sinatra could not secure supplies of Jack Daniel’s for his show and private use, as the brand was on strict allocation across America – a production bottleneck that continued until 1978. One of Sinatra’s management team mentioned this problem to Angelo Lucchesi, Jack Daniel’s first dedicated salesman, who was appointed in October 1953. Immediately, Lucchesi ensured Sinatra could sip on Jack before, during and after his shows.

So impressed was he with receiving the whiskey and distillery contact to access his favourite drink, Sinatra gave Lucchesi his private telephone numbers, so he was never without Jack. The singer and the salesman became fast friends, and it was probably Lucchesi who nominated Sinatra to become a Tennessee Squire (a member of an insider’s club for individuals who had proven to be a loyal friends of Jack Daniel’s whiskey). One of the benefits members received was a small plot of land in Lynchburg. Sinatra was chuffed at this privilege; he told everyone, including the media, that he owned an acre of land at the distillery. Unfortunately, the deed only gave members a one-square-inch plot. Frank got reallocated an acre.

When travelling overseas, Sinatra’s air cargo included cases of Jack. Arriving in London in 1962, Sinatra sported a blue blazer with a ‘JD Country Club’ pocket emblem, and, according to one newspaper report, the media ‘went into a tizzy guessing what royal household the crest represented’.

In October 2012, around 14 years after Frank Sinatra’s death, Jack Daniel’s Sinatra Select launched. Created in partnership with Frank Sinatra Enterprises, the company responsible for managing Sinatra’s assets and product licenses, the super-premium expression commemorates Sinatra’s unique relationship with Jack. Sinatra Select reflects the sensory style of Jack Daniel’s whiskey 60 years ago: at 45% ABV and more years in barrel, it’s slightly more oaky and spicier. Then, on Frank Sinatra’s 100th birthday, 12 December 2015, the commemorative Sinatra Century expression was released, made by mingling 100 barrels at 50% ABV (100 Proof). Sinatra Select now forms part of an expanding whiskey portfolio bearing the entertainer’s name.

A talented maverick, Sinatra also embodied machismo and danger. For people wanting to emulate his stylish, tough-guy image, he inspired the ‘brand-is-man’ industry, and Jack Daniel’s was the whiskey brand with which to be seen. In dozens of Hollywood movies, directors cast Jack as a supporting figure to straight-talking, heroic and idiosyncratic characters like Paul Newman in HUD (1963), Tom Cruise in A Few Good Men (1992), Al Pacino in Scent of a Woman (1992), and even Jack Nicholson in The Shining (1980). Jack Daniel’s was more than just a prop, representing characters’ inner strength.

Jack Daniel’s policy was not to pay for movie placement or endorsements, but everyone from bikers to rock artists sought pop-culture affinity with Jack’s rebel badge, including Keith Richards and the Rolling Stones, David Lee Roth of Van Halen and Amy Winehouse. It became standard practice for rock bands to have riders in their contracts to stock dressing rooms and hotel suites with Jack Daniel’s – even if they did not drink liquor. That’s star power with staying power.

Trust in others

Since the advent of whisky brand management, commercial partnerships have been a highly persuasive technique in gaining consumer trust, social proof and imbuing trademarks with an aura of humanity. The three most powerful and trusted sources in whisky’s promotional arsenal were royalty, then physicians and, today, celebrities.

Members of the British royal household can issue warrants, recognising ‘by appointment’ their purchasing approval of select goods and services. The imprimatur of royal warrants is similar to mega-influencers in today’s social media marketing: exceptional pulling power. The first whisky to come to the attention of the British royalty was Glenlivet (or, at least, a whisky from Glen Livet), when King George V visited Edinburgh in 1822. However, the first warrant granted was by King William IV to Brackla whisky in 1835, permitting the use of ‘Royal’ in the brand name. Queen Victoria followed in 1843, granting Chivas Brothers the use of Chivas Regal and later Royal Salute by Queen Elizabeth II in 1953. Other whisky makers awarded royal warrants are Dewar’s, Justerini & Brooks, Ballantine’s, Johnnie Walker, The Famous Grouse and Laphroaig (by the Prince of Wales in 1994).

Until the early 20th century, whisky was prescribed as medicine, with doctor testimonials bestowing professional gravitas and trust similar to royal titles. Spirits have been sold as cure-all, patent medicines since Dr Richard Stoughton’s Elixir received a British medicinal patent in 1712. After the introduction of the UK Medicinal Food Act (1812) and the US Revenue Act (1862), producers of alcoholic medicines enjoyed significant tax breaks, giving the industry a proverbial shot in the oral cavity. Bottles of whisky from quacks and doctors proliferated. The most notorious was Duffy’s Pure Malt Whiskey, a rectified rye. Walter Duffy created hundreds of fictitious doctors and paid quacks, and bribed a few physicians to make outlandish claims in newspaper advertisements. Other companies traded on the reputation of respected local doctors, such as Louisville surgeon Dr William S Forrester [sic], immortalised as Old Forester bourbon, a medicinal whiskey sold through Kentucky pharmacies from 1870.

The US Surgeon General assigned whiskey brands such as Old Taylor in 1880 as official suppliers of medicinal whiskey to the Army. In America, medicinal whiskey was reclassified as a drug in the pharmacological codex, despite most doctors prescribing medicinal liquor to the public throughout Prohibition, with over 64,000 doctors issued permits, and commanding over 40 million gallons of spirits. In the early 20th century, many countries enacted laws to prevent the dissemination of false therapeutic claims.

The age of mass media and mass marketing brought actors, sportspeople and musicians intimately into consumer lives. As whisky brands proliferated and marketers sought competitive advantages, celebrities were pressed into service. The greater their fame, the bigger the fee. The most active was Sean Connery, who leveraged his popular James Bond character: first with Jim Beam from 1966 to 1974, later fronting for Suntory in 1992, and then advocating in favour of his Scottish roots for Dewar’s in 2004.

Jim Beam had a conga line of celebrity endorsers, from singer Betty Davis to actor Leonardo DiCaprio. Japan offered many actors geographical anonymity, with Suntory and Nikka hiring actors Mickey Rourke, Matt Dillion and Keanu Reeves, and musician Ray Charles, to speak for its brands. Two Rat Packers, Sammy Davis Jr and Peter Lawford, also signed up as spokespeople for Suntory whisky in the 1970s. Matthew McConaughey fronts as creative director and a presenter to Wild Turkey, replacing actress Mila Kunis. Scotch brands have recruited celebrities since at least 1951, when Surrealist artist Salvador Dali shilled for Old Angus Scotch, with recent campaigns for Johnnie Walker fronted by actors Christina Hendricks and Jude Law, and footballer David Beckham now synonymous with Haig Club.

During the past two decades, a new trend has been celebrity investors: Bob Dylan financed Heaven’s Door whiskey and distillery in Nashville; Irish mixed martial artist Conor McGregor established Proper No. Twelve, an Irish whiskey; and Outlander star Sam Heughan launched his own Scotch. The trend even stretches beyond whisky. George Clooney launched Casamigos Tequila and Dwayne ‘The Rock’ Johnson founded Teremana Tequila last year, selling 300,000 cases in just nine months. Of course, celebrity pulling power can be lucrative: last year, Proximo paid McGregor US$600 million for his Proper No. Twelve brand.