The Famous Actor Who Sparked Frank Sinatra's Love Of Jack Daniel's

Crooner and Hollywood actor Frank Sinatra was known for cavorting in Sin City with his merry band of cohorts, aka the Rat Pack, and booze was a big part of their scene. Sinatra may have been a fan of Chivas Regal scotch, but it was Jack Daniel's whiskey that was his all-time tipple of choice. And, according to a transcript of Sinatra (via Globe Newswire), it was a Hollywood legend who likely introduced Jack to Frank: Humphrey Bogart. According to Nelson Eddy, a historian of Jack Daniel's, Sinatra called Jack Daniel's "the nectar of the gods" and became the famed Tennessee whiskey's best unpaid spokesman (although the distillery kept him stocked with free bottles) (via Forbes). Around 1955, the singer began bringing JD on stage with him to sing its praises, which did wonders for the brand's sales. He was even supposedly buried with a bottle when he died in 1998. 

During a 1982 concert at Caesar's Palace in Las Vegas, Sinatra recalled a night at Bogart's home — where friends would gather and the original Rat Pack formed — where Bogie offered him a drink of Jack Daniel's after dinner, which he'd never had, and he fell in love with the whiskey. Sinatra's go-to way of drinking Jack was his 3-2-1 method — that is, three pieces of ice, two fingers of whiskey, and one finger of water. Sinatra idolized Bogart, so it made sense he'd emulate his drink of choice. Still, like much history, there are other possibilities for who might have been responsible for Sinatra's introduction to his favorite whiskey. 

In the boozy history of exactly who turned Frank Sinatra on to Jack Daniel's, there are a few other contenders. Humphrey Bogart's wife, actress Lauren Bacall, was a huge Jack Daniel's fan, and reportedly introduced it to Bogie. But it's also possible that Bacall may have influenced Sinatra's choice of booze since he had a crush on her (and dated her after Bogart's death) and may have been swayed by her personal tastes. All three were members of the brand's exclusive Tennessee Squires Association that began in the 1950s and they would sometimes wear blazers featuring Jack Daniel's insignia on the breast.

There was another actor friend of Sinatra's who Jack Daniel's historian believed introduced him to Jack Daniel's. Jackie Gleason of "The Honeymooners" was allegedly responsible for giving him his first taste of the Tennessee whiskey way back in 1947 in a New York City bar. In a 1986 interview in Playboy, Gleason made this claim stating he believed the first time Sinatra got drunk was with him. "I said, 'Jack Daniel's! That's the way to start. And to this day, he drinks Jack Daniel's," Gleason recalled (via the Birmingham Post-Herald). Sinatra's love for Jack Daniel's became a thing of legend, even taking it to the grave (just one of the more unusual Jack Daniel's facts you should know). But whether it was Bogie, Bacall, or Gleason who introduced him to it, it paid off handsomely for the distillery.