The love affair began one night in the 1940s when Frank Sinatra asked his pal Jackie Gleason to recommend a drink that would get him "smashed." Gleason shot back: "Jack Daniel's! That's a good place to start." The crooner soon became J.D.'s most conspicuous imbiber. He kept a bottle nearby onstage. He consumed it late at bars after his sidekicks told the squares to go home. When he died in 1998, he was buried with a flask of the stuff. Jack Daniel's wasn't popular when the singer first took a fancy to it; with Sinatra's endorsement, it became America's best-selling whiskey. "It was one of those authentic relationships," says Matt Blevins, senior brand manager at the Jack Daniel Distillery in Lynchburg, Tenn. "We never paid him."
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