The Bad Habits Frank Sinatra Took To His Grave

There are those of us who struggle for years quit our bad habits like smoking and drinking, for whom every day without a cigarette can seem like an eternity in a hell worse than anything conjured up by the various fire-and-brimstone pitching religions of the world. Lake of fire — ha! Try quitting a two-pack-a-day habit cold turkey!

Then there are the seemingly superhuman among us whose bodies somehow keep on trucking through decades of addictive wear and tear. According to Time magazine, the novelist Kurt Vonnegut joked a year before his death at 84 from injuries incurred during a fall that he was going to sue the makers of Pall Mall cigarettes for having lied to him. "I've been smoking Pall Mall unfiltered cigarettes since I was 12 or 14," he said, "The lying bastards! On the package Brown & Williamson promised to kill me."

Another one of those titans of artistic and addictive achievement was legendary crooner Frank Sinatra. The guy was never seen on stage without a glass of whiskey in his hand, a cigarette between his fingers. And not just any whiskey would do, either. For Frank, it had to be Jack Daniel's. According to the company, the singer was introduced to his lifelong friend in 1947, when comedian Jackie Gleason suggested to him: "Jack Daniels. That's a good place to start." From then on, it was Frank and Jack forever, three rocks, two fingers, and a splash of water.

Frank Sinatra died of a heart attack on May 14, 1998. According to his daughter Tina, the singer had big hopes of making it into the new millennium, but his heart unfortunately couldn't keep up. "Dad was determined to be a part of [the 21st century]," she wrote in her 2015 memoir, My Father's Daughter. "'How many more months?' he asked me. 'Eighteen,' I told him, rounding down a bit. 'Oh, I can do that,' he said. 'Nothin' to it.'" Unfortunately, that conversation came just five days before his death.

When he was buried a week later, his other children stuffed his pockets full of his favorite things, according to The Associated Press. His other daughter, Nancy, slipped a bottle of Jack Daniel's into his pocket, and someone else tossed in a pack of Camel cigarettes and a Zippo lighter.

But what Tina put in his pocket actually didn't represent one of his vices. She put 10 dimes in his pocket because her father always carried some around in order to be sure he could make a phone call if needed. She told CNN's Larry King that the habit came from when her brother was kidnapped in 1963. "He never wanted to get caught not able to make a phone call. He always carried 10 dimes." So to honor their father right, they made sure he was stocked with his favorite things on his way to the afterlife.

Despite the image of a hard-drinking, chain-smoking man's man that his stage presence gave to the public, Sinatra was, above all else, a professional performer, and he was not one to let his vices get in the way of what mattered most. According to his former chauffeur George Jacobs, Sinatra was able to go clean in order to prepare himself for big projects. Jacobs wrote in his 2003 memoir Mr. S: My Life with Frank Sinatra that The Voice prepared for a recording session in 1954 "with the rigor of one of his seductions." The singer got away from all distractions at his home in Palm Springs and "would rest as hard as he normally played." No whiskey. No cigarettes. He drank hot tea with lemon to keep his pipes primed. But he still had to keep up his image. "If you saw him at the studio with a drink or a smoke, they were merely props," wrote Jacobs. "His voice was his moneymaker, and he treated it with the utmost respect."

The sacrifice paid off. The sessions of which Jacobs wrote produced Sinatra's hit album Swing Easy!, part of his resurgence in popularity in the 1950s, and giving us his classic hits like "All of Me" and "Just One of those Things." Luckily, with the goodies his kids stuffed into his pockets, Frank will never have to cut back on his bad habits in the afterlife.