The Old-School Candy Frank Sinatra Loved So Much He Was Buried With It

Given his legendary status, Frank Sinatra's personal life has long been a subject of public fascination. There are countless biographies of Ol' Blue Eyes on the market, and while some may be curious about the salacious details of his private life, we're personally more intrigued by his food quirks. Sinatra had something of a sweet tooth, with a particular fondness for the classic candy, Tootsie Rolls. In fact, Sinatra loved Tootsie Rolls so much that the official Tootsie Roll website boasts that the singer was buried with them.

Just as ancient Egyptians stocked tombs with the deceased's personal belongings, Sinatra's loved ones ensured his casket was filled with relics relevant to his day-to-day life. He was buried with a variety of unconventional items, thanks in part to his daughter, Nancy. As her father was an avid fan of Jack Daniel's, she slipped a bottle in his casket. She also tucked a few other items in his pocket, including gum, cherry Lifesavers, and, of course, his beloved Tootsie Rolls.

The Chairman of the Board's love of Tootsie Rolls was well documented in his time. Sinatra required Tootsie Rolls on tour, with the candy apparently being a vital part of his pre-show food routine. A rider in Sinatra's concert contract stipulated that his dressing room must be stocked with one bag of miniature Tootsie Rolls. These were far from the only oddly specific food items on the roster. Sinatra also requested items like three cans of Campbell's Chicken and Rice Soup, a gallon of spring water, and 24 cans or bottles of various sodas (75% of which needed to be diet). 

Sinatra was more than happy to help sell his cherished Tootsie Rolls, too. In 1942, he starred in a commercial for the candy. In 1949, he recorded a version of the song "Could 'Ja?" composed by Bill Carey and Carl Fisher and originally recorded by Nat King Cole. One reason Sinatra might have been drawn to the song? It included a nod to his favorite candy with the line, "Could 'ja, for big red apple? Could 'ja, for a Tootsie Roll?"