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Singers are known to avoid dairy products, chocolate, fried food, and spicy meals before a performance. Legendary vocalist Judy Garland famously only drank room-temperature liquid before and during shows. As she shared in a 1967 interview with The Evening Sun newspaper, “Hot liquids cause swelling in the throat. Only drink tepid water or wine.” Factual or flawed medical advice aside, the point remains: Singers can be picky about their preferred foods. Frank Sinatra was certainly picky — but not in the throat-centric approach of his fellow performers.
Sinatra was all about Tootsie Rolls. According to the official Tootsie Roll website, he named the chewy, chocolatey treat as his all-time favorite candy. Sinatra was also known to request 12 rolls of cherry-flavored Life Savers candies and 12 rolls of assorted-flavored Life Savers in his dressing room at every show. The rider also included a requirement of one bag of miniature Tootsie Rolls.
Tootsie Rolls were invented in 1896 in New York City, and as of 1968 are headquartered in Chicago – the same city that Sinatra proudly called “My Kind of Town.” Although Sinatra himself was born in New Jersey, he came to Chicago as a no-name band singer in 1939, and would get his professional start in the Windy City — not unlike Tootsie Rolls, a fellow East Coast transplant.
Ol’ Blue Eyes was a notorious Tootsie Roll fan
In 1915, the year Frank Sinatra was born, an entire package of Tootsie Rolls cost just $0.05. Fast forward, in 1942, Sinatra himself appeared in a Tootsie Roll advertisement alongside fellow vocalist Peggy Lipp. From 1942 through 1945, Tootsie Rolls were even included in G.I. rations for the American military during World War II.
Another 1942 Tootsie Roll ad depicted a smiling, uniformed soldier joking, “Sure I take candy from a baby … when it’s Tootsie Rolls!” The ad continued, “Tootsie taste gets ’em all … from marble-shooters to leathernecks.” Other Tootsie Roll advertisements from the same year show mock-frustrated youths asking, “Can’t a guy call a Tootsie Roll his own?”, expanding on the ad campaign theme that Tootsie Rolls are so tasty that adults steal them from kids. Whether or not Sinatra ever swiped a Roll remains to be seen — but the singer did choose to be buried with his favorite candy when he died in 1998.
According to biographer Alan W. Petrucelli’s 2009 book “Morbid Curiosity: The Disturbing Demises of the Famous and Infamous,” Sinatra’s coffin was packed with Tootsie Roll candies, a roll of cherry Life Savers, a pack of cigarettes, and a bottle of bourbon (the singer was an outspoken Jack Daniels fan). Even though Ol’ Blue Eyes was a larger-than-life star, he still appreciated the simple pleasures to the end.
