Frank Sinatra's Go-To Candy Was An Old-School Favorite

Most people remember Tootsie Rolls as the chewy center of an age-old question: "How many licks does it take to get to the Tootsie Roll center of a Tootsie Pop?" The animated commercial — first aired in 1970 — helped launch the chewy candy into pop culture stardom, making it a childhood staple that's been around for over 100 years. But for Frank Sinatra, the appeal wasn't about curiosity or crunch timing. The candy at the center of the Tootsie Pop was one of his favorites, first made in 1896 by Leo Hirschfield, who named it after his daughter.

In 1942, long before the cartoon owl asked his iconic question, Sinatra appeared in a Tootsie Roll advertisement. It was a simple pairing: America's rising heartthrob and one of its most enduring sweets — the original chewy candy itself. Sinatra loved the candy so much that a bag of mini Tootsie Rolls was part of his regular backstage requests — sitting right alongside the 24 Diet Cokes, Luden's cough drops, and an impressive liquor lineup.

It's not the type of thing you'd expect from a performer so synonymous with polish and control. The Tootsie Rolls stuck around — like a good lyric or a well-worn suit — dependable, familiar, and, in Sinatra's case, always within reach.

When Frank Sinatra died in 1998, his family didn't fill his casket with tributes. They filled it with what he actually reached for: a pack of Camels, a Zippo lighter, cherry Life Savers, a bottle of Jack Daniel's – which would later release premium whiskey inspired by Sinatra – and a few Tootsie Rolls. It was routine — just the kind of small, personal inventory that said more than a statue ever could.

And he wasn't alone in that habit. Sammy Davis Jr., his longtime friend and fellow Rat Packer, used to toss Tootsie Rolls into the crowd while singing "The Candy Man." For such a modest candy, it traveled well — from military rations handed out in World War II to Vegas stages. Sinatra even once dropped it into a lyric, slipping the line "Could'ya, for a tootsie roll?" into a song like it was nothing.

None of this seemed accidental — not the candy and definitely not what he drank. Frank Sinatra's favorite cocktail, the Rusty Nail containing Scotch and Drambuie — told you everything you needed to know: He liked his drinks strong and his candy simple.