Frank Sinatra’s Favorite Candy Is as Classic as He Is

While M&M's, Snickers, Reese’s Peanut Butter Cups, Kit Kats, and Hershey Bars might register as the biggest names in the candy world, Ol’ Blue Eyes only has eyes for another nostalgic, sweet, and chocolatey treat.

In case you missed it, we’ve been taking cues from the crooner at happy hour with a classic Rusty Nail, and as we seek out sweet snacks as he did with his weekly standing delivery for Entenmann’s Crumb Coffee Cake.

Now we find out that the best is yet to come in terms of Sinatra's favorite goodies.

Frank Sinatra’s Favorite Candy

We unearthed this nugget thanks to an old concert rider with three pages of Frank Sinatra’s “Dressing Room Requirements." Most singers, bands, performers, and acts of all kinds curate a list of requests to share with each venue where they’ll be taking the stage so the hosts know how to prepare. Some of these speak to technical details, such as lighting and audio, and others dive into the personal preferences of the stars and their posse.

Besides comfortable seating, a separate dressing room with a shower, a medical doctor on call, a color TV, and an upright piano, Sinatra requested an impressive bar lineup, plenty of sodas (75 percent diet, please), fruit and cheese platters, a selection of sandwiches (egg salad, chicken salad, and turkey), chilled seafood appetizers, and a few brand name items that are notably and specifically called out.

Luden’s Cough Drops, Lipton Tea Bags, Evian Spring Water, and Campbell’s Chicken and Rice Soup were a must, according to Sinatra’s team.

And no concert prep was complete without “1 Bag Miniature Tootsie Rolls,” the rider reveals.

Sinatra had quite a sweet spot for the small chewy chocolate candies far outside the bounds of his dressing room. In 1942, Sinatra appeared in a Tootsie Roll advertisement. Sinatra is said to have selected Tootsie Rolls as his favorite candy, “and he was even buried with them,” Tootsie Roll Industries suggests.

The History of Tootsie Rolls

Today, Tootsie Roll Industries pumps out a staggering 64 million Tootsie Rolls per day and is the top-selling chewy chocolate candy in America. The recipe has remained the same since Tootsie Rolls were invented in 1896, “when Leo Hirshfield, an Austrian immigrant, opened a small candy shop in New York City, producing the first individually wrapped penny candy from a recipe he brought from Europe,” the company explains on its website.

The cocoa is complemented with fruit-flavored undertones, and each batch apparently builds upon the last.

“Leo’s recipe required the incorporation of the previous day’s Tootsie Rolls into each newly cooked confection, a graining process that Tootsie continues to this day. As such, there’s (theoretically) a bit of Leo’s very first Tootsie Roll in every one of the sixty-four million Tootsie Rolls that Tootsie produces each day,” the brand adds.

What’s in a name, you might be asking? The candy is named after Leo’s daughter, whose nickname as a child was “Tootsie.”

In 1931, Tootsie Pops were invented as a variation on the theme. More than 125 years since Tootsie Rolls rolled onto the scene, “Industries” has ballooned to include dozens of other household names, including Andes Mints, Charms Blow Pops, Charleston Chew, Dots, Junior Mints, and Sugar Daddy. 

And while its sales are trumped by other candy bars and they’re only the most popular Halloween candy in one of the 50 states (Oklahoma), there are apparently many more loyal fans to the brand other than Sinatra alone. If you count yourself among them, you have a lot of options: Tootsie Rolls are now available in bar form, smaller “Midgees,” and egg shapes for Easter. Flavor-wise, you can do it “My Way” like Frank and take your pick from chocolate, vanilla, harvest flavors (caramel apple, candy corn, pumpkin spice, and cinnamon), and fruit chews (cherry, lemon, lime, orange, vanilla).