The History of An American Candy Icon: Tootsie Rolls

in Candy Blog

How many licks does it take to get to the Tootsie center of a Tootsie Pop?

Can you take a guess?

As it turns out it takes over 1000 licks to get to the gooey, chocolatey center of a Tootsie Pop.

But before there were Tootsie Pops, Tootsie Frooties, and Mr. Owl, there was Leo Hirshfield—the creator of Tootsie Rolls.

As you know, we’re all about candy history here, and since Tootsie Rolls is one of the most popular candies of all time, we thought we’d dive into the sweet history of how they came to be.

Check it out! 

The Beginning Of Tootsie Rolls

Tootsie Roll Mini

The concept for the Tootsie Roll came from Austrian-Jewish Immigrant Leo Hirshfield whose father was a candy maker. Hirshfield's history in candy is up for debate as some recognize that he started his own candy store in New York City in 1896, while others say that he was a long-standing employee of the famous confectionery company, Stern & Saalberg.

Before he created the first recipe for Tootsie Rolls, Hirshfield was credited with the creation of Bromangelon jelly powder—one of the first versions of what would become Jell-O. While working for Stern & Saalberg, Hirshfield wanted to find a way to create a chocolate-flavored candy that wouldn’t melt during the summer. (Sounds like another iconic candy that we know and love).

After much testing, he developed the Tootsie Roll—a chocolate and caramel pulled candy that had a unique texture, similar to that of a marshmallow but with more density. With support from his friends at Stern & Saalberg, Tootsie Rolls were introduced to the candy market in 1908, after earning a patent for the recipe and process.

With the initial success of Tootsie Rolls, Hirshfield merged with Stern & Saalberg which went public in 1922 and was called the Sweets Company of America.

Right out of the gate, these bite-sized treats were a hit amongst candy lovers who were intrigued by the unique flavor and small price tag of one penny. Little did they know that this invention would spawn a whole new era of sweets known as “penny candy” that would send candy-loving kids into a spiral every time they entered the store.

To this day, Tootsie Roll is credited with being one of the first penny candies on the market and is often found in the classic barrels you see in popular candy stores across the United States. 

Tootsie Roll Expands In The Big Apple

Tootsie Roll Vintage Delivery Truck


After finding initial success with the sweet treat, Hirshfield wanted to expand the production of Tootsie Rolls so he bought a four-story building in Manhattan where the brand would start to sling larger amounts of candy. During this period, Tootsie Rolls were delivered to candy stores by horse and buggy which eventually turned into custom Tootsie roll trucks labeled with the famous logo.

In 1922, after Hirshfield’s suicide in the Monterey Hotel, the brand was left without leadership, and production of the candy started to slow.

In 1935, the Tootsie Roll was acquired by its packaging company, Joseph Rubin & Sons of Brooklyn, who wanted to keep the brand alive during the Great Depression.

Around this time, Tootsie Roll hit the NYSE of which a majority of the shares were purchased by businessman Bernard D. Rubin. Upon purchase, Rubin acquired a list of shareholders and approached them in person in order to purchase the remaining shares.

Under Rubin’s leadership, Tootsie Rolls started to find its footing in the candy market again. He focused on creating a new formula for the candy and also increased the size to make the product more marketable.

With sales on the rise, Rubin was looking for new ways to capture the attention of an audience who already loved the product. This led to the invention of the Tootsie Pop—a hard-shelled lollipop with a Tootsie Roll center. This invention would rock the candy world, with consumers flocking to stores to get their hands on the sweet creation.

Tootsie Pop Assorted Flavors

Not long after the creation of Tootsie Pop came another famous invention: the flavored Tootsie Roll. These included a wide range of flavors, originally cherry, orange, vanilla, lemon, and lime, as well as a special Mega Mix bag that included specialty flavors like green apple, blue raspberry, and grape. Tootsie Frooties came after in numerous different fruit flavors, including strawberry, blue raspberry, grape, green apple, banana berry, smooth cherry, fruit punch, pink lemonade, root beer, cranberry, blueberry, watermelon, and mango.

Fast forward a few decades and Tootsie Roll made the move from Hoboken, NJ to Chicago, IL. Here it’s its massive production facility the brand started to make over 64 million Tootsie Rolls every single day. At the same time, Tootsie Roll Industries (name adopted in 1966) would go on to acquire a bunch of other candy brands including, DOTS, Crows, Cella's Chocolate Covered Cherries, Charms, Junior Mints, Sugar Daddy, Sugar Babies, Charleston Chew, and Concord Confections

Tootsie Rolls Become The WWII Staple Candy

As the candy continued to grow in popularity, it was approached by the U.S. Army to create MRE rations that soldiers could consume on the front lines. This was a practice of many confectionery companies during this time, as demand for sweets was incredibly high and ingredient costs were at a premium.

Tootsie Roll WWII Advertisement


These government contracts helped maintain the production and funding of Tootsie Rolls throughout the war and kept the doors open while many other confectionery brands shut down.

When troops came back home, their cravings for Tootsie Rolls continued and were adopted by the families reintroducing the chocolatey treat to candy lovers across the United States. 

Tootsie Roll Becomes An Enduring Icon & Pop Culture Reference

Frank Sinatra & Peggy Lipp Tootsie Roll


In the 1950s Tootsie Rolls began pushing its sweetness in advertisements of all forms. First in radio ads with America’s Cowboy Gene Autry and with famous celebrities like Frank Sinatra and Peggy Lipp. It’s even rumored that Tootsie Rolls were Frank Sinatra’s favorite candy so much so that he was buried with a few of them.

Then the brand turned to television, buying up advertising slots during children’s shows and nightly TV. At the same time, it started its first comic strip called Tootsie Roll Hero featuring the hero Captain Tootsie along with his sidekick, Rollo, and three other young cohorts named Fatso, Fisty, and Sweetie.

These stories came in full-color one-page Sunday strips, black and white daily strips, and two issues of a comic book of the same title released by Toby Press. The comic strips were a hit among kids and found its way into many local and national newspapers across the U.S.

In August of 1970 Mr. Owl made his way to the TV screen, where he would go on to become the mascot for Tootsie Rolls moving forward. By the way, did you know that you can follow him on Twitter @MrOwl. 

Tootsie Rolls Today 

Today, Tootsie Rolls is recognized as one of the largest candy manufacturers in the world churning out millions of pieces of candy every single day. The recipe, which calls for the inclusion of the previous day's batch, still remains the same. As such, there's “technically” a bit of Leo Hirshfield’s very first Tootsie Roll in every one of the sixty-four million Tootsie Rolls that are produced.

Between its classic flavor and texture, as well as its hold on candy culture over the last 100 years, Tootsie Rolls continue to be sold at candy stores across the country, handed out at festivals and Fourth of July parades, and can be found right here in our candy aisles!

Thank you for the fun and interesting story on the history of Tootsie Rolls and Tootsie Pops. They have been a favorite of mine since childhood and I have either one or both each and every week. My dad used to leave them for me in secret hiding places! It was pretty special.

Lise Dominique

The one bad thing about tootie rolls and butterfingers they are only really good around Halloween and Christmas because they get tough I guess from sitting in warehouses to long at other times but when they are fresh they are fantastic .


That was fascinating!! Ty!

David Allen

very interesting story.


Thank-You for the history lesson on Tootsie Rolls, it was very interesting and informative!

Cinnamon Middleton

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