Secrets of the penny candy jar: From Tootsie Rolls to Necco wafers, the real story behind every nostalgic treat

Whether you loved Milk Duds, Pixy Stix, the Circus Peanut or the Charleston Chew, these histories are sweet

By: Susan Benjamin

Excerpted from “Sweet as Sin”

One of the beauties of the penny candy store was how you collected your stash. Some candies were unwrapped, and you picked these up with a small scoop, a set of tongs, or, at the beachside shops when no one was looking, your bare hands. Others were individually wrapped. These candies were what got penny candy out of the apothecary and grocers and into mainstream shops. Wrapped and ready, these candies were labeled, sanitary, and above all, self-contained. What better way to end our penny candy search than with a few favorite wrapped selections.


The history of the Tootsie Roll began with an Austrian immigrant named Leo Hirshfield. The rumor—actually a published and respected rumor—was that Hirshfield started making his candy in a little shop in Brooklyn, New York. He named his penny candy the “Tootsie Roll” because it was a roll of toffee-like chocolate and his daughter Claire was nicknamed “Tootsie.” Later, a larger company, Stern & Staalberg, bought Hirshfield out. Somewhere along the way, Hirshfield hand-wrapped his candy so it was clean, hygienic, and could travel from one store to another without needing to be poured and weighed. Hirshfield, the immigrant candymaker, was the American dream and success story all rolled into one.

That’s the story I love, and I’ll stick to it.

But the truth is more like this: Leo Hirshfield really was an Austrian immigrant, but he was an inventor at the confectionery company Stern & Staalberg with numerous patents to his name. He worked his way up the company ladder, eventually becoming a vice president. He did invent the Tootsie Roll and likely named it for his daughter, although “Tootsie” had been a term of endearment since the early 1900s as well as a loving name for a young one’s foot. As for Hirshfield, after some wrangling with Stern & Staalberg, he either lost or left his job. He attempted to start another, but that, too, failed. The wealthy but defeated inventor went on to shoot himself in a New York hotel.

See why I like the first story better?

Other Tootsie Roll insights: The Tootsie Roll was a heat-safe chocolate that held up well all year round. Among the many candies appearing in the rations of World War II soldiers, it was so durable and dependable, soldiers used “Tootsie Roll” as another name for bullets. Stern & Staalberg later became known as the Sweets Company of America, then Tootsie Roll Industries, which it remains today.


Caramels are an American invention that emerged from the European caramelized sugar of the seventeenth century. They are the essence of the praline, which the French brought to Louisiana in the 1760s. The caramel came into its own in the late 1800s, around the time when Hershey started the Lancaster Caramel Company. The Encyclopedia of Food and Beverages, published in 1901, gives this definition of caramel: “Sugar and corn syrup cooked to a proper consistence in open stirring kettles, run out in thin sheets on marble slab tables and cut into squares when cooled.” That recipe is not an industry standard: Hershey, compliments of his Denver caramel-making employer, knew to substitute milk for paraffin wax. Either way, caramel played a welcome part in candy where, with nuts, a chocolate coating, or simply solo, it is one of America’s favorite candies today.


Milk Duds were invented by the F. Hoffman Company of Chicago in the 1920s and later made by Holloway. This was at a time when marketing was becoming ever more sophisticated, and marketers knew that a product’s name meant everything. No more putting the candymaker’s name on the label—it worked for Hershey, the Smith Brothers, and Oliver Chase, but times were changing. The name needed zing!

But how do you give zing to a candy you intended to be a perfectly round chocolate-covered caramel ball that sagged and dented? It wasn’t a ball. It was a dud. And that’s when someone in the company came up with a great idea. Let’s call it “Milk Chocolate Duds!” Too long? OK, then just “Milk Duds!” It’s too bad that person’s identity has been lost in the annals of history. It was the first and only time, as far as I know, that a candy was named for its liability.

Another caramel favorite with a spicy name was the Sugar Daddy, invented by Robert Welch, a chocolate salesman for the James Welch Co. The Sugar Daddy was named for the other sugar daddy, an older gentleman who obliges a younger woman—his wife, his mistress, or whoever she may be—with all the comforts his fortune can supply. Apparently, that sugar daddy originated with one Alma Spreckels. It’s the pet name she gave her considerably older husband, heir to the Spreckels’s sugar fortune in 1908. Originally, the candy was called the “Papa Sucker.” We’re all glad they changed it. Can you imagine calling it “Papa Sucker” today? It’s almost too embarrassing to talk about.


The Mary Jane was one of the earliest toffees, and its beginnings in Paul Revere’s former home is beyond the greatness any toffee can reasonably expect. Still, a rush of other toffees followed, such as the Bit-O-Honey, first made in Chicago in 1924, using honey instead of the standard corn syrup and sugar. It’s not clear if the name was influenced by Clarence Crane’s increasingly popular Life Saver family with the pronounced “O.”

Another old timer is the sassy Squirrel Nut Zipper, which has one of the most perplexing names in candy history. The Squirrel Nut Company, then called the Austin T. Merrill Company, started in 1890 in Boston, Massachusetts. The business soon moved to Cambridge, Massachusetts, where the new owner Mr. Perley G. Gerrish sold his freshly roasted nuts throughout the Boston area by horse and carriage.

The company produced candy as well as nuts and came out with the Squirrel Nut Zipper in 1926. The name “Squirrel Nut,” is for the company, obviously. The “Zipper” was an illegal Prohibition-era cocktail. Remember how the temperance crowd claimed candy would lead to alcoholism in kids? Well, the candy companies had their say, putting a humorous twist on the old adage, “If you can’t beat them, join them.”

Eventually the Squirrel Nut Company’s nuts went to south to Antarctica with Admiral Richard Byrd, alongside its stateside neighbor’s NECCO Wafer. Also like the wafer, the nuts were also sent out during World War II. A soldier stationed in the Philippines wrote home: “I received a Christmas box with a pack of your peanuts in it. They were the only nuts that arrived without worms.”

Today, the company, now called Squirrel Brand and Southern Style Nuts, is based in McKinney, Texas. The Zipper is still in Massachusetts, where it’s now made by none other than NECCO.


In the penny candy store, the toffee found itself in places in-between its naked self and fully dressed in candy bar chocolate. One example is the Heath Toffee Bar, a candy quite different in nature from the other misbehaving Prohibition-era candies we’ve discussed. The Heath Toffee Bar was started by a school teacher, L. S. Heath, in Illinois. Heath was actually looking for a line of work for his two oldest sons when he found a small confectionery for sale.

In 1914, the shop opened selling ice cream, fountain drinks, and sweets. One thing lead to another, and soon candy salesmen were hanging around Heath’s store, talking, as they do, about candy. One of them was raving about another candymaker’s toffee recipe. The Heath brothers were intrigued. I bet you know what happened next. They called it Heath Toffee.

In 1931, L. S. Heath quit his job teaching school after twenty years and joined the candy business, as did his two sons. It was the younger generation who thought up a great marketing idea: Why not sell our candies through dairymen who went from house to house with their milk, ice, and cheese? Just add Heath Toffee to the list, and customers will add it to their purchases along with other products. And, of course, they did.

But the Heath Toffee Bar was different from other bars, which initially caused confusion. First, the bar was one ounce, while others were four; this convinced consumers they were buying a penny candy and not a five-cent bar. Second, the design had a large “H” at either end, with the “eat” in small caps in the middle: HeatH. Shoppers thought the name of the company was H&H with the “eat” telling them what to do with it. A third problem was that the packaging, name aside, made it look like the laxative Ex-Lax. Salesmen weren’t sure what they were supposed to sell.

The Heath Toffee Bar took off anyway and is made by Hershey today.


Don’t be deceived by the title. We really are talking about the Charleston Chew, which is not exactly a taffy and not exactly a toffee, and to be perfectly honest, I’m not exactly sure what it is. But I can tell you this: the Charleston Chew, that dense marshmallow-taffy-toffee substance covered with chocolate is more like the Squirrel Nut Zipper, in spirit anyway, than the Heath Toffee Bar.

It was first made in 1925 and spent most of it life in Boston, which is one Zipper connection, although most people think its name refers to Charleston, South Carolina. I imagine it has a pretty good following there. The other connection is that the Charleston Chew is tied to Prohibition, named for the dance, the Charleston, which showed up in movies with flappers dancing merrily in-between sips of the Zipper (quite possibly) and other speakeasy drinks.

While we’re discussing theater and dancing, the Fox Cross company that invented the Charleston Chew began when Donley Cross, a Shakespearean actor in San Francisco, fell from the stage, injuring his back and ending his career. The logical next step for Cross was to start a candy company with his friend, Charlie Fox. I know, it doesn’t make much sense, but that’s candy.


The Turkish Taffy was another flop that rose in stature to become a pop-culture favorite and, after a brief hiatus, remains so today. I remember eating it as a kid and feeling the sticky sweetness warm my mouth.

Bonomo Turkish Taffy was not made by a Turkish candymaker but by Austrian immigrant Herman Herer in 1912. At the time, he was trying to create a marshmallow candy for M. Schwarz & Sons of Newark and added too many egg whites. The candy was a dud. But it got Herer thinking. He experimented with the recipe, then sold his business to M. Schwarz & Sons who hired Herer back. Herer kept experimenting and finally succeeded in making the only flat taffy in the world. Its name was Turkish Taffy.

In nearby Coney Island, the Bonomo family was looking for something new to do. Albert, who really was Turkish and had immigrated to the United States in 1892, started his career selling candy from a pushcart in Coney Island. He then owned an ice cream company, where he sold ice cream from a horse-drawn covered wagon. Eventually he opened a candy and ice cream factory on the first floor of his house, living on the second floor and housing about thirty workers on the third floor.

In 1919, Bonomo’s two sons, Vic, who had just returned from World War I, and Joe, a bodybuilder and football player, joined the business. In 1936, Bonomo bought M. Schwarz & Sons and with it the Turkish Taffy, making the taffy truly Turkish. Eventually the brothers took over and ran the company until Joe left to pursue a career in Hollywood as an actor, stuntman, strongman, and health writer. Vic then ran the company on his own.

The Turkish Taffy remained a mainstay of American confections, thanks in part, to its signature tag line “Crack it up,” and instructions on the packaging: “Crack It Up!—Hold Bar in Palm of Hand—Strike against Flat Surface—Let It Melt in Your Mouth.” Tootsie Roll eventually bought the candy and ran it into the ground. But only temporarily. The Turkish Taffy is back, now owned by a company called Bonomo. There is no relation between the company and the Bonomo family, but the taffy still tastes good.


Another centerpiece of the candy store was the wild flavors, colors, and textures that promised kids a culinary (of sorts) experience. The endurance of these sprightly selections has much to do with their flexibility, sometimes shifting purpose as well as packaging and taste. One example is Pixy Stix, the paper straws filled with sugar so powdery and light it practically vanishes when eaten.

Originally a drink flavoring, much like Kool-Aid, the sugar powder was made in the 1930s and called “Frutola.” But when inventor J. Fish Smith found that kids preferred eating it, he turned it into an eating candy, which he sold with a spoon. In the 1950s, Sunline Inc. made it the fun-lover’s candy it is today. Outside of its straw-like wrapper, it would just be another tasty but highly processed sugar. But who cares?

Another candy that is perplexing in flavor, texture, and history are the much loved (and loathed) Circus Peanut. This curious candy originated in the 1800s. It was quite possibly for sale at travelling circuses but was also found in candy stores, general stores, and other places where penny candy was sold. The texture is soft as a sponge, spongy as a marshmallow, and flavored like a banana. The circus peanut was never what you’d call prestigious and various versions entered the candy arena for decades. One in particular is a surprise.


In 1963, General Mills used the circus peanut as a prototype for the charms in Lucky Charms. Today, knockoff Charms are cropping up at candy stores everywhere, minus the flakes. As you may remember, I sampled a few on my way back from Wilbur’s. Very satisfying in a lighthearted way.


Is Chick-O-Stick another Life Saver rip off with the “O” at its center? If so, that’s about all the two sweets have in common aside from their presence in candy stores. The orange- and coconut-speckled Chick-O-Stick began its life in Canada, known as Chicken Bones. It was invented by Frank Sparhawk, an employee of brothers James and Gilbert W. Ganong, who opened their shop in 1873. The candy was a cinnamon-flavored candy shell filled with bittersweet chocolate, that looked like chicken bones. The Ganong’s company is still operating today and is still family owned.

So successful were Chicken Bones that they spread south, all the way to Texas, where another family-owned business, Atkinson Candy Company, apparently found them. The Atkinson Candy Company began in 1932 after Basil Atkinson was laid off from his job at a foundry. He borrowed a truck, dug up some cash, and loaded his wife and sons into the cab for the two-day drive to Houston. There he loaded up on candy and tobacco. He began selling these items to small shops, eventually setting up a wholesale distribution center.

Eventually, Basil realized he could make candy just as well, make that better, than the other guys. With help from his wife, he got to work. In the late 1930s, he came up with a candy that looked like Southern-fried chicken bones (and the Chicken Bones candy that already existed). Basil decided he should name them “Chicken Bones,” but Ganong decided he shouldn’t. Atkinson renamed his candy Chick-O-Stick, with the Life Saver-esque “O” in the middle. It was a southern favorite for years and is nationally known today.


Wilma Green is an artist whose life could be her own portrait. She is an activist, a community organizer, a mother, a teacher, and a friend. This is her candy story.

When I was a kid, my mother would send my twin brother, William, and me to Star Foods Grocery with empty RC Cola bottles and some money. We’d exchange the bottles for more RC for her and two Chick-O-Stick; one for her and one for my brother and me to share. They had to be Chick-O-Stick. She loved Chick-O-Stick. I don’t know if it was her background coming from the South, but she did.

That was in the ’60s in Chicago. We lived in the largest public housing development in the world—the Robert Taylor housing project. People had migrated from the South during the Depression and built these communities over the years. It was a black metropolis. We did everything there—went to school, saw the doctor. Everyone who went to the Star Foods Grocery knew the owners and everyone got credit. Some people say it was segregation, but I don’t know. I always felt good. . . . I always knew everyone was watching out for me there.

My mom was raising ten kids on her own since my father had died. My brother and I were the youngest. The three oldest were in Arkansas picking cotton with my grandparents. All of us went there in the summer to help out, but my brother and I were too young to pick. It was because of that work my grandparents were able to buy their own house.

During WWII, when my mom was a teenager, she had the opportunity to work at a plant that made parts for bombs like Rosie the Riveter. She paid someone else to pick the cotton; the owners didn’t mind because they didn’t know the people who worked there—just the number of hands. They weren’t really people to them. Eventually she worked at an electronics company that was right next to a candy company. She would go there and get the second-rate candy, you know like broken pieces of chocolate, which she’d also give to us. My brother and I would sell it to other kids and get the good stuff for ourselves, like Now and Laters.

But, as I said, once a week, my brother and I would take the RC bottles and get more RC for my mother and Chick-O-Stick for all of us. I think the candy originated in the south—it was probably a piece of her memory. It’s amazing how candies bring up memories.

It’s nice to revisit those memories. I really love that.


No one knows when people started enjoying lollipops, although Charles Dickens wrote about hard candy on a stick in the 1800s. In the United States, around the time of the Civil War, people started sticking pencils into hard candies to eat them. At home, people basically dropped a mound of hard candy onto parchment or wax paper, stuck in a stick, let it dry, and then enjoyed the treat. But commercially not a lot was going on.

Then, in 1895, Chicken Bones owners Gilbert and James Ganong began inserting sharp wooden sticks into their hard candy, creating one of the first commercial lollipops in the northern hemisphere. They called it an “all day sucker.” That changed in 1908 when the Bradley Smith Company starting manufacturing the “Lolly Pop,” which was named after George Smith’s favorite racehorse. Their inspiration was a chocolate-caramel taffy on a stick, made by Reynolds Taffy of West Haven, Connecticut, that resembled the Sugar Daddy.

George Smith attempted to get ownership of the name “Lolly Pop,” but the US Patent Office turned him down, as the term was listed in an English dictionary of the early 1800s, spelled “lollipop.” There it was described as “a hard sweetmeat sometimes on a stick.” Eventually, Smith got the rights to “Lolly Pop” with that specific spelling, but it was negligible. People began using both names interchangeably and have ever since.

By the 1920s, numerous lollipops seemed to appear in penny candy stores and other places. There was the Dum Dum, made in 1924 by the by the Akron Candy Company, which evidently knew the marketing potential of a name; the company’s salesman named the lollipop “Dum Dum,” thinking kids could easily remember it and ask their parents to buy some. Obviously, he was right. The Tootsie Pop, essentially a panned Tootsie Roll, came around 1931, and, in the 1940s, after parents expressed concern that kids would choke on the stick, the Saf-T-Pop, with a round holder, was released.

Excerpted from “Sweet as Sin” by Susan Benjamin. Published by Prometheus Books. Copyright 2016 by Susan Benjamin. Reprinted with permission from the publisher. All rights reserved.