Tootsie Roll
0Loading crowd target
0Loading crowd target
6correct to beat the crowd
40 free Tootsie Roll trivia questions with answers — trivia quiz, new questions added Oct 2026.
The Tootsie Roll has been in American pockets for well over a century, and it has barely changed. The small brown chew has outlasted price rises, ingredient shortages and whole generations of rival sweets, and it turns up in more odd corners of history than most people would guess. This quiz covers the full story: the immigrant candy maker who invented it and how it got its name, the recipe and what goes into it, the lollipop spin-off and its famous television commercial, the people who have run the company, and the sister brands that share its factories, from mints and gumdrops to caramel pops. It suits candy lovers, Halloween party hosts, teachers building a food-history round and anyone who has ever wondered about the question that commercial keeps asking. Every answer comes with a short explanation, so the questions work on screen or read aloud.
30 of 40 questions with answers and explanations. Play the quiz
Q 01In a much-told Korean War story, Marines at which frozen battle radioed for Tootsie Rolls, their code for mortar shells?
Chosin Reservoir
Chosin Reservoir veterans tell of the real candy turning up instead; the frozen rolls gave them energy and patched bullet holes in vehicles.
Q 02In the classic animated Tootsie Pop commercial, which animal takes the lollipop and crunches it after only three licks?
Owl
Owl is the one a boy turns to after a cow, a fox and a turtle each admit they always end up biting, and the bird does exactly the same.
Q 03Leo Hirschfield named the Tootsie Roll after the childhood nickname of which member of his own family?
His daughter
His daughter Clara, about five when the candy got its name, went by Tootsie at home.
Q 04Which crooner, who posed for a 1940s Tootsie Roll advertisement, is said to have been buried with the candy?
Frank Sinatra
Frank Sinatra is said to have counted the chewy rolls as his favorite sweet, and a 1942 advert pictured him alongside Peggy Lipp.
Q 05According to the company, what does the Tootsie Roll recipe call for adding to each day's fresh mix?
Some of yesterday's batch
Some of yesterday's batch goes into each new one, a graining step that links every Tootsie Roll to the ones made before it.
Q 06Dubble Bubble, now a Tootsie Roll brand, made which color standard for gum because the factory had no other dye?
Pink
Pink was the only food coloring on hand when Fleer employee Walter Diemer mixed his first workable bubble gum in 1928.
Q 07Which sitcom built a 1993 episode around a Junior Mint, a Tootsie Roll Industries candy, falling into a surgery patient?
Seinfeld
Seinfeld sent the mint flying from Kramer's hand into the open incision, and the episode earned Michael Richards his first Emmy for the role.
Q 08A long-running rumor says a Tootsie Pop wrapper showing which picture can be traded in for a free lollipop?
An archer and a star
An archer and a star never earned a prize from the company, though some shops played along. Since 1982 it has mailed children a short story about the wrapper instead.
Q 09During which conflict did Tootsie Rolls become a standard part of American field rations because they kept so well?
World War II
World War II rations carried the candy from 1942 to 1945 as quick energy, since it stayed fresh for months in almost any climate.
Q 10Leo Hirschfield wanted the Tootsie Roll to taste of chocolate while avoiding which headache for candy sellers?
Melting in heat
Melting in heat kept real chocolate off summer counters before refrigeration, so a chocolate-tasting chew that held its shape had the season to itself.
Q 11Since the late 1960s, which Midwestern city has housed the headquarters and main factory of Tootsie Roll Industries?
Chicago
Chicago took over from the East Coast in 1968, and the plant on its South Side still turns out tens of millions of the chewy rolls every day.
Q 12The Tootsie Roll is credited as the first penny candy in the United States to be sold in which way?
Individually wrapped
Individually wrapped for a cent apiece, it stayed cheap enough to become a Depression-era favorite.
Q 13A Tootsie Roll is usually described as sitting between a caramel and which other chewy confection?
Taffy
Taffy is the nearest cousin, but the 1908 patent has the candy baked at a low temperature for about two hours, leaving it denser than airy pulled sweets.
Q 21In which city did Leo Hirschfield create the Tootsie Roll before the business moved to New Jersey and then the Midwest?
New York
New York was where the candy was first made and sold for a cent apiece, decades before the company crossed the Hudson and later settled in the Midwest.
Q 22Leo Hirschfield, the candy maker behind the Tootsie Roll, emigrated to the United States from which European country?
Austria
Austria was the homeland of his father too, a candy maker by trade, and the son followed him into the business.
Q 23Bromangelon, a dessert powder created by the Tootsie Roll's inventor, went on sale a few years before which rival brand?
Jell-O
Jell-O eventually drove Bromangelon off the market, though Leo Hirschfield's mix had been the first gelatin dessert powder to sell widely.
Q 14Which restaurant chain hands diners its own flavor of Andes mints, a Tootsie Roll Industries brand, after meals?
Olive Garden
Olive Garden gets a blend made only for its tables; the brand began as a shop called Andy's Candies, respelled because men disliked gifting another man's name.
Q 15The Charleston Chew, a 1922 bar now made by Tootsie Roll Industries, took its name from which of these?
A dance craze
A dance craze, the Charleston, lent its name to the bar, which was dreamed up by stage actor Donley Cross and his friend Charlie Fox.
Q 16Which lollipop brand joined the Tootsie Roll family in 1988, creating the largest lollipop maker anywhere?
Blow Pop
Blow Pop, the lollipop with gum inside, arrived with the purchase of Charms, which had bought the idea in 1973 from a firm selling it as the Triple Treat.
Q 17Crows, the black gumdrops in the Dots family owned by Tootsie Roll Industries, come in which flavor?
Licorice
Licorice Crows date from the 1890s, and the old tale that a printer misheard the name Black Rose has been debunked.
Q 18Which common allergen does Tootsie Roll Industries say is kept out of every one of its manufacturing plants?
Peanuts
Peanuts and tree nuts are barred from every plant, so the whole range is nut-free, although the chewy rolls themselves contain milk and soy.
Q 19Which 2004 comedy makes Razzles, a Tootsie Roll Industries candy, the heroine's favorite treat?
13 Going on 30
13 Going on 30 gave the sweets that start as candy and end as gum a leading part in the same year their maker was bought by Tootsie Roll Industries.
Q 20Paul Winchell, who voiced the animal that bites the Tootsie Pop on TV, originated the voice of which Disney character?
Tigger
Tigger was the ventriloquist's best-known role, and years earlier his Saturday morning children's show had been sponsored by Tootsie Roll.
Q 24In the mid-1930s the struggling Tootsie Roll maker was taken over by the family firm that supplied it with what?
Paper boxes
Paper boxes were the Rubin family's trade, and Bernard Rubin, afraid of losing a big customer, called on shareholders in person to buy their stock.
Q 25Which relation of Melvin Gordon succeeded him as head of Tootsie Roll Industries after his 53 years in charge?
His wife
His wife Ellen Gordon, already the company's president, took over in 2015; her own father had run the firm before the couple did.
Q 26Engineering students at which Indiana university built a tongue-like licking machine to test Tootsie Pops?
Purdue
Purdue students reported that their machine needed well over 300 licks to reach the center, about a hundred more than the human volunteers averaged.
Q 27Which Florida rap duo scored a platinum top-ten hit in the mid-1990s with a song titled Tootsee Roll?
69 Boyz
69 Boyz spelled the title differently from the candy, and the single spent 27 weeks climbing to its peak of number eight on the Hot 100.
Q 28Which dietary certification did Tootsie Rolls gain in 2009, more than a century after the candy first went on sale?
Kosher
Kosher certification came from the Orthodox Union, which has also approved Dots and Junior Mints from the same company.
Q 29Nik-L-Nip, sold by Tootsie Roll Industries, packs sweet syrup into tiny bottles made of which chewable material?
Wax
Wax bottles once sold for a nickel apiece, which gave the brand the first half of its name; once the syrup is gone, the bottle can be chewed.
Q 30Cella's, bought by Tootsie Roll Industries in 1985, is best known for which chocolate-covered confection?
Cherry cordials
Cherry cordials from Cella's go back to 1864, with the liquid center sealed under a milk or dark chocolate shell.