50 free Teddy Bear trivia questions with answers — trivia quiz, new questions added Aug 2026.
40 free Teddy bear trivia questions with answers. Teddy bear trivia for anyone who still has one on the shelf. The quiz starts with the 1902 Mississippi hunt and the Washington Post cartoon that gave the toy its name, follows Morris Michtom's candy-shop bear and Richard Steiff's 55 PB, and then wanders through a century of famous bears: Winnie-the-Pooh and the real Winnipeg, Paddington's marmalade, Rupert, Corduroy, Sooty and Bungle, the Care Bears, Teddy Ruxpin, Fozzie, Smokey, Build-A-Bear and Seth MacFarlane's Ted. Most questions are answerable by anyone who grew up with these characters; a few - Steiff's model number, Aloysius's poet, the BBC's use of 'The Teddy Bears' Picnic' - are for the collectors. It suits a family quiz, a baby shower round, or National Teddy Bear Day on 9 September. Every answer has been checked against a reference page and carries its source.
30 of 50 questions with answers and explanations. Play the quiz
Q 01The teddy bear is named after which US president?
Theodore Roosevelt
He loathed the nickname 'Teddy'; the toy took it anyway after a 1902 hunting trip in Mississippi.
Q 02Why did the president refuse to shoot the bear on the 1902 Mississippi hunt that gave the toy its name?
It had been tied to a tree
His attendants had cornered, clubbed and tied a black bear to a willow tree; a Washington Post cartoon of the scene ran a few days later.
Q 03Which cartoonist's 1902 Washington Post drawing of Roosevelt sparing a bear sparked the teddy bear craze?
Clifford K. Berryman
The bear in the cartoon shrank into a cute cub in later versions, which is more or less what happened to the toy.
Q 04What did Morris Michtom sell at the Brooklyn business where he displayed the first 'Teddy's bear'?
Candy
The Brooklyn shop was at 404 Tompkins Avenue; Michtom went on to found the Ideal Novelty and Toy Company.
Q 05Which toy company did Morris Michtom found on the back of his teddy bear?
Ideal
Ideal went on to make Rubik's Cube, Betsy Wetsy and Mr. Machine before being swallowed by CBS Toys in the 1980s.
Q 06Richard Steiff's jointed teddy bear was first shown at a toy fair in March 1903 in which German city?
Leipzig
An American buyer promptly ordered 3,000, and the bear craze was on both sides of the Atlantic.
Q 07What was Steiff's very first product when Margarete Steiff started the company in 1880?
An elephant pincushion
The seamstress from Giengen sold felt elephants as pincushions; children started playing with them instead.
Q 08What trademark did Steiff introduce in 1904 to foil counterfeiters?
A button in the ear
The 'Knopf im Ohr' was devised by Margarete's nephew Franz; genuine antique Steiffs are still identified by it.
Q 09What is the model designation of Richard Steiff's 1903 bear, the first with movable arms and legs?
55 PB
55 stood for its height in centimetres, P for plush and B for beweglich, 'jointed'.
Q 10Early teddy bears were covered in which fabric, giving them their tawny colour?
Mohair
They also had long realistic snouts and humps; the cute, flat-faced bear evolved over the following decades.
Q 11Which country made the 19-metre teddy bear that set a Guinness size record in 2019?
Mexico
It was built in Xonacatlan in the State of Mexico and measured 63 feet 8 inches long.
Q 12'The Teddy Bears' Picnic' began as a 1907 instrumental by John Walter Bratton. Who added the words in 1932?
Jimmy Kennedy
The Irish lyricist also wrote 'Red Sails in the Sunset'; Henry Hall's BBC Orchestra recorded the first vocal version the same year.
Q 13For more than 30 years BBC engineers used 'The Teddy Bears' Picnic' for what purpose?
Testing audio equipment
Its wide dynamic and frequency range made Henry Hall's 1932 recording a handy calibration tool into the 1960s.
Q 21Which former Beatle produced the BAFTA-winning animated short Rupert and the Frog Song?
Paul McCartney
Its song 'We All Stand Together' reached number three in the UK in 1984.
Q 22What is Corduroy, the department-store teddy bear of Don Freeman's 1968 picture book, missing?
A button on his overalls
A girl named Lisa buys him with her own money and sews the button on; A Pocket for Corduroy followed in 1978.
Q 23Teddy Ruxpin, the best-selling toy of 1985 and 1986, told stories using what technology?
A cassette deck in his back
Q 14Christopher Robin Milne's teddy bear, the model for Winnie-the-Pooh, was bought at which London store?
Harrods
Milne bought it in 1921; the original toys have been on display at the New York Public Library since 1987.
Q 15Winnie-the-Pooh's 'Winnie' comes from a real black bear at London Zoo. What was she named after?
The city of Winnipeg
Lieutenant Harry Colebourn bought the cub for $20 at a train stop in White River, Ontario, in 1914 and left her at the zoo on his way to the Western Front.
Q 16Where did the 'Pooh' half of Winnie-the-Pooh's name come from?
A swan
The Milnes met the swan on holiday; the bear's stories are set in the Hundred Acre Wood, modelled on Ashdown Forest in Sussex.
Q 17Where in London do the Brown family find the bear from darkest Peru?
Paddington station
He is sitting on his suitcase with a note reading 'Please look after this bear. Thank you.', sent from darkest Peru by his Aunt Lucy.
Q 18Author Michael Bond was inspired to create Paddington after buying a lonely teddy bear on which occasion?
Christmas Eve 1956
He bought the last bear on the shelf as a present for his wife; A Bear Called Paddington followed in October 1958.
Q 19Which actor voices Paddington in the 2014 film and its sequels?
Ben Whishaw
Colin Firth was originally cast but stepped aside; Bonneville plays Mr Brown and Grant the villain of the second film.
Q 20Rupert Bear first appeared in 1920 in which British newspaper?
The Daily Express
Mary Tourtel drew him; he lives in Nutwood in a red jumper and yellow checked trousers, and annuals have appeared every year since 1936.
His mouth and eyes moved in sync with the tape; Worlds of Wonder, the maker, went bankrupt within three years.
Q 24The Care Bears began life in 1981 as artwork for what?
Greeting cards
American Greetings commissioned Elena Kucharik's paintings; Kenner's plush toys followed in 1983 and each bear got a 'belly badge'.
Q 25What is the ultimate weapon of the bears who live in the Kingdom of Caring's cloud city?
The Care Bear Stare
They line up and beam light from their tummy symbols; the 1985 film was the top-grossing non-Disney animation of its day.
Q 26Build-A-Bear Workshop was founded in 1997 by Maxine Clark in which city?
St. Louis
Customers stuff their own bear and tuck a fabric heart inside; a 2018 'Pay Your Age' promotion caused queues so long stores had to shut.
Q 27What is Fozzie Bear's catchphrase after telling a joke on The Muppet Show?
Wocka wocka!
Frank Oz performed him from 1976 to 2000; the name honours Muppet builder Faz Fazakas, and Statler and Waldorf never laugh.
Q 28In the 2012 film Ted, the foul-mouthed teddy bear comes to life because of what?
A boy's childhood wish
Seth MacFarlane directed and voiced Ted opposite Mark Wahlberg's John Bennett; it set a record for an original R-rated comedy opening.
Q 29Sooty, Britain's longest-running children's TV bear, was originally a glove puppet bought where in 1948?
Blackpool
Harry Corbett found him on holiday; the catchphrase 'Izzy wizzy, let's get busy!' and friends Sweep and Soo came later.
Q 30Aloysius, Sebastian Flyte's teddy bear in Brideshead Revisited, was modelled on the real bear of which poet?
John Betjeman
Betjeman's bear was called Archibald Ormsby-Gore; the 1981 TV series used a bear named Delicatessen owned by actor Peter Bull.