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Home / Trivia Nights / What Makes a Tough Trivia Question? Plus, 100 Super Hard Questions to Challenge Yourself!

What Makes a Tough Trivia Question? Plus, 100 Super Hard Questions to Challenge Yourself!

February 5, 2021 By Anastasia Voloshina Leave a Comment

Pile of question dark marks with two illuminated in blue and orange.

Surely, in the years of asking and answering trivia questions, you’ve come across some that just have that extra jazz. I’m talking about tough questions that really challenge your knowledge and make your wheels turn. And since we’re here to discuss questions, here’s one to ponder: what is it that makes a tough trivia question?

Tough questions are not limited to one category; they fit in classical music, geology, and everywhere in between. There are some criteria, though. For instance, a good way to make a question extra hard is by making it long. An excellent question will give a skilled player the chance to answer before the quizmaster finishes asking the question. Of course, it depends on the format too; written, spoken, multiple-choice, and true or false questions are all very different. 

If you’re struggling with writing tough questions, we’ve prepared a guide for you! Follow the instructions below and take your question writing to the next level. And if you’re just here for a good time, scroll down for some of the toughest trivia questions and answers!

Closeup of a pen and a notebook.
Contents hide
1 What Makes a Tough Trivia Question?
1.1 It Can Be Answered
1.2 It Has One Correct Answer
1.3 The Answer is Not in the Form of Numbers
1.4 It’s Long
1.5 Clear Phrasing
1.6 Humor
1.7 It’s Made for an Audience
2 Always Keep an Eye Out for New Trivia
3 Quiz: 100 Tough Trivia Questions Designed to Stump You
4 Questions for the People!

What Makes a Tough Trivia Question?

It Can Be Answered

Some people like to focus on the question, while they should really focus on the answer. Ultimately, the answer makes the question! That being said, if you want to write a tough question, write with an answer in mind. If the question is too difficult and can’t be answered, it’s not a good question. 

After all, the point of trivia is to answer questions. Challenge your audience and make them dig deep, but let the question be answerable! Naturally, the answer shouldn’t be on the surface. In the end, even if your audience doesn’t answer correctly, you want them to go, “Oh, I should have known that!”

It Has One Correct Answer

As we already established, a question is nothing without an answer. Always make sure your answer is 100% correct. If you have any doubts at all, leave it out; choose a different question. Likewise, avoid urban myths and legends. If you cannot back up your “fact” with research, it is simply an opinion (more on that later). 

When you’re checking the correctness of your answer, make sure that there is only one answer, too. Unless the question specifically asks for two or more answers, there should only be one right answer. If you’re willing to accept two different answers as correct, see if you can find a way to rephrase the question to make it clearer.

The Answer is Not in the Form of Numbers

Try to avoid answers in the form of numbers at all costs. If your answer is a year, age, weight, height, price, or anything in that vein, it’s either too specific and nobody will be able to answer accurately, or it’s simply boring.

Similarly, avoid questions inspired by the Guinness Book of World Records. Most people don’t know the weight of the heaviest man on earth or the diameter of the largest pizza ever made. Though you might find these facts interesting, most people don’t.

Matrix-style string of numbers.

It’s Long

Short questions tend to be boring and easy. Sure, there is a place for short and sweet questions in trivia, but forget them if you’re writing tough questions for trivia lovers! A really tough question should be long enough to give an extraordinary player an opportunity to answer before an average player. 

In other words, the question should give hints along the way. The first piece of information revealed in the question should not give the answer away. If you’re listing things, go from hardest to easiest, so only the biggest trivia whizzes can answer correctly. 

Long questions are an excellent tool in trivia. You can make a super tough question a bit easier by providing extra pieces of information. You can also present extra fun bits of trivia in the question. Finally, hearing a long and well-structured question is more entertaining than answering simple one-liners.

Clear Phrasing

If you’re working on some tough trivia questions, one thing that can easily stunt your progress is poor phrasing. Some quizmasters like to throw in curveballs on purpose and confuse their players with cheap tricks. That is a cheap trick in and of itself; don’t fall for it. Phrase your questions as clearly as possible.

For example, let’s say you’re asking about the biggest lake in the world. Do you mean the deepest lake or the lake with the largest surface area? Perhaps you meant the longest lake in the world? Do you see how the word “biggest” is very unclear? That’s the problem with using such terms. “Big” can refer to volume, weight, depth, height, length, and many other factors depending on the context. 

Similarly, if you’re asking when a certain book was written, many people might give you the year it was published. After all, some books took years to write. In that case, do you count the year the author started writing, the year they submitted their final copy to the editor, or the year the book was published? 

Another type of question that is very confusing is “Who is the biggest rock star in the UK?” “The biggest rock star” is not quantifiable or objective. If you’re referring to a title given to someone by the Guinness Book of World Records, once again, skip it. You can use this question if you really like the answer, but you absolutely have to add more information to it. For example, “One of the UK’s biggest rock stars was married to Cynthia Powell and died from gunshot wounds. Who was it?”

Though making a question confusing on purpose might equal to writing a tough question to some, it’s really not the same thing. Your audience might be confused, or they might just think you made a mistake.

Humor

An extraordinary question will not only tickle one’s brain but also provide a fun piece of trivia. Remember that your questions are meant to spark joy and provide entertainment. Have some fun with it!

Word balloon that says "LOL"

Using humor can make a hard quiz enjoyable for someone who doesn’t know the answers. If a player knows the answer, that’s great. But if you can make them laugh, that’s a success!

It’s Made for an Audience

Even the toughest question should still keep your audience in mind. If you want to stump your audience, ask a tough question within the topic of the trivia night. You don’t pose a question about movies during a boxing quiz. 

Whether you’re writing your questions from scratch or importing them from a website, don’t choose questions for yourself. We all have our preferences, but they’re often not in line with the theme of the night. Put your audience first.

Always Keep an Eye Out for New Trivia

You can come across an interesting piece of trivia on the street, at work, in the shower, at a friend’s house, and in a number of other places. Always be ready to jot down any interesting fact that you can later form a question about. Inspiration likes to play by its own rules, so don’t expect it to come when you’re sitting at your desk, frantically trying to come up with questions.

Of course, that’s not all! There is so much more to writing an excellent and difficult trivia question, but I bet you’re dying to move on to the actual questions. Before we do that, here are some more tips for you before you are ready to conquer the world of tough trivia!

  • Involve your audience in the question. If you relate the question to your players, they will likely pay closer attention to the game.
  • If you’re using multiple choice questions, make sure all answers are indisputably wrong except for one.
  • Stay consistent. Prior to the game, decide what qualifies as correct. That applies to names, for example. Will you accept someone’s first name, or do you need their last name too? Will you accept just the name that person goes by?
  • Trick questions can be fun if they are incredibly well phrased and you are confident in your audience. In the opposite case, you will look ridiculous.
Neon TV that says "Quiz Time" on it

Quiz: 100 Tough Trivia Questions Designed to Stump You

1. What ‘fruity’ term for a small and unstable country dependent on agriculture was first used by O. Henry in reference to Honduras?

Show Answer

Banana republic “Republic” in his time was often a euphemism for a dictatorship, while “banana” implied an easy reliance on basic agriculture and backwardness in the development of modern industrial technology.

2. Olympic Question: Who won seven gold medals all with world records in the swimming pool at the 1972 Munich Games?

Show Answer

Mark Spitz

Statue of the Olympic rings.

3. Which golfer announced he was leaving his wife and three children for Brenna Cepalak in 1996?

Show Answer

Nick Faldo

4. The Rock, is the nickname of which US federal prison that opened in 1934?

Show Answer

Alcatraz

5.On which record label did Elvis Presley record his first song?

Show Answer

Sun Records

6. What famous novel provided the basic story line for Francis Ford Coppola’s 1979 Vietnam war film epic, Apocalypse Now?

Show Answer

The Heart of Darkness by Joseph Conrad, published in 1902 and set in Africa.

7. Which director of Schindler’s List and E.T. was the most commercially successful cinema director of the 20th century?

Show Answer

Steven Spielberg

8. Who composed the foreboding soundtrack music for the 1975 film Jaws?

Show Answer

John Williams

Illustration of a shark.

9. What’s the desert bird cartoon character Wile E. Coyote’s always trying to catch?

Show Answer

The roadrunner

10. In 1986, actor Paul Newman played the character called Fast Eddie Felson. What was the film?

Show Answer

The Color of Money

11. Which two US cities are joined by Route 66?

Show Answer

Chicago and Los Angeles

A photo of Route 66

12. Which liner built in 1936 became a floating hotel in Long Beach, California?

Show Answer

The Queen Mary

13. The name of which American sports team has its origin in how the fans avoided getting knocked down by trolleys on their way to the games?

Show Answer

Brooklyn Dodgers

14. Which model of Ford car is also the name given to a soft mild breeze?

Show Answer

Zephyr

15. On the hit TV sitcom Seinfeld, what role did Kramer land on the Murphy Brown show when he moved to Hollywood to pursue an acting career?

Show Answer

He played one of Murphy’s many short-term secretaries. Kramer is played by Michael Richards.

16. What was the name of the “girl with kaleidoscope eyes” in a Beatles song?

Show Answer

Lucy

Graffiti of the Beatles.

17. What was the USA’s biggest attack of the Vietnam War when it took place in February 1967?

Show Answer

Operation Junction City

18. Which is the odd one out: Lucifer, Felix, Sylvester and Snowbell?

Show Answer

Snowbell is a real cat in the Stuart Little films. The others are cartoon cats.

19. Whose trumpet was recognizable by the way it was bent out of shape?

Show Answer

Dizzy Gillespie

20. What was the name of Ernest Shackleton’s ship which became stuck in Antarctic ice in 1915?

Show Answer

HMS Endurance

21. What was the name of the pig leader in George Orwell’s Animal Farm?

Show Answer

Napoleon

22. In 1983 what became the first quiz show to be aired daily in Britain?

Show Answer

Blockbusters

23. Which Japanese island that has its capital at Sapporo is the traditional home of the Ainu people?

Show Answer

Hokkaido

24. The most widely accepted explanation for the origin of which symbol is that it is the result of the evolution of the Spanish and Mexican scribal abbreviation for pesos?

Show Answer

The $ symbol

25. Christmas is the biggest candy-selling season in the U.S. What holiday ranks second?

Show Answer

Easter, which surpasses Valentine’s Day, Mother’s Day, and Halloween.

Assorted-color candies.

26. Rice-Kellogg invented what in 1924?

Show Answer

Loudspeakers

27. Name the test applied to computers to see if they can think?

Show Answer

Turing test

28. The neutered male of which animal is known as a barrow?

Show Answer

Pig

29. The English nurse Edith Cavell was executed by the Germans, for being a spy, but was it in the First or Second World War?

Show Answer

World War I (1915)

30. What famous country singer is the subject of more than a dozen musical tributes, including “Singing Teacher,” “The Long Gone Lonesome Blues,” “Midnight in Montgomery,” and “The Ride”?

Show Answer

Hank Williams. The titles of most of the other tributes mention him by name.

31. Unravel the anagram to identify the pop group…. SQUATS OUT

Show Answer

Status Quo

32. Who featured on a number one hit in 1965 and went on to become the Mayor of Palm Springs?

Show Answer

Sonny Bono

33. Can you name the original 5 MTV VJs?

Show Answer

Martha Quinn, J.J. Jackson, Mark Goodman, Alan Hunter, and Nina Blackwood

34. What American film classic did actor John Wayne call “the most un-American thing I’ve ever seen in my whole life”?

Show Answer

The 1952 Gary Cooper western High Noon. Wayne’s objection: “The last thing in the picture is ole Coop putting the United States marshal’s badge under his foot and stepping on it.

35. In which film did Elvis Presley play the character of Lucky Jackson?

Show Answer

Viva Las Vegas

36. Who played the role of Robin in the ’60s television version of Batman?

Show Answer

Burt Ward

37. In the Stephen King book IT, what is “IT” before it becomes a monster?

Show Answer

A clown

38. Which director connects the films The Color Of Money, The Last Waltz, and King Of Comedy?

Show Answer

Martin Scorcese

39. According to the traditional rhyme, a child born on which day is said to be ‘full of grace’?

Show Answer

Tuesday

40. Icicle Works had a hit with “Love is a Wonderful Colour” or “It’s a Wonderful Life”?

Show Answer

“Love is a Wonderful Colour”

41. Which game was first patented under the name “Spharistrike”?

Show Answer

Lawn tennis

42. Which sport event combines riding, revolver, shooting, fencing, swimming, and running?

Show Answer

The pentathlon

43. On which real-life person was Terence Rattigan’s Ross based?

Show Answer

Lawrence of Arabia

44. The US eats the most ice cream per capita. Which country takes second place?

Show Answer

New Zealand

45. Who did Mike Tyson defeat when he first won the WBC world heavyweight title at the age of 20?

Show Answer

Trevor Berbiek

46. Which female singing voice lies between soprano and contralto?

Show Answer

Mezzo-soprano

47. The Colossus of Rhodes was a statue of who?

Show Answer

Helios the Sun God

48. Which sport has the most umpires per player?

Show Answer

Tennis (15-1)

49. When Elizabeth Cochrane traveled around the world in less than 80 days in 1890, she used another name to conceal her identity. What was it?

Show Answer

Nellie Bly

50. Who did a striker named Pauletta score a hat trick against in Poland in 2002 World Cup?

Show Answer

Portugal

51. Which famous Italian director was murdered in November 1975?

Show Answer

Pier Paolo Pasolini

52. What first appeared on British streets on the 27th of June 1967, was it a cash point machine, a green man pedestrian crossing, or the Mini car?

Show Answer

A cash point machine

53. How many weeks does it take the human body to totally shed & replace its outer layer of skin?

Show Answer

4 weeks

54. Which medieval Islamic dynasty was founded in 1250 in Egypt and Syria by slave soldiers who deposed the Ayyubids?

Show Answer

The Mamluks In 1291 they drove the last Crusaders from Palestine. Their reign is divided into a “Bahri” period from 1250-1382 and a “Circassian” period from 1382-1517. They were defeated by the Ottomans, who conquered Egypt in 1517.

55. Which future First Lady had walk-on parts in Becky Sharp and Small Town Girl in the ’30s?

Show Answer

56. During the 20th Century, which British Prime Minister and American President have shared the same surname?

Show Answer

Wilson – Woodrow and Harold

57. Which US gangster played on the big screen by Robert De Niro, was finally jailed for tax evasion?

Show Answer

Al Capone

58. Who has the best won-lost percentage of any pitcher with 15 or more wins against the New York Yankees?

Show Answer

Vintage baseball.

59. What gorge in the Ngorongoro area of Tanzania is considered the seat of humanity after the discovery of the earliest known specimens of modern man?

Show Answer

The Olduvai Gorge It is one of the most important prehistoric sites in the world and has been instrumental in furthering understanding of early human evolution. Excavation work there was pioneered by Louis Leakey in the 1950s and is continued today by his family.

60. Which word could mean either a piece of coal, a horse, a swan, or a bread roll?

Show Answer

Cob

61. Who was the first poet to be buried in Poets Corner in London’s Westminster Abbey?

Show Answer

Geoffrey Chaucer

62. Dr. Henry Jones, Jr. (born July 1, 1899) is a fictional professor, archaeologist, and adventurer who is better known by what nickname?

Show Answer

Indiana

63. Which epic 1960s film is unique in the sense that the only female featured in the entire film is a camel named Gladys?

Show Answer

Lawrence of Arabia. It is unique in being the only film to win the Best Film award without containing a single female speaking role.

64. The Trưng Sisters who successfully rebelled against the Chinese Han-Dynasty in the 1st century AD are regarded as national heroines in which country?

Show Answer

Vietnam They led the first resistance movement against the occupying Chinese after 247 years of domination. Many temples are dedicated to them, and a yearly holiday, occurring in February, to commemorate their deaths is observed by many Vietnamese.

65. In the film The Russians Are Coming, the Russians Are Coming, what role did Alan Arkin play? (Clue: he won an Academy Award in 1966 for the role.)

Show Answer

Lt Rozanov

66. Which former heavyweight boxing champion has an identical twin brother called George?

Show Answer

Henry Cooper

67. In the world of music, how is “Saul Hudson” more commonly known?

Show Answer

Slash/Guns n Roses

68. Who’s the lead vocalist for the band The Spencer Davis Group, Traffic, Go, Blind Faith?

Show Answer

Steve Winwood

69. Who did former communist Aleksander Kwasniewski defeat in a 1995 Eastern European presidential election?

Show Answer

Lech Walesa

70. In the cartoon show My Pet Monster, what were the only things that could send Beastor, Monster’s enemy, back to the Monster World?

Show Answer

A pair of orange handcuffs

71. In how many categories was the 1997 film Titanic nominated for an Oscar?

Show Answer

Fourteen categories, winning eleven

Closeup of a large ship.

72. How many years was Satan tied up in chains for according to the Book of Revelations?

Show Answer

1000

73. Robert Redford was paid $6 million for his role in the 1985 film Out of Africa. How much was leading lady Meryl Streep paid?

Show Answer

$3 million

74. In 1956, actor James Dean (posthumous nomination) played the character called Jett Rink, what was the film?

Show Answer

Giant

75. According to the song made famous by Judy Garland, who lives at 5133 Kensington Avenue?

Show Answer

The boy next door

76. Brian Jones died in a swimming pool at Cotchford Farm, Sussex, but which author once owned the farm?

Show Answer

A A Milne (Winnie The Pooh)

77. In which Hyde Park lake do members of a local swimming club take a traditional Christmas Day dip?

Show Answer

Serpentine

78. Which street in New York’s Manhattan district is famous for its theatres?

Show Answer

Broadway

79. What is the name given to someone who studies plants?

Show Answer

Botanist

Female florist in flower shop.

80. Although never part of international maritime law, which phrase was popularised by its usage on the RMS Titanic as a consequence of which 74% of the women and 52% of the children were saved but only 20% of the men?

Show Answer

Women and children first The practice arose from the chivalrous actions of soldiers during sinking of HMS Birkenhead in 1852, though the phrase was not coined until 1860.

81. Which chart topping female singer with a 4 letter name was born Rosemary Scallion?

Show Answer

Dana

82. ‘I am become Death, the shatterer of Worlds.’ This quote from the Bhagavad Gita was famously used at what specific 1945 event?

Show Answer

Trinity (nuclear test)

83. What singer is honored by San Francisco’s Hello, Gorgeous!! museum, that sells wigs and fake noses to visitors who want to look just like her?

Show Answer

Barbra Streisand

84. What is the name of the soul star who resigned from his role as chef in South Park due to the show’s mocking of religion?

Show Answer

Isaac Hayes

85. What was Britain’s most famous fighter plane during World War II?

Show Answer

Spitfire

86. The name of which spice also known as Jamaica pepper was coined by people who thought that it combined the flavour of cinnamon, nutmeg and cloves?

Show Answer

Allspice

87. An unnamed person in America is called John Doe, what is an unnamed person called in England?

Show Answer

John Smith

88. Who said “This is a dangerous and uncertain world” hours before his assassination?

Show Answer

John F. Kennedy

89. Which was the first British sitcom to win the best comedy prize at the Golden Globe Awards?

Show Answer

The Office (2004)

90. What is the trade name for the non-stick material used for coating cooking pans?

Show Answer

Teflon

91. Name the TV family that lives at the following address: 565 North Clinton Drive, Milwaukee

Show Answer

The Cunninghams in Happy Days

92. Until the introduction of the Euro, what is the unit of currency in Austria?

Show Answer

Schilling

93. What do Shirley Bassey, Sheena Easton, and Duran Duran have in common?

Show Answer

They all recorded James Bond themes

94. What famous child star failed her screen test for a part in the Our Gang movie comedies?

Show Answer

Shirley Temple

95. What southwestern U.S. state has the highest percentage of non-English speakers?

Show Answer

New Mexico

96. Scud East was the eponymous hero’s friend in which famous 19th Century novel?

Show Answer

Tom Brown’s Schooldays

97. What work of the 17th century Dutch painter Johannes Vermeer is called ‘the Mona Lisa of the North’ or ‘the Dutch Mona Lisa’?

Show Answer

Girl with a Pearl Earring

98. What football club did Gordon Banks play for when he won his 1966 World Cup Medal?

Show Answer

Leicester City

99. In which film does Marilyn Monroe’s character say she keeps her underwear in the ice-box?

Show Answer

The Seven-Year Itch

Drawing of Marilyn Monroe

100. In 1998 who did Vanity Fair describe as “simply the world’s biggest heart throb?”

Show Answer

Leonardo DiCaprio

Questions for the People!

Quizmasters like to focus on the challenging aspect of a tough question, and often forget about the entertainment element. At the end of the day, the purpose of trivia is entertainment. Sure, you want to impress your friends and show off your knowledge, but it’s all completely worthless if you don’t have fun. Write questions for the people! Don’t bother with questions that nobody can answer; your audience will get bored.

Hopefully, you’ve learned a thing or two about tough questions today. The most valuable lesson is: Don’t be afraid of easy questions, be afraid of poorly written and confusing ones! A good easy question is still better than an obscure trivia question nobody can answer. 

Lit up question mark sign

What do you think about the topic? Do you prefer tough questions? How many of our questions did you manage to answer? Let us know in the comments!

Filed Under: Quizzes, Trivia Nights Tagged With: questions and answers, quiz, tough trivia questions, trivia questions

Anastasia Voloshina

About Anastasia Voloshina

Anastasia Voloshina is a professional writer, editor, and trivia enthusiast. With an extensive background in trivia writing, Anastasia has developed a deep understanding of what it takes to run a successful game night. Anastasia got her Marketing degree in a university in Prague, where she also took writing classes.

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