
Surely, in the years of asking and answering trivia questions, you’ve come across some that just have that extra jazz (heck, we even have a guide on how to make ones just like that). 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!

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.
(But if you are someone who loves numbers, we do have a list of trivia questions where the answers can be numbers, too.)

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!

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.

Quiz: 100 Tough Trivia Questions Designed to Stump You

3. Which golfer announced he was leaving his wife and three children for Brenna Cepalak in 1996?
4. The Rock, is the nickname of which US federal prison that opened in 1934?
5.On which record label did Elvis Presley record his first song?
8. Who composed the foreboding soundtrack music for the 1975 film Jaws?

9. What’s the desert bird cartoon character Wile E. Coyote’s always trying to catch?
10. In 1986, actor Paul Newman played the character called Fast Eddie Felson. What was the film?
11. Which two US cities are joined by Route 66?

12. Which liner built in 1936 became a floating hotel in Long Beach, California?
14. Which model of Ford car is also the name given to a soft mild breeze?
16. What was the name of the “girl with kaleidoscope eyes” in a Beatles song?

17. What was the USA’s biggest attack of the Vietnam War when it took place in February 1967?
18. Which is the odd one out: Lucifer, Felix, Sylvester and Snowbell?
19. Whose trumpet was recognizable by the way it was bent out of shape?
20. What was the name of Ernest Shackleton’s ship which became stuck in Antarctic ice in 1915?
21. What was the name of the pig leader in George Orwell’s Animal Farm?
22. In 1983 what became the first quiz show to be aired daily in Britain?
23. Which Japanese island that has its capital at Sapporo is the traditional home of the Ainu people?
25. Christmas is the biggest candy-selling season in the U.S. What holiday ranks second?

26. Rice-Kellogg invented what in 1924?
27. Name the test applied to computers to see if they can think?
28. The neutered male of which animal is known as a barrow?
31. Unravel the anagram to identify the pop group…. SQUATS OUT
32. Who featured on a number one hit in 1965 and went on to become the Mayor of Palm Springs?
33. Can you name the original 5 MTV VJs?
35. In which film did Elvis Presley play the character of Lucky Jackson?
36. Who played the role of Robin in the ’60s television version of Batman?
37. In the Stephen King book IT, what is “IT” before it becomes a monster?
38. Which director connects the films The Color Of Money, The Last Waltz, and King Of Comedy?
39. According to the traditional rhyme, a child born on which day is said to be ‘full of grace’?
40. Icicle Works had a hit with “Love is a Wonderful Colour” or “It’s a Wonderful Life”?
41. Which game was first patented under the name “Spharistrike”?
42. Which sport event combines riding, revolver, shooting, fencing, swimming, and running?
43. On which real-life person was Terence Rattigan’s Ross based?
44. The US eats the most ice cream per capita. Which country takes second place?
45. Who did Mike Tyson defeat when he first won the WBC world heavyweight title at the age of 20?
46. Which female singing voice lies between soprano and contralto?
47. The Colossus of Rhodes was a statue of who?
48. Which sport has the most umpires per player?
50. Who did a striker named Pauletta score a hat trick against in Poland in 2002 World Cup?
51. Which famous Italian director was murdered in November 1975?
53. How many weeks does it take the human body to totally shed & replace its outer layer of skin?
55. Which future First Lady had walk-on parts in Becky Sharp and Small Town Girl in the ’30s?
57. Which US gangster played on the big screen by Robert De Niro, was finally jailed for tax evasion?
60. Which word could mean either a piece of coal, a horse, a swan, or a bread roll?
61. Who was the first poet to be buried in Poets Corner in London’s Westminster Abbey?
66. Which former heavyweight boxing champion has an identical twin brother called George?
67. In the world of music, how is “Saul Hudson” more commonly known?
68. Who’s the lead vocalist for the band The Spencer Davis Group, Traffic, Go, Blind Faith?
71. In how many categories was the 1997 film Titanic nominated for an Oscar?

72. How many years was Satan tied up in chains for according to the Book of Revelations?
75. According to the song made famous by Judy Garland, who lives at 5133 Kensington Avenue?
76. Brian Jones died in a swimming pool at Cotchford Farm, Sussex, but which author once owned the farm?
77. In which Hyde Park lake do members of a local swimming club take a traditional Christmas Day dip?
78. Which street in New York’s Manhattan district is famous for its theatres?
79. What is the name given to someone who studies plants?

81. Which chart topping female singer with a 4 letter name was born Rosemary Scallion?
85. What was Britain’s most famous fighter plane during World War II?
87. An unnamed person in America is called John Doe, what is an unnamed person called in England?
88. Who said “This is a dangerous and uncertain world” hours before his assassination?
89. Which was the first British sitcom to win the best comedy prize at the Golden Globe Awards?
90. What is the trade name for the non-stick material used for coating cooking pans?
91. Name the TV family that lives at the following address: 565 North Clinton Drive, Milwaukee
92. Until the introduction of the Euro, what is the unit of currency in Austria?
93. What do Shirley Bassey, Sheena Easton, and Duran Duran have in common?
94. What famous child star failed her screen test for a part in the Our Gang movie comedies?
95. What southwestern U.S. state has the highest percentage of non-English speakers?
96. Scud East was the eponymous hero’s friend in which famous 19th Century novel?
98. What football club did Gordon Banks play for when he won his 1966 World Cup Medal?
99. In which film does Marilyn Monroe’s character say she keeps her underwear in the ice-box?

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

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!
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