100 Hard Trivia Questions That Will Stump You (2024 List)

Updated Date:
January 4, 2024
Which companies play trivia with their co-workers every week?
lyft logo
amazon logonike logoimpossible logo

Hard trivia questions are some of the best around. Whether you're looking to be challenged yourself or you want difficult questions to share with others, we've got the list for you.

We've gone ahead and broken down these tough trivia questions into four levels of difficulty:

  • Hard
  • Harder
  • Very Hard
  • Impossible

That way, no matter what level you're looking for you'll be able to find 25 questions that should suit your fancy. Good luck! You're gonna need it!

100 Hard Trivia Questions (Updated for 2024)

Hard Trivia

  1. After she became Princess of Monaco in 1956, she used the bag to hide her growing belly while pregnant with her first child, Princess Caroline. That's the origin of the name of an Hermès bag named for what former actress?

    Answer: Grace Kelly

  2. What technology company was founded in 1993 with the vision that the next wave of computing would be graphics-based? The company took its name from the Latin word for "envy" and features product families GeForce, Quadro, and Tegra.

    Answer: Nvidia

  3. Daniel Powter is a Canadian singer-songwriter that rose to fame as his song spent five weeks atop the Billboard charts in 2005. The song featured prominently in video montages of American Idol contestants who were eliminated from the show. What was Powter's two-word smash hit?

    Answer: Bad Day

  4. A boy from "The Adventures of Rocky and Bullwinkle and Friends," the namesake character of a certain "Lagoon" comic strip, the battle-hardened World War II M4 tank, and the nutty scientist in "The Klumps" all share what name?

    Answer: Sherman

  5. In logical argument and mathematical proof, a symbol consisting of three dots placed to form an upright triangle is used to represents which word?

    Answer: Therefore

  6. The world capital cities of Vienna, Bratislava, and Budapest all lie along what river, the second-longest in Europe?

    Answer: Danube

  7. The United Nations General Assembly adopted a historic document (Resolution 217) in Paris at its third session in 1948. The document is regularly abbreviated as UDHR, which stands for what?

    Answer: Universal Declaration of Human Rights

  8. Which two months of the year are named for mortal men?

    Answer: July and August

  9. Who is the only singer to win the Grammy Awards for Album, Record, and Song of the Year twice? Both of the winning albums had titles that were two-digit numbers.

    Answer: Adele

  10. What is the name for a type of rigid airship named for its German inventor that were first flown commercially in 1910 and carried tens of thousands of fare-paying passengers before World War I slowed down the airship business?

    Answer: Zeppelin

  11. What highly sought-after item of the modern age was created anonymously under the pseudonym Satoshi Nakamoto?

    Answer: Bitcoin

  12. What classic literary villain, described as a "Machiavellian schemer and manipulator" shares his name with an avian sidekick in the Disney film "Aladdin?"


    Answer: Iago

  13. What is the metric unit, consisting of 10,000 square meters, that is the primary measure of land in most countries?

    Answer: Hectare

  14. In 2022, the U.S. Treasury minted landmark quarters featuring what "I Know Why the Caged Bird Sings" author?

    Answer: Maya Angelou

  15. TV producer and writer Adam F. Goldberg cut his teeth on "Aliens in America" and "Community" before launching what very guessable autobiographical sitcom based on his Philadelphia childhood?

    Answer: The Goldbergs

  16. Established by President John F. Kennedy in 1963, Elvis Presley, Babe Ruth, Tiger Woods and Rush Limbaugh received what prestigious medal by President Donald Trump during his presidential term?

    Answer: Presidential Medal of Freedom

  17. What word completes the following Santana lyric? This word is also the title of the song. "You got the kind of loving that can be so ______, yeah. / Gimme your heart, make it real / Or else forget about it."

    Answer: Smooth

  18. El Prat airport is located in which city on the Mediterranean Sea, which held the 1992 Summer Olympics?

    Answer: Barcelona

  19. What is the common name of the object that is formerly known as a besom, has a common association with Halloween, and is produced and sold by brands such as Treelen, Libman, and SWOPT?

    Answer: Broom

  20. Deglutition is the scientific term for what common bodily function that humans do hundreds of times a day?

    Answer: Swallowing

  21. What well-known artist famously severed part of Vincent Van Gogh's left ear? Note: although there has been speculation in recent years that it was *actually* Paul Gauguin, we are going to stick with the most commonly-accepted perpetrator by art historians.

    Answer: Vincent Van Gogh

  22. What famed Chicago-based improv theater group served as a career springboard for Steve Carell, Tina Fey, John Candy, and more?

    Answer: Second City

  23. Although the term was initially coined on the London Stock Exchange in the 18th century for a stockbroker who defaulted on his debts, it's now commonly used to refer to office-holders headed out the door. What is this fowl two-word term?

    Answer: Lame duck

  24. According to an urban legend, what type of animal caused the Great Chicago Fire of 1871 by knocking over a lantern?

    Answer: Cow

  25. A lion holding a sword appears on the logo of Ceylon Tea as well as the flag of what teardrop-shaped Indian Ocean country that exports the product?

    Answer: Sri Lanka

Harder Trivia

  1. Throughout the Harry Potter novels, Harry is mentioned by name 18,956 times. Which character is the second most mentioned coming in at a total of 6,464?

    Answer: Ron Weasley

  2. What two one-syllable rhyming words summarize the following phrase? To handily defeat the protagonist of "To Kill a Mockingbird."

    Answer: Rout Scout

  3. Name the only person to be a United States President and Supreme Court Justice. He was even Chief Justice! He was the 27th president and the tenth chief justice.

    Answer: Taft

  4. What "G" instrument is technically a metallophone because its set of tuned keys are made of metal plates or tubes rather than the wood of a xylophone? The instrument was featured famously in many Rush songs such as "The Spirit of Radio" and "Closer to the Heart."

    Answer: Glockenspiel

  5. One of the world's largest construction projects, Al Maktoum AKA Dubai World Central is what kind of go-go piece of infrastructure?

    Answer: Airport

  6. Played by Frank Sinatra in a film version, Nathan Detroit is a gambling boss in what classic 1950s Broadway musical?

    Answer: Guys and Dolls

  7. In what country was Haagen-Dazs ice cream developed?

    Answer: The United States

  8. What famed children's author said the following? "I answer all my children's letters "sometimes very hastily" but this one I lingered over. I sent him a card and I drew a picture of a Wild Thing on it. I wrote, 'Dear Jim: I loved your card.' Then I got a letter back from his mother and she said: 'Jim loved your card so much he ate it.' That to me was one of the highest compliments I've ever received."

    Answer: Maurice Sendak

  9. What is the name of the single-player sliding block puzzle game designed by Italian web developer Gabriele Cirulli in which a smartphone user tries to create a certain value by sliding and combining tiles around a grid?

    Answer: 2048

  10. More than 500 million of the Flying Pigeon PA-02 bicycles have been made, many multiples more than the next-most popular model of bicycle. The Flying Pigeon brand has been state-owned since the mid 20th century by what country?

    Answer: China

  11. What was the name of the commission established to investigate the JFK assassination?

    Answer: Warren Commission

  12. Ted Lasso liked it so much he saw it twice: Upon a time (2007 to be exact), Glen Hansard and Markéta Irglová won a Best Original Song Oscar for "Falling Slowly," from what film about struggling Dublin musicians?

    Answer: Once

  13. In what Fox teen drama series did character Seth Cohen claim to have invented the holiday of Chrismukkah?

    Answer: The O.C.

  14. Looking to stimulate a stagnant Soviet economy in the '80s, Mikhail Gorbachev introduced what P-word political movement that's just Russian for "reconstruction" or "restructuring"?

    Answer: Perestroika

  15. What does SMS stand for in the context of cellular communications?

    Answer: Short Message Service

  16. Netball, water polo, and Olympic rugby are all played with how many players per team?

    Answer: Seven

  17. What is the name of the private, all-male HBCU (Historically Black Colleges and Universities) located in Atlanta, Georgia which is the largest men's liberal arts college in the U.S. and is the alma matter of Martin Luther King Jr., Spike Lee and Edwin Moses?

    Answer: Morehouse College

  18. All Mughal emperors were practitioners of what religion? The empire's peak is often considered the 17th and 18th century when it ruled over nearly all of the Indian subcontinent.

    Answer: Islam

  19. Only one of the seven countries that borders India has a population with less than one million people. This country famously measures "gross national happiness" and has Thimphu as its capital city. What is this country?

    Answer: Bhutan

  20. What 110-mile-per-hour air currents circle Earth's tropopause in a westerly direction?

    Answer: Jet stream

  21. Take two words and arrange them one way, you get a Canadian whisky. Arrange them the other way and you get a generic soda brand. What are the two words?

    Answer: Crown Royal

  22. What man was the running mate of Lyndon B. Johnson in 1964? This man's initials are famously H.H.H.

    Answer: Hubert Horatio Humphrey Jr

  23. After Chicago, what is the most populous U.S. city in the Central Time Zone? Hint: They're about 1,000 miles apart from each other.

    Answer: Houston

  24. The first McDonald's restaurant was opened in what state? We're talking about the very first McDonald's, not the first franchise location.

    Answer: California

  25. There is a very small (180 square miles) landlocked sovereign country between France and Spain with a population of approximately 75,000. Believed to have been created by Charlemagne, what is the name of this country?

    Answer: Andorra

Very Hard Trivia

  1. If you were to combine words meaning 'the day before' and 'to cease work,' you'd find yourself at what notable world landmark?

    Answer: Everest (Eve / Rest)

  2. What renowned non-fiction author and journalist detailed the horrific crimes committed by Mormon Fundamentalist brothers Ron and Dan Lafferty in "Under the Banner of Heaven?"

    Answer: Jon Krakauer

  3. The Year of Magical Thinking and "Slouching Toward Bethlehem" are works by what Pulitzer-nominated, Sacramento-raised journalist?

    Answer: Joan Didion

  4. What is the animal term associated with some lip gloss applicators? The name does not come from the fuzzy tip resembling fur, but rather from the hoof-shaped, angular tip of the applicator.

    Answer: Doe foot

  5. When ignoring the stem, how many points does the maple leaf on the Canadian flag have?

    Answer: 11

  6. She made her fortune by developing and marketing cosmetics and hair care products for black women. She's also listed as the first female self-made millionaire in America in the Guinness Book of World Records. Who is this woman?

    Answer: Madam C. J. Walker

  7. 1987 was the first time in 13 years that what American woman did not win a tennis Grand Slam event?

    Answer: Chris Evert

  8. Artist Berthe Morisot gets her lean on in "The Repose," an oil by what other French Impressionist painter?

    Answer: Edouard Manet

  9. With 158 separate stanzas, this nation is often considered to have the longest national anthem in the world. What is this European country with a population of approximately 11 million?

    Answer: Greece

  10. James Dean wore a cowboy hat and got slathered in oil in what epic 1956 film that earned him his second and final Oscar nomination?

    Answer: Giant

  11. What eight-letter word precedes "Struggle" and "Imperium" in the names of board games about the Cold War and space conquest, respectively?

    Answer: Twilight

  12. There's a town in the Peloponnese region of Greece with a namesake food item known for its purple color and smooth meaty texture. What is this fruit?

    Answer: Kalamata Olive

  13. The three smallest bones in the human body are in the ear. They are the stapes, the incus, and what other hammer-like ossicle?

    Answer: Malleus

  14. Militia Company of District II under the Command of Captain Frans Banninck Cocq is the official name of a 1642 painting by Rembrandt van Rijn, but the Amsterdam-located painting is more often known by what shortened name?

    Answer: The Night Watch

  15. It's most commonly known today as a "hashtag" or "pound sign," but what is the technical "O" term for this widespread symbol?

    Answer: Octothorpe

  16. Economist George Akerlof's famous 1970 paper "The Market for ______" brought issues such as information asymmetry to the forefront of economics. What word fills the blank in Akerlof's theory?

    Answer: Lemons

  17. Outside of Silverado Building Materials and Nursery in Sacramento stands a 25-foot-tall wooden statue of what actor's likeness who played the gun-slinging Jake in the 1985 western film "Silverado"?

    Answer: Kevin Costner

  18. The Sun is (of course) the closest star to Earth. What star is the next closest? It's slightly closer than the similarly-named Alpha Centauri A.

    Answer: Proxima Centauri

  19. The most famous work of what Roman poet born in 43 BC begins "My intention is to tell of bodies changed to different forms?"

    Answer: Ovid

  20. Is the father Mark Darcy or new flame Jack? So goes the plot of what 2016 movie sequel?

    Answer: Bridget Jones's Baby

  21. In 1756, Voltaire claimed that none of the three words in what influential political entity's name were accurate?

    Answer: Holy Roman Empire

  22. One of South Africa's three capital cities is in the northern part of Gauteng province, straddles the Apies River, and contains the foothills of the Magaliesberg mountains. What city is this?

    Answer: Pretoria

  23. What 13-letter German loanword means a novel that focuses on the psychological and personal growth of the protagonist from youth to adulthood?

    Answer: Bildungsroman

  24. What frequently-misnomered mammal has fingerprints so indistinguishable from humans that they have occasionally been wrongfully collected as evidence at crime scenes?

    Answer: Koalas

  25. The fight over teaching evolution in classrooms went to court in 1925 for the famous Scopes Trial. Who argued for the prosecution against John Scopes? This famous lawyer's other hot-button issue was the gold standard.

    Answer: William Jennings Bryan

Impossible Trivia

  1. What cubist's work, featuring outlines of birds, was the first piece by a living artist to adorn the Louvre? It covered the ceiling of what was once King Henri II's antechamber and caused an uproar in Paris.

    Answer: Georges Braque

  2. What color, aside from their black trim, were the original Converse All-Stars Chuck Taylor basketball shoes when they were first produced in 1917?

    Answer: Brown

  3. The world's smallest capital city, Ngerulmud, has a population of only approximately 400. What country is home to Ngerulmud?

    Answer: Palau

  4. Solar energy inventor and pioneer Frank Shuman wrote the following in the New York Times in what decade? "We have proved ... that after our stores of oil and coal are exhausted the human race can receive unlimited power from the rays of the Sun."

    Answer: 1910s

  5. The circumlocution office is a government department satirized in which of Charles Dickens' works, whose titular character has the first name Amy?

    Answer: Little Dorrit

  6. Hailed as the "original soul sister" and the "godmother of rock and roll" because of her pioneering guitar techniques, Sister Rosetta Tharpe was born in which southern state to two cotton pickers in 1915?

    Answer: Arkansas

  7. In an effort to address (albeit in a small way) a public health crisis, the Google ______ Indicator, sponsored by the Indian Ministry of Urban Development was integrated into Google Maps in India in 2016. What word fills in the blank?

    Answer: Toilet

  8. February, don't put that in your mouth!! According to Social Security data from 2021, what was the most popular baby name that shares a name with one of the 12 months of the year?

    Answer: August

  9. According to the Organization for Economic Cooperation and Development, what is the most educated country on the planet as of 2019? To measure this, they are ranking countries based on the share of adult residents between the ages of 25 and 64 with a "tertiary education," meaning a two-year or four-year degree or education via vocational program. The leader had ~56% of the population with tertiary education.

    Answer: Canada

  10. Floria is the first name of what titular Puccini opera heroine, who is herself an opera singer?

    Answer: Tosca

  11. Inspired by her new Dewey Decimal knowledge, Parker Posey's character rearranges her DJ roommates vinyl collection in what 1995 coming-of-age library-slash-fiesta movie?

    Answer: Party Girl

  12. U.S. Secretary of Commerce Harry Hopkins helped conceive what New Deal public works program that produced the Tennessee Valley Authority and Federal Theatre Project?

    Answer: Works Progress Administration / WPA

  13. In 1965, "Turn, Turn, Turn" by The Byrds reached #1 on the Billboard Hot 100. In 1983 and 1999, two other songs whose title is a word repeated three times reached #1. Name one of them.

    Answer: Bills, Bills, Bills or Say, Say, Say

  14. In the brewing process, wort contains the amino acids that provide what lucky, rich element to the yeast?

    Answer: Nitrogen

  15. Larry "Doc" Sportello is the pot-smoking private investigator protagonist of what 2009 Thomas Pynchon novel that was adapted into a film by director Paul Thomas Anderson?

    Answer: Inherent Vice

  16. A demonstration sport at the 1988 and 1992 Winter Olympics was which form of skiing very similar to figure skating, combining spins, jumps, and flips in a two-minute routine choreographed to music?

    Answer: Ski ballet

  17. Informally known as "The God of Cricket," what former Indian cricketer is widely regarded as one of the greatest batsmen in the history of the sport and is the highest run-scorer of all time in international competition?

    Answer: Sachin Tendulkar

  18. CERN hosts the Large Hadron Collider, the world's highest energy particle collider which opened underneath the Swiss-French border in 2008. The LHC surpassed the prior record-holding particle accelerator in what U.S. state?

    Answer: Illinois

  19. Calvinism is a branch of Protestantism that is most closely associated with what European country? The association arises from the fact that most early ministers were taught in this country.

    Answer: Switzerland

  20. The term "magic bullet" was coined by German scientist Paul Ehrlich to describe a compound that would kill only a specifically targeted organism. Ehrlich even invented the "first magic bullet" with Salvarsan, which was used to treat which disease?

    Answer: Syphillis

  21. What Hapsburg monarch declared Martin Luther to be an outlaw at the Diet of Worms and also divided Hapsburg territory into two parts prior to his abdication just after the Peace of Augsburg?

    Answer: Charles V

  22. Which geological time period that began 358.9 million years ago, during which large coal deposits formed, has a name derived from the Latin for "coal-bearing?"

    Answer: Carboniferous

  23. Around 200 B.C. in Asia there was a technological breakthrough that suddenly made horses much more valuable to the military because of the increased riding stability. What was this invention?

    Answer: Stirrups

  24. The highest volcano outside of South America also doubles as its home continent's highest mountain. In what country is this 19,000-foot peak found?

    Answer: Tanzania

  25. Craigslist is named after its founder. What is Craig's seven-letter two-syllable "N" last name?

    Answer: Newmark

Play Hard Trivia with Water Cooler Trivia

Water Cooler Trivia is well-equipped to provide you with exciting and engaging trivia quizzes.

So, how does it work?

Each week, our team will deliver original trivia quizzes straight to your inbox.

All you have to do is pick the categories.

You can leave the rest of the heavy lifting to us.

Take Water Cooler Trivia for a test run with our four-week free trial.

Is there an error in one of our questions?

We do everything we can to ensure that Water Cooler Trivia's questions are appropriate, relevant, and accurate. Our database has tens of thousands of questions, so we don't always get it right. If you see a question that needs editing, we would love if you let us know here or email [email protected].

Celebrating brains
1,200 companies play Water Cooler Trivia every week
Learn MoreWeekly Trivia For Your Office →