60 Jeopardy! Questions That’ll Leave You Stumped For Good

Do you ever watch Jeopardy? And secretly wonder how you’d fare on the show? 

If you’d like to test your knowledge, this blog post contains 60 tricky questions from actual Jeopardy! Episodes.  

We’ll also go over strategies to up your Jeopardy! Skills, dive into some of the lore of Jeopardy! History, and teach you how to create your questions. 

Who knows, maybe you’re the next Ken Jennings! Only one way to find out. Check out the questions below.

60 Tricky Jeopardy! Questions From Each Difficulty Level

The list below includes actual Jeopardy! Questions spanning from Season 1 in 1984 to Season 39 in 2023. You’ll also find several questions from 2020’s Jeopardy!: The Greatest of All Time.

There are questions from each difficulty category (noting that from 1984 until 2001, question values ranged from $100-$500 in the Jeopardy! Round and $200-$1,000 in the Double Jeopardy! Round. Only from 2001 onward did the prize money double per question. As such, questions from older seasons are scaled to the modern prize money ranking).

Let’s get into it! How is your Jeopardy? Smarts?

$200 Jeopardy! Round questions

1. Category: Museums

Clue: The Vatican has an entire museum devoted to these darn people of ancient Etruria

Answer: The Etruscans

2. Category: American Literature

Clue: Washington Irving’s tale of this farmer who takes a big snooze was based on a German folktale

Answer: Rip Van Winkle

3. Category: Historic Names

Clue: In 1984, this 17th c. Quaker who governed a colony was made an honorary U.S. citizen

Answer: William Penn

4. Category: Historic Sites

Clue: This territory was formally transferred to the U.S. at Castle Hill in Sitka

Answer: Alaska

5. Category: Black America

Clue: York, an expert hunter, accompanied this pair on their 1800s expedition

Answer: Lewis and Clark

$400 Jeopardy! Round questions

6. Category: The 40’s

Clue: This right-wing group was named for the 1st victim of the “Cold War,” killed in China in 1945

Answer: The John Birch Society

7. Category: 3 Letter Words

Clue: Follows drag & hair, precedes work & worth

Answer: Net

8. Category: You Get a “D”

Clue: It’s a calendar or list of the upcoming cases set to be tried at a court

Answer: Docket

9. Category: The Brady Bunch

Clue: ’80s & ’90s Treasury Secretary Nicholas Brady dealt with the crisis & bailout of failing S&Ls, short for these institutions

Answer: Savings & loans

10. Category: Fruit

Clue: Clingstone & freestone are the two main classifications for this fruit, once called a Persian apple

Answer: Peach

$600 Jeopardy! Round questions

11. Category: T.V. Catchphrases by Show

Clue: “Bazinga!”

Answer: The Big Bang Theory

12. Category: Women in Comics

Clue: In 1995, artist & writer John Byrne took over the comic book starring this Amazon princess.

Answer: Wonder Woman

13. Category: A River Runs Under It

Clue: Today buried in tunnels, Moscow’s Neglinnaya river fed the moat protecting this fortress

Answer: The Kremlin

14. Category: We Love “R” Music (music that starts with the letter “R”)

Clue: Aerosmith’s Steven Tyler & Joe Perry joined this rap trio on their 1986 hit “Walk This Way.”

Answer: Run-DMC

15. Category: Abbreviated No. 1 TV Shows

Clue: On N.B.C., 1997-1998: The uproarious “S”

Answer: Seinfeld

$800 Jeopardy! Round questions

16. Category: Strong Men

Clue: Beefy Barry Bonds has hit many balls into the “Cove” named for this earlier Giants slugger

Answer: Willie McCovey

17. Category: We’re Full!

Clue: Your place is really full if you’re packed to these exposed beams in the ceiling

Answer: The rafters

18. Category: Feat of Clay

Clue: On TV & film, he played Tonto’s partner

Answer: Clayton Moore

19. Category: American Literature

Clue: 4 Chinese women meet regularly to play Mah-jongg & to talk about life & their children in this 1989 Amy Tan novel

Answer: The Joy Luck Club

20. Category: Slang

Clue: Homer Simpson asked Bart & Lisa if they wanted to go to Blockoland; their response: this 3-letter word of indifference

Answer: Meh

$1,000 Jeopardy! Round questions

21. Category: Body Parts in Latin

Clue: Genu (as in genuflect)

Answer: The knee

22. Category: UNICEF

Clue: This 1971 George Harrison project has raised over $10 million for UNICEF programs

Answer: The Concert for Bangladesh

23. Category: Sports

Clue: This sport combines cross-country skiing with rifle-shooting skills

Answer: Biathlon

24. Category: Woody Allen

Clue: “I don’t want to achieve immortality through my work. I want to achieve it through not…” Doing this

Answer: Dying

25. Category: Medieval Fashion

Clue: In the 15th century, it was a small coat worn under a larger one; later, it referred to a woman’s underskirt

Answer: Petticoat

$400 Double Jeopardy! Round questions

26. Category: The 5th Century

Clue: Missionary work by Bishop Palladius & this saint succeeded in converting Ireland to Christianity

Answer: St. Patrick

27. Category: Latin America

Clue: In 1956, this Cuban organized the 26th of July Movement, named for the date of his 1953 revolt against Batista

Answer: Castro

28. Category: The Bible

Clue: In Mark 1, he says, “There cometh one mightier than I after me.”

Answer: John the Baptist

29. Category: City of the Day: New York

Clue: When N.Y.C. was a Dutch settlement, this street got its name because it was a wide thoroughfare for wagons

Answer: Broadway

30. Category: The Library

Hint: The word “library” comes from the Latin “liber,” which means this

Answer: Book

$800 Double Jeopardy! Round questions

31. Category: Orphans in Books

Clue: This Beverly Cleary girl has a mom & dad; Helen Hunt Jackson’s 1884 character of the same name does not

Answer: Ramona

32. Category: Four-Letter Opposites

Clue: Copious: a way to serve meat

Answer: Rare

33. Category: Outlaws

Clue: Sam Bass was a Texas cowboy who stole from the rich & gave to the poor until captured by these lawmen

Answer: The Texas Rangers

34. Category: “S” Tough

Clue: Gee, ghee is a big export from this country, whose capital is Mogadishu

Answer: Somalia

35. Category: Chemistry

Clue: Putting a little sodium into a Bunsen burner flame will turn the flame this color

Answer: Yellow

$1,200 Double Jeopardy! Round questions

36. Category: Psychology

Clue: Term for what occurs when a 6-year-old boy fights for the attention given his little sister

Answer: Sibling rivalry

37. Category: The French Revolution

Clue: A coup on 18 Brumaire established the consulate & brought this general to power

Answer: Napoleon Bonaparte

38. Category: Classical Literature

Clue: A coup on 18 Brumaire established the consulate & brought this general to power

Answer: Metamorphoses

39. Category: U.S. Presidents

Clue: When elected president in 1856, he had just served three years as minister to Great Britain

Answer: James Buchanan

40. Category: Movie Stars Old and New

Clue: In 1932, David Manners was the hero of “The Mummy”; in 1999, it was this actor

Answer: Brendan Fraser

$1,600 Double Jeopardy! Round questions

41. Category: State Flora

Clue: Hawaii’s state plant is kalo, the local name for this root used to make poi

Answer: Taro

42. Category: Nicknames

Clue: Alexis I, the second czar of this dynasty, reigned 1645-1676

Answer: The Romanovs

43. Category: Daniel Radcliffe

Clue: It wasn’t just another day at the office for Daniel when he guested on “Extras”, starring this British comic as Andy

Answer: Ricky Gervais

44. Category: Dining Out

Clue: A dish served “Veronique” is garnished with this fruit

Answer: Grapes

45. Category: Mountains

Clue: Some of the finest singing canaries are bred in the Harz Mountains of this country

Answer: Germany

46. Category: Beastly Novels by Character

Clue: Fly, Rex, Farmer Hoggett

Answer: Babe

$2,000 Double Jeopardy! Round questions

47. Category: Big Ben

Clue: In 1598, this dramatist killed an actor in a duel, no doubt putting him out of his humor

Answer: Ben Jonson

48. Category: T.V. Monsters

Clue: There were also vampires & werewolves on this Showtime series, with characters like Dorian Gray & Victor Frankenstein

Answer: Penny Dreadful

49. Category: An Atomic Category

Clue: These subatomic particles come in 6 flavors, including up, down & strange

Answer: Quarks

50. Category: Famous Names

Clue: Familial relationship of Madame Sun Yat-sen to Madame Chiang Kai-shek

Answer: Sisters

Final Jeopardy! Round questions

51. Category: Colleges and Universities

Clue: The College of Engineering at the University of Nevada, Las Vegas is named for him

Answer: Howard Hughes

52. Category: Medical History

Clue: One of the first recorded autopsies was performed on this man & revealed 23 puncture marks

Answer: Julius Caesar

53. Category: Famous Americans

Clue: In 1936, at age 79, he published an article in Esquire magazine in which he described how to pick a jury

Answer: Clarence Darrow

54. Category: U.S.A.

Clue: This community outside Washington, D.C., is named after a Presbyterian church built there in 1820

Answer: Bethesda, Maryland

55. Category: U.S. Presidents

Clue: The last Democratic president before 1985 to serve two complete terms, no more, no less

Answer: Woodrow Wilson

56. Category: Business & Industry

Clue: Salvaged from a shipwreck in the 1850s, the Lutine Bell hangs in its British headquarters.

Answer: Lloyd’s of London

57. Category: Political Quotations

Clue: It was said that being with these two leaders, born in 1874 & 1882, “was like sitting between 2 lions roaring at the same time.”

Answer: Winston Churchill and Franklin Delano Roosevelt

58. Category: Contemporary American Authors

Clue: This Pulitzer winner changed his first name to that of an Irish king, avoiding associations with a famous ventriloquist’s dummy

Answer: Cormac McCarthy

59. Category: U.S. State Names

Clue: The two states whose 1-word names are contained in other state names

Answer: Kansas (Arkansas) and Virginia (West Virginia)

60. Category: Brands

Clue: Babe Didrikson Zaharias, Evan Strong & Roy Campanella broke barriers representing this brand

Answer: Wheaties

Strategies for Playing and Winning Jeopardy!

Congrats! You have now tested your knowledge. How’d you do?

If you’ve ever thought about auditioning for Jeopardy! or even just playing for fun with friends, you might benefit from taking a step back and contemplating your game strategy.

Here are a few strategies you could consider employing.

Familiarize yourself with common categories.

It’s impossible to study every category since Jeopardy! Comes up with new ones every episode. But, there are a few reliable categories that are worth studying.

As Brad Rutter, a Jeopardy! Great, who has won the most money on Jeopardy! of all time, says in this interview^{1https://www.denofgeek.com/tv/jeopardy-brad-rutter-the-chase-alex-trebek/}, “They can conceivably ask you about anything, but you know that presidents are going to come up a lot, Shakespeare is going to come up a lot, world capitals are going to come up a lot. So I generally try to stay in shape with that type of stuff.”

Watching Jeopardy! with friends can be a fun social experience. If you’d like to build some further skills to make your social experiences even more enjoyable, you could check out this free goodie:

Strengthen your weaknesses

It might be a good idea to write out the categories you know you excel in and the ones that are harder for you and then give yourself time to read about the latter.

Superchamp Matt Amodio^{2https://www.vulture.com/article/jeopardy-champion-matt-amodio-interview-winning-streak-strategy.html} says in an interview that he knew he was strong in categories like history and geography but weaker in pop culture. So he went on T.M.Z. to read about celebrities and let his curiosity take him into internet rabbit holes, learning about the ins and outs of celebrity culture.

Take practice tests

You can either watch re-run episodes or take this official Jeopardy! Practice test, or go through the archive of Jeopardy! Episodes.

However, you choose to approach it. Keep reading, consuming media, and taking practice tests.

Bet big on Daily Doubles.

James Holzhauer (who won the most money on a single episode in Jeopardy! history) changed Jeopardy! Strategy forever when he brought in his sports-betting background.

Holzhauer’s main strategy^{3https://www.theatlantic.com/entertainment/archive/2019/04/james-holzhauer-jeopardy-1-million-win-or-lose/587878/} for winning so much money was to go all in on Daily Doubles.

He recognized that he would get the Daily Double questions correct far more often than not. So, statistically, the best strategy is to bet everything on those questions every time. Sometimes, you’ll lose it all, but statistically, you’ll gain far more than you’ll lose.

Develop effective wagering techniques.

There is a general algorithm^{4https://thejeopardyfan.com/final-jeopardy-betting#:~:text=General%20Wagering%20Strategy%20Algorithm&text=Determine%20the%20leader’s%20optimum%20cover,cover%20bet%20from%20their%20score).} for how much to wager in the Final Jeopardy! Round depends on how much money each contestant has and your confidence in your answer.

Let’s go over the algorithm with an example game: 

Say the Leader has $20,000, the Second player has $14,000, and the Third player has $2,000.

How much the Leader should bet if they are confident in their answer

To find the Leader’s optimal bet against the Second player, you’d double the score of the Second player, add a dollar, and then subtract the Leader’s current score. So, the calculation is: (14,000 * 2 = 28,000; 28,001 – 20,000 = 8,001). This $8,001 is the amount the Leader should bet. If they both get the question right, the Leader maintains their first-place lead. 

How much the Leader should bet if they are confident in their answer

If the Leader is not confident in their answer, they might just consider betting nothing and hope the Second player doesn’t surpass them.

How much the Second player should bet if they are confident in their answer

If they are confident, the Second player should go all in to try to surpass the leader.

How much the Second player should bet if they are unconfident in their answer

Now, let’s imagine the Leader made the bet and lost. Their score would then be their current score minus the calculated bet: 20,000 – 8,001 = 11,999. Both the Second and Third players should aim to ensure their score gets (or stays) above this number to overtake the Leader. Unfortunately, in this case, the Third player is out of the running, as doubling their score still wouldn’t be enough (2,000 * 2 = 4,000), which is less than the Leader’s score if the Leader loses their bet. 

If the Second player is unconfident in their answer, they could consider only betting 2,000. This way, if the Leader did bet 8,001 and lost, it’d bring their score down to 11,999. So if the Second player only bets 2,000 and loses, their score would drop to 12,000, and they’d win.

While the Second-place player wants to steal the top spot, they must also consider that they mustn’t slip into third. So they ought to repeat the same process: double the Third player’s score, add one dollar, and subtract it from the Second player’s current score: (2,000 * 2 = 4,000; 14,000 – 4,001 = 9,999). If the second player wants to be more cautious, they should limit their bet to 9,999 so that they don’t slip into Third place.

How much the Third player should bet

The Third player should base their bet on what the scores of the Leader and Second player would be if they both answered incorrectly. They need to predict how much they’d need to win in order to surpass both of these adjusted scores. 

Here’s a wild video of what can happen if you don’t bet properly!

Iconic Moments from Jeopardy!

Jeopardy! has been on the air for over thirty-five years. Over that time, it has given us some of the most iconic moments and memorable episodes in television history. 

Here are a few to remember.

A.I. beats the best

In 2011, I.B.M.’s A.I. model Watson competed against the two best Jeopardy! Players Ken Jennings and Brad Rutter. In an intense match, Watson ended up winning.

Given that we now have Google and ChatGPT, it may seem obvious that an A.I. could gather data faster than a human. But at the time, this was groundbreaking and set the stage for what was possible. 

Another exciting A.I. frontier is reading body language. If you’re curious about the topic, here’s an informative article.

If you’d like to watch a 10-minute documentary on the event, you can check that out below:

Alex Trebek’s cancer announcement

In 2019, Alex Trebek announced to the Jeopardy! Fanbase that he had pancreatic cancer.

While he delivered the news with optimism and levity, it was a heavy moment, and fans continued to support him for his next few years of life.

Here is a video of his announcement:

Trebek’s tribute

After Trebek passed, Jeopardy! Aired the final episode with him as the host. The episode included a tribute to his career in a short and sweet video. 

Other iconic moments

Over the years, Jeopardy! Footage accumulated plenty of quirky and humorous moments. Here’s a YouTube montage that highlights some of the more memorable ones.

Famous Jeopardy! Lore and Trivia

History of Jeopardy!

Merv Griffin created the original Jeopardy! In 1964. The modern version was re-launched in 1984 and is taped at Sony Pictures Studios in Culver City, California. It is the same studio where shows like Wheel of Fortune, The Price Is Right, and The Young and the Restless are filmed. 

They film five episodes of Jeopardy! a day, twice a week. 

Alex Trebek hosted nearly 8,000 episodes from 1984 until his passing in 2020. Upon his death, Trebek had his entire wardrobe (including 300 neckties^{5https://www.nytimes.com/2021/02/18/us/alex-trebek-wardrobe-doe-fund.html#:~:text=When%20he%20died%20in%20November,a%20day%2C%20twice%20a%20week.}!) donated to homeless men and men who had just gotten out of jail.

Theme song

Merv Griffin, who created both Jeopardy! and Wheel of Fortune, also wrote the iconic theme song from Jeopardy! It only took him 30 seconds to write the song, originally a lullaby for his son, which he called “A Time for Tony.” When he used the song for Jeopardy!, he renamed it “Think.” 

Griffin would receive royalties every time the song played. Those royalties have stacked up to nearly $100,000,000 (including the years since his death in 2007).

Where the premise for the show came from

While on a flight in 1963, Merv Griffin and his wife Julann devised a unique twist for a game show concept^{6https://www.smithsonianmag.com/arts-culture/How-Merv-Griffin-Came-Up-With-That-Weird-Question-Answer-Format-for-Jeopardy-180949815/} in response to quiz show scandals of the 1950s. Julann suggested reversing the game dynamics by providing answers and having contestants come up with the questions.

At first, Merv didn’t understand. Until Julann said, “The answer is ‘5,280.’”

To which he responded, “The question is, ‘How many feet in a mile?’”

She went on, “The answer is ‘79 Wistful Vista.’”

And Merv came back with “‘Where did Fibber McGee and Molly live?’”

They kept going back and forth, and by the time the plane landed, the premise for Jeopardy! was born.

Longest win streak

Ken Jennings (now the host) won a historic 74 games^{7https://www.jeopardy.com/contestant-zone/leaderboard-of-legends} in a row in 2004.

Second place is Amy Schneider, with 40 games in 2022.

And third place is Matt Amodio, with 38 games in 2021.

Seven of the top ten win streaks occurred since 2019.

Most money won

James Holzhauer won the most money^{7https://www.jeopardy.com/contestant-zone/leaderboard-of-legends} in a single game of Jeopardy! with $131,127 in 2021. Interestingly, Holzhauer also holds the record for the second through tenth place for most earnings in a game. One main reason Holzhauer won such a large amount of money is because he had a history in sports betting.

Brad Rutter has won more money than any other Jeopardy! Player overall with total earnings of nearly 5 million dollars.

How to create your own Jeopardy! style questions

Creating your own Jeopardy! Style questions can be a great way to test your knowledge, challenge friends and family, or even just have fun. To craft quality questions for your own game of Jeopardy! Here are seven tips on how to get started.

• Brainstorm topics. Think about what you know well or what interests you—and then try to come up with questions about those subjects. 
• The appropriate level of difficulty. Determine how difficult you’d like to make your game of Jeopardy! How trivia savvy is the audience? Is the purpose of your game stiff competition or lighthearted fun? 
• Think of clues. A good clue should be specific enough that there is only one right answer but vague enough that it has multiple layers of understanding.
• Research reliable sources. When forming your questions, ensure you use sources that are reliable and up-to-date; if possible, double-check facts by consulting multiple sources. Don’t rely on Wikipedia or ChatGPT. Make sure you double-check references against primary source documents whenever possible. 
• Mix up clue formats. Instead of writing standard open-ended questions, consider using other formats such as multiple choice or fill-in-the-blank answers for added complexity or variety. 
• Incorporate visual elements. Including visuals can also add another layer of interest; photos or videos can serve as clues and create visual interest while adding context and clarity for both readers and players alike.
• Make sure there’s only one correct answer. Remember, each question has only one correct answer. If it’s a multiple-choice question, you can include two wrong answers (or more) that sound plausible but are not actually correct (these are called distractors). 

With these tips and strategies, you should now have all the knowledge necessary to create your own Jeopardy! Game show! Have fun with it 🙂

Suppose you’d like to create a non-Jeopardy! For trivia night, you might enjoy this list of apps and third parties to help with the ultimate trivia party.

Frequently Asked Questions About Jeopardy! Questions and Clues

Takeaways on Jeopardy! Questions

Hopefully, you enjoyed some of the practice questions above!

If you’d like to continue to upgrade your Jeopardy! Skills, remember the following tips:

• Familiarize yourself with the categories. Which do you see most often? Presidents, Shakespeare, and world capitals are three categories to brush up on.
• Strengthen your weaknesses. Determine where you have holes in your knowledge base, and then let yourself curiously learn about those topics.
• Take practice tests. One of the best ways to improve is to practice, practice, practice! Check out the archive of Jeopardy! Episodes.
• Bet big on daily doubles. Odds are you’ll get these right more than you’ll get them wrong, so play the stats and bet big.
• Learn wagering techniques. One way to win big is to learn how to bet. Study the algorithm provided earlier in the article.

And if you choose to set up your own Jeopardy game amongst your friends, just remember these tips:

• Determine the desired level of difficulty 
• Make sure you do your research with reliable sources
• Mix up clue formats
• Incorporate visual elements
• Make sure there’s only one correct answer.

There you have it! Good luck on your trivia journey ahead.If you’d like more trivia ideas for a different style of game, you could check out this guide on 150 Family Feud-style questions.