The Hardest 'Jeopardy!' Questions of All Time

Adrienne Westenfeld
·4 min read
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Even the greatest Jeopardy! players of all time get it wrong sometimes. After all, the game wouldn’t be any fun if it was too easy, right? But if you’re wondering just how fantastically Jeopardy! players have gotten it wrong, you’ve come to the right place.

Below, we’ve rounded up 20 Jeopardy questions that fall in a rare and ignominious category called “triple stumpers”—a.k.a., legendarily hard questions. A triple stumper is a clue for which no correct response is given by any player. That can mean a few things: either some or all of the players buzz in incorrectly, or no one buzzes in at all.

Some of these questions are hard as hell, touching on arcane corners of the trivia world (opera categories, for example, are always an albatross around contestants’ necks). Others seem way too easy to be triple stumpers, and expose just how little some Jeopardy! contestants know about slang or sports. In 2018, one category titled “Talkin’ Football” contained five triple stumpers, astonishing the studio audience, viewers at home, and Alex Trebek himself. “If you guys ring in and get this one, I will die,” Trebek joked when the final clue rolled around, following four triple stumpers.

Related video: A look back at Alex Trebek's incredible career

Test your mettle on these triple stumpers, and see if you’ve got what it takes to outsmart some of the most brilliant people on the trivia scene. If you do, maybe it’s time you audition for Jeopardy! and make your own mark on the beloved quiz show’s history.

Category: Places

Question: At the heart of a major industrial region, this 2nd-most populous U.K. city lies near the geographic center of England.

Answer: What is Birmingham?

Category: Opera Zingers

Question: “You inconsiderate jade” is one of the nicer things said to Polly in this 1728 “opera” that inspired the 20th Century “Threepenny Opera.”

Answer: What is “The Beggar’s Opera”?

Category: Jump Around!

Question: You “gotta” do this slang term to mean you’re leaving; it’s also good to get one in the polls.

Answer: What is bounce?

Category: The Middle Ages

Question: One way to judge guilt was “trial by” this six-letter word, like putting the accused’s arm in boiling water.

Answer: What is ordeal?

Category: Potpourri

Question: If you know the correct procedure, you “know” this, also a tool.

Answer: What is the drill?

Category: Broadway lyrics

Question: In a song from Chicago, we’re told to “give ‘em the old” this title, “give ‘em an act with lots of flash in it.”

Answer: What is razzle dazzle?

Category: TV Title Pairs

Question: Paul Michael Glaser & David Soul

Answer: Who are Starsky & Hutch?

Category: Van Gogh A-Go-Go

Question: One theory about Van Gogh’s odd behavior is poisoning from this liqueur made from wormwood.

Answer: What is absinthe?

Category: Who Wrote It?

Question: “We asked you to speak about women and fiction—what has that got to do with a room of one’s own?”

Answer: Who is Virginia Woolf?

Category: Scrambled Harry Potter Characters

Question: A rival & nemesis: MY ALOOF CARD

Answer: Who is Draco Malfoy?

Category: Sports Nobility

Question: This controversial head coach led Indiana to 3 NCAA hoops titles & the U.S. to a gold medal in 1984.

Answer: Who is Bobby Knight?

Category: From the Greek

Question: The science of determining a tree’s age by looking at its growth rings.

Answer: What is dendrochronology?

Category: The Not So Vicious Circle

Question: 1989 film in which Keanu Reeves tells Alex Winter, “Strange things are afoot at the Circle K.”

Answer: What is Bill & Ted’s Excellent Adventure?

Category: Sci-Pourri

Question: The 3 most basic types of clouds are stratus, cumulus, and this high, wispy type with a name meaning “curl.”

Answer: What is cirrus?

Category: Time to Jazz-ercise

Question: This singer was homeless for the year before her big break, winning an amateur contest at The Apollo Theater in 1934.

Answer: Who is Ella Fitzgerald?

Category: World History

Question: This castle famous for its “stone” was built by Cormac MacCarthy about 1446.

Answer: What is the Blarney?

Category: Royalty

Question: Machiavelli was a big fan of this king of Aragon born in 1452.

Answer: Who is Ferdinand?

Category: Talkin’ Sports

Question: Your choice: do or don’t name this play in which the QB runs the ball & can choose to pitch it to another back.

Answer: What is option play?


Category: Canadian Cities

Question: In 1992, this city’s velodrome, once used in the Olympic Games, was transformed into an environmental biodome.

Answer: What is Montreal?

Category: We’re in Business

Question: American Airlines offers this, the oldest frequent flyer program.

Answer: What is AAdvantage?

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