Top 10 Jeopardy Fails of All Time

Written by Aiden Douris

We'll take colossal mistakes for $1000, Alex. Welcome to and today we're counting down our picks for the top 10 Jeopardy fails of all time.

For this list, we're looking at the funniest, most awkward, most downright embarrassing fails in Jeopardy history, while excluding intentionally wrong answers. However funny they may be, those aren't technically fails.

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We’ll take colossal mistakes for $1000, Alex. Welcome to and today we’re counting down our picks for the top 10 Jeopardy fails of all time.

For this list, we’re looking at the funniest, most awkward, most downright embarrassing fails in Jeopardy history, while excluding intentionally wrong answers. However funny they may be, those aren’t technically fails.

#10: “What Is a Donkey?”

You know someone on the Jeopardy team had a fun time coming up with this question. Tasked with providing the name of a punch to the back of the neck that is named after an animal, contestant Mike responds with the not safe for work answer, “Donkey”. For those not in the know, a rabbit punch, the correct answer, is a dangerous and illegal boxing move. A donkey punch however, is a sex act that, well... let’s just say that’s a definition you’ll have to look up on Urban Dictionary for yourself. Let’s just hope Mike’s mom wasn’t recording this episode.

#9: “What Is a Threesome?”

Poor Kara. This one seemed like a set-up from the beginning. Instead of asking for the category of “Group countdown for 600,” another contestant, Roger, simply asks for “group six”... see where we’re going with this? Alex then reads this fitting clue, to which Kara answers “What is a threesome?”. You can tell she regrets her answer immediately as she embarrassingly slaps her forehead while Roger sweeps in with the correct answer, “a love triangle”. What makes this one all the more embarrassing is Alex chiming in stating “Kara has obviously had much more experience than I”. Oh, Alex.

#8: Kareem Abdul-Jabbar’s “X-Rated” Answer

Even celebrities can make epic fails. In this episode of Jeopardy’s 2012 “Power Players Week”, six-time NBA champion Kareem Abdul-Jabbar is given the clue, “The 6 movie ratings in the United States are NC-17, R, PG, PG-13 & This One” and answers with “What is X?”. As Trebek points out, he “went in the wrong direction” - the correct answer was actually the most child friendly rating available,” G”. Aside from the fact that the “X-rating” isn’t actually an official movie rating, it’s hard to imagine adult films being the correct answer in a Jeopardy category. How embarrassing…

#7: “What Is Pussy Furry?”

If the biggest mistakes made by contestants can be lumped into one general category, it would be forgetting that Jeopardy is a family show. Sadly, Raya only remembered that fact half-way through her answer, and her stuttering attempt to stop herself from delivering this inappropriate guess only adds to the hilarity. Her answer of “What is Pussy Furry” followed by a quiet “I don’t know” elicits an understandable eruption of laughter from the audience. The correct answer, of course, was “Kitty Galore” - a nod to the 007 series. While we can see what she was going for, “Pussy Furry” isn’t a term we ever expected to hear on Jeopardy.

#6: Wolf Blitzer’s Big First Round Loss
Where do we even begin with this one? When Journalist and CNN host Wolf Blitzer made an appearance on Jeopardy, nobody could have anticipated the disastrous run that would follow. Answering a series of questions incorrectly, Wolf managed to rack up a whopping total of negative $4,600 in the first round alone. That’s enough to make the average contestant cringe, let alone a renowned journalist. What makes it even funnier is that comedian and late-night sidekick Andy Richter left that same round with $39,000. Hey this doesn’t mean the charity of Wolf’s choice owes Jeopardy some money, does it?

#5: “What Are Public Toilets?”

This one was *ahem* a real stinker. In this classic episode of Jeopardy, Alex reads this clue about 4th Century Rome. Gary answers “What are public toilets” instead of the correct answer, “Public libraries”. While we can see where Gary may have been thrown off course with the use of the word “public” it should have been clear the papyrus was being used for books and not as toilet paper. At least he was a good sport about it as he laughs it off afterwards with Trebek stating he likes Gary’s answer for the humor. Even if it was… toilet humor.

#4: “What Is Toronto?????”

Take that Artificial Intelligence! In 2011, Watson, a supercomputer built to answer questions in natural language, was pit against two of Jeopardy’s most successful contestants. Although all performed well, Watson utilized advance wagering tactics and knowledge of previous games to locate both daily doubles and gain a massive lead for final Jeopardy. That’s when this clue was given. With Ken and Brad both answering correctly, it was as shocking as it was hilarious to watch Watson respond with “What Is Toronto?????”, especially given the category was “U.S. Cities”. While it still won the game, it’s reassuring to know the robot uprising isn’t quite ready yet.

#3: “Who Is Magic Johnson?”

“You miss one hundred percent of the shots you don’t take” is a quote by the man whose name Joe should’ve given in response to this question. Accompanied by the sad sounding “Oh No” from Trebek, Joe misses a question that’s rather easy by Jeopardy standards when he offers up Magic Johnson instead of the correct answer Wayne Gretzky. You don’t need to be a sports fanatic to know that Johnson is the basketball star and Gretzky’s the hockey legend. Evidently not realizing the clue read “NHL” and not “NBA”, this is one shot Joe may have not wanted to take.

#2: Terrible Trio Suffer Multiple Triple Stumpers in 1 Game

Sometimes it’s just not your day. Other times... it’s nobody’s day. This infamous game of Jeopardy had numerous triple stumpers. Nobody seemed to be able to get a consistent string of correct answers, and as such, the episode featured many awkward silences. Quite frankly, the smartest play all game came from Frédérique during final Jeopardy, when she gambled $0 despite being in last place while her peers bet nearly everything they had. It was a calculated move which ultimately won her the game, when, once again, all contestants got it wrong. Frédérique might not have had all the answers, but she found the right solution when it mattered most.

Before we unveil our top pick, here are a few Honorable Mentions:
- Mr. Wrong & Mr. Right
- “Who Was Chris Farley?”

#1: All Teen Contestants Finish with $0

It’s an excruciating moment to behold. In this Teen Tournament’s semi-final match, each contestant put everything on the line in Final Jeopardy with the category of “Capital Cities”. We’re given the clue and then forced to watch in horror as each contestant answers “Dublin”, instead of the correct answer “Belfast”. One by one, their scores are each brought back to $0, turning the game into a three-way tie. Adding insult to injury, Alex then awkwardly explains that this is the first time this has occurred in a tournament and that there will be no winner moving on to the finals from this game. Ouch.
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