Alex Trebek Made Jeopardy! A Joy To Watch – And Here Are 40 Of His Most Memorable Moments

Alex Trebek was an iconic figure of American television. A whole generation grew up hearing his warm, witty comments as he presented the game show Jeopardy!, and they heard firsthand about his battle with pancreatic cancer. Sadly, the disease claimed him after a two-year fight. But his legacy lives on in the hilarious or heartwarming moments he shared.

40. Trebek helps with a proposal

What could be more romantic than proposing to your lover on Jeopardy! Well… maybe a few things, but it’s what one couple wanted and Trebek helped make it perfect for them. Michael Pascuzzi asked Maria Shafer for her hand, and she answered yes straight away. Trebek joked, “Maria, you responded too quickly. I was about to say we’ll have the answer to that question right after this commercial break.”

39. “What is you doing baby?”

Back in October 2018 Jeopardy! contestant Erik Agard found he couldn’t answer a question, so he turned to the world of online memes and wrote down “What is you doing baby?” instead. Trebek was completely baffled, saying simply, “Well, I’m responding incorrectly.” But the moment went down in both internet and meme-lover history, as it should.

38. Trebek brings his kids onto the show

Trebek was the father of three children. And back when two of them, Emily and Matthew, were still young he decided to bring them onto Jeopardy! The host told the audience, “The kids had no school today, so I promised six-year-old Emily and nine-year-old Matthew that they could attend a taping of our show.” Now that’s gotta be the best bring-your-child-to-work day ever.

37. A memorable answer

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In 2013 Trebek asked teenage contestant Leonard Cooper who said, “The eyes of the world are upon you.” The correct answer was Dwight D. Eisenhower, but Cooper wrote down, “Who is some guy in Normandy. But I just won $75,000!” Trebek delightedly responded with, “You did indeed, way to go!”

36. A cameo on The Simpsons

Of course anyone who’s anyone has appeared on The Simpsons and Alex Trebek is no exception. He popped up in the episode “Miracle of Evergreen Terrace” where Marge goes on Jeopardy! to try and win $15,000 for Springfield. Although, this particular version of Trebek treats failed contestants rather differently.

35. Trebek pays tribute to a contestant

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In December 2016 an episode of Jeopardy! ended with a very special tribute. A six-day champion of the show, Cindy Stowell, had died of metastatic colorectal cancer before her episodes had even made it to air. Her winnings had been donated to research for a cure. Trebek celebrated her life on the show — this has an even sadder resonance now after his own death from cancer.

34. Trebek goes minus his pants

Trebek believed in keeping his contestants amused and comfortable, even if that meant occasionally doing embarrassing things. During the 2005 Tournament of Champions, he decided to ease all the tension by walking out on the Jeopardy! stage without his pants on. And of course, the television cameras captured the moment forever.

33. A contestant gives a silly answer

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If you don’t know the answer to a question, sometimes it’s best to take a guess. That’s what one Jeopardy! contestant did back in 2014 when Trebek asked her what “Selenophobia” was. She answered, “What is fear of Mexican music stars?” a reference Queen of Tejano music Selena Quintanilla and — hopefully! — a joke. Trebek laughed and said no, but he thought the response was great.

32. Trebek makes his cancer announcement

Trebek’s way of dealing with his cancer diagnosis was truly impressive. When he made the announcement in 2019 not only did he do it informatively and calmly, he even made a joke. He told his fans, “I plan to beat the low survival rate statistics for this disease. Truth told, I have to! Because under the terms of my contract, I have to host Jeopardy! for three more years!”

31. Trebek finds himself at the wrong end of a joke

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Remember when the meme “Okay Boomer” was a thing? It even popped up on the showIn January 2020 Trebek asked famed Jeopardy! contestant Ken Jennings, “A 2019 New York Times article says this two-word phrase ‘marks the end of friendly generational relations.’” A delighted Jennings called, “I get to say it to Alex! What is ‘Okay, Boomer?’” Luckily Trebek took it all in good humor.

30. Kareem Abdul Jabbar accidentally reveals too much

In 2012 NBA icon Kareem Abdul Jabbar, who Trebek’s always been a fan of, appeared on Jeopardy! Trebek put an innocuous question to him, namely “The five movie ratings in the US are NC-17, R, PG, PG-13 and this one.” The basketball star suggested, “X?” The correct answer is G (NC-17 replaced the X-rating in 1990). Well, they do say never meet your heroes.

29. Trebek calls a contestant weird

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Some great Muppet-related banter happened on Jeopardy! in March 2018. Champ Lisa Mueller told a story about a letter she once wrote to Big Bird, telling him, “My third favorite color is yellow, just like you are.” At this, Trebek remarked, “You get the feeling that our current champion is a little weird?” When Mueller looked a little shocked at this, Trebek added, “You disrespected Big Bird. You’re lucky to be here.”

28. Trebek starts campaigning

In October 2019 Trebek partnered up with the World Pancreatic Cancer Coalition to release a PSA about symptoms of the disease. He talked about the risk factors and about what he’d experienced, and asked viewers to join him in the fight against the cancer which was to sadly take his life the following year.

27. Trebek on the X-Files

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One of Trebek’s oddest ever appearances was on supernatural show The X-Files opposite David Duchovny’s Fox Mulder. He played himself… or possibly a Man in Black who just happened to look incredibly like himself. Either way, it made for one of the funniest, weirdest episodes of the hit show’s third season.

26. Trebek wishes his mom a happy birthday

Fans of Trebek and Jeopardy! got a wholesome surprise in 2016 when the host opened an episode by saying he’d like to wish someone a happy birthday. That someone turned out to be his mother, Lucille, who had just turned 95 years old. Trebek was overcome while talking about her and even cried a little. Aww!

25. Trebek wins a Guinness World Record

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Among Trebek’s many achievements is a Guinness World Record. He got the award in 2014, during his 6,829th episode, for “most game shows hosted by the same presenter.” Now that’s impressive, but what’s even more impressive is that he’d never missed an episode. Well, apart from one April Fool’s Day where he traded places with Pat Sajak, but that was all in the name of comedy.

24. Trebek on SNL

Saturday Night Live always did a bit where Will Ferrell played Alex Trebek on a Jeopardy! spoof. And the real Trebek didn’t take offence, the exact opposite in fact, he loved it. He even showed up as part of a “Celebrity Rock ‘n Roll Jeopardy!” sketch in 2002, since it was Ferrell’s last show as a cast member.

23. The “We love you Alex” moment

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While Trebek was fighting cancer in November 2019, a contestant decided to give him some encouragement. Dhruv Gaur wrote, “We love you, Alex,” as one of his answers and sure, he failed the question, but he won the hearts of viewers everywhere. Trebek himself was so touched by the moment he was close to tears.

22. A contestant brags

During a 2014 Jeopardy! show, contestant Ari Voukydis couldn’t think of the answer, so he threw caution to the wind and wrote down, “Who is this handsome gentleman” with an arrow pointing at himself. He didn’t win of course, but his efforts won him a “good for you!” from Trebek which might have been an even better reward.

21. Trebek is insensitive about a goat

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Alas, Trebek once started giggling at what was totally the wrong time. A contestant called Laura revealed she once had a pet pygmy goat who ate everything, including a bag of Quikrete which killed it. A laughing Trebek asked “Was it a 60-pound or 80-pound bag?” and got an “Alex, you’re being insensitive!” from Laura. He agreed with her, but the laughter continued.

20. Trebek praises Kobe Bryant

Trebek always loved the Los Angeles Lakers, and when Kobe Bryant played his last game in 2016 the game show host filmed a special clip for him. Trebek said, “Kobe will have a great post-basketball playing career.” But since both men passed away in 2020, the clip now just seems heart-wrenchingly poignant.

19. A contestant wins with the smallest amount

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It was back in 1993 when a contestant set a record for winning Jeopardy! with the smallest possible amount, one single dollar. This was Air Force Lieutenant Colonel Darryl Scott, and Trebek was blown away. He shouted, “Lowest total ever! But congratulations!” The same thing wouldn’t happen again until 2017.

18. Trebek roasts a contestant

In 2016 a contestant called Susan Cole tried to sell Trebek on a musical genre called “nerdcore.” According to her it was, “people who identify as nerdy rapping about the things they love: video games, science fiction, having a hard time meeting romantic partners…” Trebek quipped, “Losers, in other words.” Ouch!

17. “Let’s Rap, Kids!”

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Perhaps surprisingly, Trebek was pretty into hip-hop. Every so often on Jeopardy! he’d rap, and it was amazing. During a 2017 episode with a category called “Let’s Rap, Kids!” he took it upon himself to cover Kanye West, Drake, Lil Wayne and more. He said he hoped he wouldn’t be hearing from West afterwards, but who knows, the rapper might have liked it. Everyone else did.

16. A contestant pays tribute

In one January 2020 episode, a contestant named James Holzhauer wrote out a tribute to Trebek as one of his answers. He wrote “Who is the GHOST? (Greatest Host of Syndicated TV) Alex Trebek.” But he’d had some fun with it as he’d written Pat Sajak’s name first and then crossed it out. It was both touching and completely hilarious.

15. Trebek appears on Conan

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Conan O’Brien had a bit on his show called “Alex Trebek Has Gone Insane” where he randomly edited together bits of Trebek footage with hysterical results. But in 2014 it seemed Trebek wasn’t taking it lying down anymore. He popped up on the show and this time he had an edited video… of Conan.

14. Someone forgets Trebek’s name

How could you possibly get Alex Trebek’s name wrong? But one Jeopardy! announcer managed it by introducing the host as “Glenn Trebek.” Even so, the host was totally cool about it, telling the audience his stand-in was named Glenn, so that was the source of the confusion. He added that his announcer had “made a mistake for the first time in 16 years.”

13. Trebek jokes about how he got the job

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In 2017 the website Business Insider spent a whole day interviewing Trebek behind the scenes of his show. At one point journalist Graham Flanagan asked him how he’d gotten the Jeopardy! job. Trebek answered, “They phoned me one day and said, ‘We’re bringing Jeopardy back on the air, we’d like you to host it.’ I said, ‘Will you pay me?’, they said ‘Yes,’ I said, ’Okay, I’m your man.’”

12. Trebek calls a contestant a groupie

During the 2010 College Championship Trebek met a contestant who wanted to be a rock journalist, leading Trebek to jokingly label her a “groupie.” This was a rare example of a Trebek joke completely failing to land, and he caught some heat from it. The woman in question confirmed in a post that she did greatly enjoy her time on the show, though.

11.  A contestant writes Trebek’s name backwards

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Trebek once appeared on the cartoon Family Guy, voicing a parody of himself. That animated Alex Trebek could be banished to the Fifth Dimension by writing his name backwards… so of course, one contestant just had to try this on Jeopardy! Trebek pretended not to understand the joke and remained in this dimension.

10. A contestant talks about Trebek’s impact

After Trebek passed away pre-taped episodes of Jeopardy! continued to air. One of them was very special indeed, as a contestant called Burt Thakur stopped to tell Trebek how much he meant to him. Brushing away tears, Thakur said he’d learned English because of Trebek. The emotional look on the host’s face said it all.

9. Trebek does some mime

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Trebek developed his own football category for Jeopardy! It involved him miming out referee signals and contestants had to guess what they were. It was all pretty funny, especially since the official Jeopardy! social media posted some pics of Trebek’s carefully drawn signals and questions. The host had super neat handwriting too, but did anyone expect anything else?

8. A contestant might have been in a cult

Trebek got more than he bargained for when he chatted to a contestant in 2012. She was part of “the Order of the Blessed Saint Scully the Enigmatic.” This was “a cyber-abbey devoted to the wisdom of the character of Dana Scully from The X-Files,” apparently. But, she admitted, “some people would call it an internet cult.” Trebek, who had seen it all by this point, simply commented that hey, he’d been on The X-Files once.

7. Trebek talks about his wife

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Trebek’s wife, Jean, was by his side as he fought cancer. In an interview for Good Morning America in July 2020, Trebek teared up as he spoke about her. Jean, he said, “has so much goodness in her that she is always giving out, always putting out to help me get over difficult moments…I’m just in awe of the way she handles it.”

6. “What are THOSE?”

There are plenty of meme references on Jeopardy! In November 2016 a teen called Sabrina couldn’t think of an answer during the show, so she just wrote, “What are THOSE?” a reference to a hugely popular internet meme at the time. Trebek didn’t get it — or maybe just pretended not to. Either way, he said the line and Twitter went nuts.

5. Trebek forgets the name of his own show

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Yep, Trebek was on quiz shows before Jeopardy! came along. Unfortunately, his memory failed him when he had to relay the question, “In July of 1973 this game show, my first in America, debuted on NBC,” on Jeopardy! Not only did the contestants not know it, Trebek didn’t either. He thought it was called “The Wizard of Oz” when actually it was “The Wizard of Odds.” Oops.

4. Trebek raps the Fresh Prince of Bel Air song

Maybe if the game show thing hadn’t worked out, Trebek could have become a rapper instead. In 2015 he gave a clue about The Fresh Prince of Bel Air and did the theme song flawlessly, rapping “I pulled up to the house around seven or eight, and I yelled to the cabbie ‘Yo Homes! Smell ya later!’” to an absolutely delighted audience.

3. No-one knows anything about football

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Sometimes there’s a fail so epic it goes down in Jeopardy! history. This was the case for three unfortunate contestants named Justin, Ryan and Sara back in 2018. They knew nothing about the sport and were left to stand around awkwardly at the questions. Trebek quipped sarcastically, “I can tell you guys are big football fans.”

2. A contestant references SNL

One contestant came on Jeopardy! with a specific goal in mind and oh man, she was going to achieve it. Talia Lavin wrote, “What is the love ballad of Turd Ferguson?” for one of her answers, just so Trebek would finally say the SNL joke name on air. He did! Oh, and Lavin included a message for her mom too. Aww!

1. Trebek’s first ever episode

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Trebek first started presenting Jeopardy! all the way back in 1984. Back then it was fast, frantic, full of interruptions, and Trebek had a mustache. But obviously, that version of the show had enough of a spark to continue on for decades afterwards. Even legends have to start somewhere, after all.

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