10 of Alex Trebek's Best 'Jeopardy!' Moments

Jeopardy Alex Trebek
Sony Pictures Television / Courtesy: Everett Collection; Jeopardy Inc; ABC/Eric McCandless

With charm, wit and warmth, Alex Trebek reigned over the blockbuster game show Jeopardy! for 36 years. While he may be gone, the host's best moments live on, from great April Fool's pranks and the beginning of Celebrity Jeopardy! to some heartwarming contestant interactions.

Below, relive 10 of Trebek's best moments throughout the years.

'More Goofy Uncle Than Stern Dad': 5 Reasons Why We'll Miss Alex Trebek on 'Jeopardy!' (VIDEO)See Also

'More Goofy Uncle Than Stern Dad': 5 Reasons Why We'll Miss Alex Trebek on 'Jeopardy!' (VIDEO)

From his poise and intellect to his good-natured sarcasm, the top reasons we loved the game show host.
Courtesy of Jeopardy Productions Inc

1984: Alex's Inaugural Episode

After hosting 11 previous game shows, on September 10, 1984, Trebek stepped onto the set he would command into the next century. “In the nearly 50 years since I arrived in the United States,” the Canadian told ABC News in 2019, “I’ve been gainfully employed for all of that time except maybe six months.… That’s a pretty good record.”

BOB RIHA JR./GETTY IMAGES

1992: First Celebrity Jeopardy!

The inspiration for Saturday Night Live‘s long-running spoof began when Trebek welcomed Carol Burnett, Knots Landing‘s Donna Mills and Regis Philbin for the star-studded charity tournament. Future players would include Jodie Foster, David Duchovny and Stephen King. During 2009’s Celebrity tournament, CNN’s Wolf Blitzer played so poorly against Andy Richter and Dana Delany that he found himself $4,600 in the red. Trebek slipped him some pity cash so he had something to bet with in Final Jeopardy! 

Courtesy of Wheel of Fortune

1997: Wheel of Jeopardy!

Heads were spinning on April Fools’ Day when Trebek swapped jobs with Wheel of Fortune host Pat Sajak, who took the Jeopardy! helm but also competed on his own show alongside letter-turning costar Vanna White. (The pair solved the bonus round puzzle together for charity.) 

Courtesy of Jeopardy Productions Inc.

2001: The Mustache Is Going

Trebek admitted on a Canadian talk show in 2008 that he decided to shave his famous facial hair on “a whim” in between show tapings. He never imagined the uproar it would cause: “The mustache got play in newspapers and television all over the country!”

Sony Pictures Television / Courtesy: Everett Collection

2004: Ken Jennings Dominates

Fans were captivated by the software engineer’s 74-win reign, which ended when real estate agent Nancy Zerg — whom Trebek called “a giant killer” — bested him in Final Jeopardy! (He won a record total $2.5 million.) “All good things have to come to an end,” Trebek noted as the rarely seen audience was shown giving both players a standing ovation. Jennings joined the staff of Jeopardy! this season as a consulting producer and will appear in video categories within episodes. 

Courtesy of Jeopardy Productions Inc

2005: Who Needs Pants?

Trebek dropped trou — and cracked up fans — during Season 21’s Ultimate Tournament of Champions after overhearing brainiacs Jennings, Brad Rutter and Jerome Vered backstage. The men talked about easing the tension by taking the stage sans slacks, but it turned out they were only joking. 

Courtesy of Jeopardy Productions Inc

2007: A Three-Way Tie!

Even Trebek was shocked during Final Jeopardy! after all three players (from left: Scott Weiss, Jamey Kirby and Anders Martinson) earned a return visit by correctly answering with wagers that netted them each $16,000. “Aha!” he shouted happily. “For the first time ever, a three-way tie!” Nine years later, a match would end with a trio of contestants all zeroing out with incorrect answers, meaning that none of them would return the next day.  

Buzzy Cohen Jeopardy
Courtesy of Jeopardy Inc

2016: Good-Natured Ribbing

Los Angles music exec Buzzy Cohen shared cheeky exchanges with the fun-loving host during his nine-game run, which saw him write answers like, “What is See You Tomorrow, Trebek?” The day after Trebek’s passing, Cohen — who also won 2017’s Tournament of Champions and served as a team captain for 2019’s 35th anniversary Jeopardy! All-Star Games — said that “Alex’s genius was really that he made the contestants the center of the show.… You really felt when you were on the stage or watching that he was rooting for [them].”

Dhruv Gaur Jeopardy
Courtesy of Jeopardy Inc

2019: We Love You, Alex!

There wasn’t a dry eye in any of our houses when Dhruv Gaur used his Final Jeopardy! response to send some love to a clearly emotional Trebek, who had just announced that he was again undergoing chemotherapy for his cancer. It was, without question, the best answer we’ve ever seen.

James Holzhauer Jeopardy
Courtesy of Jeopardy Productions Inc.

2019: James Holzhauer Falls Short

The pro gambler was set to surpass Jennings’ total winnings after already breaking the show’s single-night record with $131,127, but his 32-game streak came to an end when he was outwagered by librarian Emma Boettcher. He still walked away with $2.46 million.

Jeopardy GOAT Tournament
ABC/Eric McCandless

2020: The Greatest of All Time

“[What] I enjoy most about the show is the 30 minutes I spend onstage with the contestants,” Trebek told TV critics in 2019 of this four-night showdown between top-winning champs (from left: Holzhauer, Jennings and Rutter). “And with these three, it was particularly enjoyable. I hate spending time with stupid people.”