20 Best Jeopardy Episodes to Rewatch

Colby Taylor, Zoey Orol, and Alain Norman battle it out in this riveting episode of Jeopardy. These 2017 contestants run through Trebek’s categories, bringing the expertise of a foreign service officer, an attorney, and a professor into one tense arena. All charismatic and qualified, these competitors keep viewers on the edge of their seats for each of this episode’s twenty minutes. 

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Herman Wilkins, Joe Velasco, and Sarah Twilley compete on this enthralling episode of Jeopardy, resulting in a $20,000 sweep. The filmmaker, music teacher, and student bring a creative edge to the Jeopardy stage, with their speed keeping this episode interesting – one of the best Jeopardy episodes in recent years. 

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Trish Floyd, Jeff Brown, and Rob Liguori grace the Jeopardy stage, bringing together the interests and expertise of an actuary, a grant writer, and a research editor. Ending with a $58,601 sweep, this episode features one of the most clear-cut wins in recent seasons, making for a satisfying watch. 

Ken Jennings makes his Jeopardy debut in this riveting episode, embarking on his long-running streak against Chad Kaihe and Carrie Youngblood, a construction inspector and administrative assistant, respectively. Jennings owns the stage in this episode, setting the foundation for a winning streak that places him squarely among the Jeopardy greats.

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Appearing for the first time alongside contestants David Franklin and Regina Sutton, Brad Rutter was the captain of his Manheim Township High Quiz Bowl team. When Rutter appeared on the show in 2000 it was when contestants were limited to five appearances, after which they would be “retired” as undefeated. Rutter was one of these champions and later made most of his winnings through championship tournament play over the subsequent years.

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The 2019 Tournament of Champions Quarterfinal kicks off in this episode featuring Gilbert Collins, Anneke Garcia, and Kyle Jones, who are reigning champs from previous tournament rounds. The Tournament of Champions is at its best in this episode, featuring impressive performances from staunch competitors and some of Trebek’s best wit and charm. 

Rock Wayda, Hannah McIntyre, and Erik Agard compete in this engrossing episode of Jeopardy, playing from Agard’s three-episode winning streak. This episode showcases Jeopardy’s strengths with Agard’s winnings totaling $66K at the episode’s start. Add this episode to your best Jeopardy episodes rewatch list ASAP. 

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Tiebreaker rules were first announced in 2016 but weren’t used until 2017 between contestants Laura and Sara, who were both tied for the lead with $6,799. When all three contestants failed to answer Final Jeopardy correctly, instead of splitting the winnings the two women chose sudden death. In these new rules, Trebek will read one more question and whoever answers correctly first will win the game. Laura was able to answer the question correctly and made for a very memorable Jeopardy game.

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Yoshie Hill, Natalie Craig, and Tracy Lee take the stage in this compelling Jeopardy episode hosted by Alex Trebek at his best. With three Californians in fierce competition, this episode features quick moves, impressive scoring, and unforgettable banter. This one is a perfect addition to your rewatch list and stands out as one of Jeopardy’s best episodes. 

Ben Davis, Patrick Pence, and Cathy Sorge battle it out in this gripping episode ending with a one-day total of over $20,000. The law student, GIS coordinator, and archivist compete for daily doubles, category sweeps, and laughs from Trebek in one of Jeopardy’s best and most rewatchable episodes. 

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It may seem a little crazy, but there have been a couple of times where only one contestant can compete in Final Jeopardy. Kevin Walsh was the most recent contestant in 2020, while the last time before that was in 2015 with Kristin Sausville. This happens when the other two players finish regular play with a negative or zero monetary amount. Whichever episode you decide to choose, both are highly entertaining.

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Three-way ties are extremely rare (one in 7,200), so it makes sense that the first would be included in our best Jeopardy episodes list. The contestants for the historic day were Scott Weiss, James Kirby, and Anders Martinson. Each contestant ended with a score of $16,000 after Final Jeopardy, leading to all three returning the next day to finish the tie. This feat has not been repeated since.

This legendary episode brings Ken Jennings’s impressive winning streak to an end, with realtor Nancy Zerg besting a Jeopardy great. His 74-day streak culminated in a total winnings of over $2.5 million, shattering previous records and bringing Ken Jennings into the public consciousness for years to come. 

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Roger Craig, Ken Jennings, and Brad Rutter compete on a star-studded Jeopardy stage in the Battle of the Decades Final. The three compete for Jeopardy notoriety, bringing some of the most well-known names in the show’s history into one room. If you enjoy quick and accurate answers, this is a great episode to rewatch.

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Brad Rutter, a $3.2 million winner of Jeopardy prominence, and Ken Jennings are challenged in this episode by Watson, a question-answering computer by IBM. Because Jennings had never been defeated by a human competitor, Jeopardy decided to challenge him with a computer, leading to a multi-episode IBM Challenge series. 

Bringing the debut of Celebrity Jeopardy, this episode features Regis Philbin, Donna Mills, and Carol Burnett, bringing a new element to the game of Jeopardy. Trebek is on top hosting game in this episode, bringing more entertaining banter and humor than usual with these less-polished contestants. 

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There are dedicated, die-hard Jeopardy fans, and then there is Cindy Stowell. When she recorded her episodes, Stowell was suffering from Stage 4 colon cancer and competed on painkillers while fighting a fever. Her six-game winning streak was witnessed by the world, and she pledged to donate over $100,000 in winnings to the Cancer Research Institute. Even though Stowell passed before seeing her episodes on TV, she made a huge impact on the Jeopardy stage and earns her spot on our best Jeopardy episodes list.

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The final installment of the Ultimate Tournament of Champions, this episode features big names Brad Rutter and Ken Jennings as they continue to dominate the Jeopardy stage. The two battle it out alongside Jerome Vered, another legendary winner, and compete for the title of Ultimate Jeopardy Champion. 

Roger Craig owns the stage in this Tournament of Champions final, with an impressive streak of daily doubles serving to multiply his winnings and stun viewers. This moment is one of the most fun in history, with Buddy Wright and Tom Nissley providing the perfect onstage chemistry to keep this episode interesting. 

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Alex Trebek’s last-ever performance as Jeopardy’s host, this episode is undoubtedly one of the show’s most bittersweet. However, despite its heart-wrenching moments, this episode is a can’t-miss for your next rewatch. Trebek stays charming, talented, and humorous to his very last moment on Jeopardy, rounding out our list of the 20 best Jeopardy episodes to rewatch.

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