The 10 Best Celebrity Jeopardy! Contestants Ever

Although Jeopardy! first aired in the 1960s, it wasn't until nine years into the Alex Trebek-hosted edition of the series, on October 26, 1992, that the show first kicked off a week of celeb contests with comedy legend Carol Burnett, talk show host Regis Philbin, and Knots Landing star Donna Mills as the initial lineup. Burnett eked out a win with a relatively meager $2,900 winning.

Over the intervening thirty years, some celebrities have fallen flat on their face (Shark Tank's Kevin O'Leary, your failure will always be memorable, and Saturday Night Live got fifteen sketches out of the premise that the celebs were otherworldly stupid). But there have also been quite a few celebs who managed to deliver under those studio lights, nailing the Daily Doubles and wagering smartly, ending up with some gaudy amounts when all was said and done.

We've combed through three decades' worth of celebrity Jeopardy episodes and found the ten most dominant performances. It should be noted that in November of 2001, Jeopardy changed the dollar values on its questions, effectively vanquishing all previous top performing celebrities prior from this list. So after we rank the ten highest-winning performances, we'll also list the ten highest-winning celebrity performances from the pre-doubling era.

The Ten Best Celebrity Jeopardy Games of All Time

Andy Richter
Cash winnings: $68,000
Date: September 17, 2009

The Million Dollar Celebrity Invitational that played out over late 2009 and early 2010 gathered some of the best-performing celebs from the show's history and let them battle it out in a rather epic tournament. Five of the ten all-time best celebrity Jeopardy performances come from that tournament, including this one, which was the very first quarterfinal matchup. This was the game in which CNN's Wolf Blitzer rather infamously finished the Double Jeopardy round $4,600 in the hole (under normal circumstances, he wouldn't have been allowed to participate in Final Jeopardy, but in the celebrity game the show gives players a pity $1,000 to wager because it's for charity). But the real story was Andy Richter's dominance. The comedian who was famous for being Conan O'Brien's sidekick proved himself to be a quiz-show master. In the Jeopardy round, Richter swept the "2-Letter Words" category, in Double Jeopardy he bet big on a Hemingway question for the Daily Double and won, and in Final Jeopardy, he wagered $29,000 out of a possible $39,000 to land at the all-time highest single-game total for a celebrity.

Pat Sajak
Cash winnings: $55,300
Date: January 21, 2010

This was another Million Dollar Celebrity Invitational quarterfinal. The Wheel of Fortune host was up against Weeds star Elizabeth Perkins and Desperate Housewives husband Doug Savant. He took a commanding lead after the Jeopardy round, and although Perkins was able to score big on a Daily Double to keep her within $5,000 heading into Final Jeopardy, she flubbed the final question about Charlie Brown, while Sajak got it right and landed at that gaudy dollar amount.

John Berman
Cash winnings: $42,900
Date: May 13, 2015

Up against Mo Rocca and Wendi McLendon-Covey, CNN anchor John Berman was actually in second place coming out of the Jeopardy round. By the end of Double Jeopardy, he had been able to claw out a $1,600 lead over Rocca, and when all three were able to identify this quote — "Just arrived at the ocean's deepest pt. Hitting bottom never felt so good" — as having been from James Cameron, Berman wagered just enough to score a victory and the third-highest celebrity total in show history.

Mo Rocca
Cash winnings: $41,600
Date: May 13, 2015

In the best celebrity performance by someone who didn't win their game, CBS Sunday Morning correspondent and Daily Show alum Mo Rocca battled with John Berman, bet big on a Daily Double ("It precedes 'Special' & 'Train To Georgia' in song titles") and won, and aced his Final Jeopardy answer, only to finish $1,300 shy of first place.

Michael McKean
Cash winnings: $38,800
Date: November 21, 2

Cumulatively, Michael McKean might be the best celebrity Jeopardy player of all time. He alone holds three of the ten best celebrity performances in show history and is one of the show's most reliable famous faces. In this matchup, McKean was up against CSI: NY actor Hill Harper and the then-current U.S. Secretary of Education Margaret Spellings, and it was a blowout from the start. Michael ran the table on the Stonehenge category in single Jeopardy, and even with Spellings hitting both of the Daily Doubles, McKean ended Double Jeopardy as the runaway leader. He still bet big enough on Final Jeopardy to set what was then the all-time celebrity high-water mark.

Jane Curtin
Cash winnings: $37,900
Date: April 16, 2010

In the quarterfinals of the Million Dollar Celebrity Invitational, former Saturday Night Live and 3rd Rock from the Sun took on Isaac Mizrahi and CCH Pounder. Mizrahi stayed close throughout, but thanks to a bold wager in Final Jeopardy and some critical knowledge of the life and career of Laurence Olivier, Curtin cruised into the semifinals.

Michael McKean
Cash winnings: $37,100
Date: May 4, 2010

On to the semifinals of the Million Dollar Celebrity Invitational, where McKean faced off against Isaac Mizrahi (back again!) and The Nanny's Charles Shaughnessy. It was a close contest throughout, with each winning one Daily Double and all three separated by just $5,000 going into Final Jeopardy. McKean and Mizrahi both nailed the Final Jeopardy question ("In 1953 it became the only state whose official song was written for a Broadway musical"), but McKean bet enough to advance to the finals with a gaudy dollar amount.

Chris Matthews
Cash winnings: $32,400
Date: May 1, 2003

The former MSNBC host took on Gilmore Girls star Lauren Graham and ER's Paul McCrane in a very competitive matchup. Graham ended the Jeopardy round in the lead, but Chris went 4/5 in the Historic Moments category and grabbed the lead heading into Final. And with a ton of confidence in a category that played to his strengths — Government Agencies — he bet his entire $16,200 amount on a question that was actually as much about entertainment as it was about government. He knew that that CIA was where Emma Peel's leather pants & Maxwell Smart's shoe phone were displayed, and thus doubled up and prevailed.

Hal Sparks
Cash winnings: $32,000
Date: April 28, 2003

Queer as Folk star Hal Sparks went up against Trading Spaces host Paige Davis and Julie Bowen, who at the time was starring as the love interest on NBC's Ed. It was a tremendously close contest, with Sparks hitting two of the three Daily Doubles, and Bowen going 4/5 on the Oscars category in Double Jeopardy. Bowen had the lead heading into Final — a question about the Queen Mary — but Sparks bet everything he had, and Bowen bet too timidly, and thus was able to leapfrog her and take the win.

Michael McKean
Cash winnings: $31,600
Date: May 6, 2010

One last time into the Million Dollar Celebrity Invitational. This was day 1 of the two-day final that pitted McKean against Jane Curtin and Cheech Marin, who was doing all pot smokers proud that day. McKean ran the "That's Handy" category in single Jeopardy, but Curtin hit both Daily Doubles in Double Jeopardy, and was thus only $2,600 behind McKean heading into Final. There, knowing it was a two-day final, they each bet relatively conservatively — $10,000 apiece, about half of their respective totals — on a question about Moby Dick. If McKean had been more aggressive, this game would rank a lot higher on this list, but he's already on here three times, so it feels rude to gripe. McKean would go on to win the entire Million Dollar tournament the next day.

The Ten Best Celebrity Jeopardy Games Before the Dollar Amounts Were Doubled

Andy Richter: $24,000 (November 16, 1999)
Jon Stewart: $23,000 (November 17, 1999)
Mark McEwen: $21,700 (April 28, 1997)
Bob Costas: $20,000 (March 22, 1999)
Thomas Gibson: $19,400 (February 5, 1999)
Sam Waterston: $18,800 (May 1, 1997)
Jeff Greenfield: $18,000 (April 12, 1999)
Jerry Orbach: $17,000 (November 11, 1993)
Peter Krause: $17,000 (November 19, 1999)
Wallace Langham: $16,800 (March 29, 1999)

That's right — Andy Richter holds the record in both the pre- and post-prize doubling eras. Truly the Celebrity Jeopardy GOAT. The Serena Williams of the celebrity circuit. Some other trends of note: news people/studio host types have historically done very well here, with Stewart, Costas, Greenfield, and McEwan representing the four corners of televised news (politics, sports, weather, and parody). Also let's hear it for Law & Order, whose stars Jerry Orbach and Sam Waterston were among the best performances of all time.

Celebrity Jeopardy! premieres on ABC September 25th at 8:00 PM ET.

People are talking about Jeopardy! in our forums. Join the conversation.

Joe Reid is the senior writer at Primetimer and co-host of the This Had Oscar Buzz podcast. His work has appeared in Decider, NPR, HuffPost, The Atlantic, Slate, Polygon, Vanity Fair, Vulture, The A.V. Club and more.