The Most Surprising Celebrity Jeopardy! Champions

Back in 1992, the first ever Celebrity Jeopardy! episode aired, hosted by the late great Alex Trebek and pitting Carol Burnett, Donna Mills, and the late Regis Philbin against each other. Burnett ended up winning the game, which would spawn a series of celebrity tournaments, not to mention one of the most legendary recurring Saturday Night Live sketches of all time. Since then, many celebrities have come and gone, some embarrassing themselves, like Wolf Blitzer's devastating failure, and some surprising the world. 

Jeopardy! is a funny game. The best players do not necessarily have to be the brightest in the room, they just have to be quick on the buzzer and possess a wealth of trivial knowledge. Since we know the celebrity contestants as actors, athletes, or TV personalities outside of the show, we may not expect them to be equipped with so much information. And that opens the door for shocking performances. So we went through all of the famous winners throughout the show's history and narrowed it down to the most surprising Celebrity Jeopardy! champions.

In 1992, Cheech Marin bested actors Steven Weber and Alan Rachins to be named champion in the first run of Celebrity Jeopardy! during the show's ninth season. One half of the legendary Cheech & Chong duo, Marin was thrilled with his victory. "I always wanted to go on that program and I just wailed," he told the South Florida Sun Sentinel, who called him an 'ex-hippie comic.' "I've gotten more recognition out of Jeopardy! than probably anything I've done." Marin's stoner comedy past doesn't quite make him a prime candidate for Jeopardy! success, but successful he was.

In 2010, Marin returned to the Jeopardy! stage, this time for the Million Dollar Celebrity Invitational Tournament. In his first game, the actor beat CNN anchor Anderson Cooper. "No offense, but every time I tell people that I lost to you, they seem surprised," Cooper told Marin in an CNN interview. "I think having watched some of your movies in the past, they maybe think like your synapses wouldn't be so fast, but they don't realize how smart you are and how quick you are." In that tournament, Marin would go on to make the finals before losing to a very formidable opponent.

Few Jeopardy! players remain undefeated. Even Ken Jennings lost. But comedian and actor, Michael McKean is one of the few with an untarnished record on the show. Best known for his early roles on Laverne & Shirley and This Is Spinal Tap, McKean might be thought of silly if that's all you knew about him. But the actor has come a long way since his comic days. In total, he appeared on the show six times, winning every appearance — and being the son of a librarian probably didn't hurt him on his journey to becoming the winningest Celebrity Jeopardy! contestant in history.

McKean made his first appearance in 1999, winning over actors Richard Kind and Camryn Manheim. In 2006, he obliterated actor Hill Harper and U.S. Secretary of Education Margaret Spellings. It was then-news anchor Soledad O'Brien and basketball star Kareem Abdul-Jabbar who McKean creamed in 2009. Finally, during the Jeopardy! Million Dollar Celebrity Invitational Tournament, McKean won all three rounds to take home the $1 million for his charity, the International Myeloma Foundation. In the final two games of the tournament, McKean took down actors Jane Curtin and Cheech Marin. McKean turned out to be as humble as he was proficient at triva, saying (via Mass Live), "It was really daunting to play against such smart people. Everyone was really fast on the button!"

Fans of opposing teams might try to lump quarterback Aaron Rodgers into the dumb jock stereotype. Even the Cheeseheads, who watched him become one of the best players in the NFL, might not automatically think the star Green Bay Packers quarterback is as smart as he really is. Yet, back in 2011, The New York Times had already revealed Rodgers "A-minus average and an SAT score of 1310." Rodgers also scored exceptionally high on the Wonderlic Test, which helps determine a player's aptitude and cognitive abilities.

In 2015, Rodgers showcased his smarts by winning Celebrity Jeopardy!, trouncing entrepreneur and reality TV star Kevin O'Leary and retired astronaut Mark Kelly in the process. He ended up winning $50,000 for his charity, the Midwest Athletes Against Childhood Cancer Fund. According to his teammates, his win was just another example of his brains. "He is a genius. Aaron Rodgers is a genius," Datone Jones said on NFL Network's NFL HQ the following year. "He's a smart guy. ... That's who he is in the locker room. He's a guy who's going to challenge you mentally. ... He's extremely smart. He knows the defense. He teaches his receivers the defense."

As one half of the popular duo Penn and Teller, Penn Jillette may be one of the most recognizable illusionists in the world, but there was no magic involved in his Celebrity Jeopardy! win. There was some sleight of mouth, however, as Jillette accidentally gave the wrong answer in a Daily Double question but quickly corrected himself to fix the mistake and stay within the rules. In the end, the entertainer won handily against actor Zachary Quinto and designer Cynthia Rowley in their 2015 game.

For Jillette, this win righted the ship after an unsuccessful string of celebrity appearances on TV game shows, including a second place finish on Celebrity Apprentice and two premature exits on Who Wants to Be a Millionaire. "I have played a lot of television games and have lost every single one with the exception of this," he told the Jeopardy! Crew. "That was, I believe, a theatrical decision, a dramatic decision. I wanted to lose, lose, lose, lose, lose. The one that matters, I won." Jillette donated his $50,000 winnings to Opportunity Village, which he notes, is "Elvis' favorite charity." 

Aisha Tyler has played a paleontologist on Friends, she's been the host of multiple shows, including The Talk for six seasons, and she's a talented voice actress. She's also a Celebrity Jeopardy! champion, which might be surprising for some fans. Tyler claimed victory in 2009 against Weeds actor Elizabeth Perkins and Tom Bergeron, the former host of America's Funniest Home Videos and Dancing with the Stars. In 2010, she returned to the show only to lose to finalist Cheech Marin.

Just listening to Tyler speak, it's clear that she has strong wit and eloquence, but she's also well-educated and exceptionally intelligent. In an interview with HoboTrashCan, she revealed that she's multilingual. "I speak fluent French. I'm a big Francophile," she said, adding, "I also speak functional Russian and functional Swahili." The graduate of Dartmouth College was once on the lawyer pathway before deciding to pursue her career as a comedian. There's even rumors about her having a 150+ IQ, which puts her in the genius range.

If you've ever watched television, it's likely you've spotted Wayne Brady in one of his countless gigs. Most famous for performing on the improvisational comedy show, Whose Line Is It Anyway?, or his talk show, The Wayne Brady Show, the multi-talented actor also hosted Don't Forget the Lyrics! and the reboot of Let's Make a Deal. 

In 2001, Brady made his first appearance on Celebrity Jeopardy! After jumping out to an early lead against actors Dana Delaney and Eric Idle, Brady faltered in Final Jeopardy and was overtaken by Idle. The winning Monty Python alum has still not let his opponent forget it either, ribbing him on Twitter and causing Brady to ask him for a rematch. The comedian would get his chance at redemption in Celebrity Jeopardy! in 2003, returning to the stage to face off against Ashton Kutcher and Vivica A. Fox. This time, he would be named champion, annihilating the competition by more than $23,000.

Even though Neil Patrick Harris got his big break playing a boy genius on Doogie Howser, M.D., and then solidified his household name status playing the evil genius Barney Stinson on How I Met Your Mother, fans would be forgiven for not knowing he's also a trivia whiz. But Harris proved exactly that when he etched his name in the win column on Celebrity Jeopardy! in 2006, taking down actors Bebe Neuwirth and James Denton.

When he returned for the 2010 tournament, he was even more prepared. "I didn't drink as much as I usually do last night," he joked of his pregame regime. "I went through like a fifth, and a bottle and a half of Goldschläger. So I feel a little sharper than usual." His quarterfinal game went off without a hitch, and he won rather easily over author and actor Hill Harper and basketball analyst Rebecca Lobo. In his semifinal match, however, Harris was matched up against Cheech Marin and Jane Kaczmarek, two of the best to ever do it. He came second and took home $25,000 for his charity, Food on Foot.

A generation of fans out there hold Jane Kaczmarek in very high regard. Playing Lois on Malcolm in the Middle, the actor became one of the most beloved characters on television. But it's quite likely that her brain power has flown under the radar, particularly since her most memorable character's intelligence was anything but renowned. Yet, Kaczmarek is pretty remarkable in real life. She earned a graduate degree from Yale and she studied classical music at UCLA before hitting it big in acting. She also demonstrated that she's one of the best Celebrity Jeopardy! contestants.

In 2006, Kaczmarek won her first game against MLB pitcher Curt Schilling and actor Doug Savant. After her win, she said it was a dream come true. "I think I have had two dreams in my life: to win Jeopardy! and to win the Miss America pageant," she told the Jeopardy! crew. "So I think if I can shave about forty years off me, and about forty pounds, I might also have a shot at Miss America!" In 2009, she was brought back for the Million Dollar Celebrity Invitational, in which she won her quarterfinal but lost to Cheech Marin in the semifinals.

Andy Richter is best known for being the host's sidekick on Late Night with Conan O'Brien and Conan. In Jeopardy! lore, however, Richter is a bit of a legend unto himself. In his first appearance in 1999, he crushed the competition. "I've always called you Mr. Knowledge behind your back," O'Brien told him after his first victory, adding, "You know about stuff that no one has to know about." Richter agreed: "Boy, I've cornered the market on crap knowledge." At the time, the comic held the third-highest score in Celebrity Jeopardy!, a record he would absolutely destroy the next time he took the stage.

In 2009, Richter competed against actor Dana Delaney and journalist Wolf Blitzer during the quarterfinals of the Million Dollar Celebrity Invitational. When the game was done, the Jeopardy! prodigy had $68,000, nearly three times his score from the first game and by far the highest of all time for celebrities. Unfortunately, we never got to see what Richter could do in the semifinals as he was replaced by Isaac Mizrahi due to a scheduling conflict. "I have a lot of incredibly shallow knowledge about a lot of things," he said in a humble interview with The A.V. Club, adding, "Being that great on Jeopardy! doesn't necessarily mean you're smart, it just means that you have a lot of, like, little post-it notes of bullsh*t floating around in your head."