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The Regular Jobs of 10 Legendary Game Show Champions

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Getty Images

Near the end of the 20th century, game shows suddenly became big event programming again. With the success of Who Wants to Be a Millionaire? came a wave of copycats and some unprecedentedly huge cash prizes–not to mention a type of overnight celebrity not seen since the late 1950s and the original Twenty One. In 2004, Ken Jennings went on an incredible, record-destroying 74-game run as Jeopardy! champion, which finally came to its end ten years ago Sunday*. Jennings and other whip-smart men and women made a fortune, changing their financial situations. This is a look at the backstories and jobs of the top ten biggest game show winners of all time.

1. BRAD RUTTER — RECORD STORE CLERK ($4,555,102 In Total Winnings)

Brad Rutter is the all-time game show money maker, mostly thanks to his sweeping five-day appearance on Jeopardy! in 2001 (before the five-game limit was lifted), winning the show's Tournament of Champions and Million Dollar Masters extravaganzas in 2002, and this year's Battle of the Decades. The only time Rutter ever lost on Jeopardy! was when he lost to Watson, the computer, in the 2011 IBM Challenge. He claimed in a 2005 interview to have a "flypaper memory," which helped him develop a love and mastery of trivia while playing on his high school's quiz bowl team. A self-proclaimed "slacker" with a poor attention span, Rutter dropped out of Johns Hopkins University and worked at a Coconuts record store in his hometown of Lancaster, Pennsylvania. He continued to work there even after winning on Jeopardy! the first time around, because he figured he would make more money once he got the inevitable invite to the Tournament of Champions.

2. KEN JENNINGS — SOFTWARE ENGINEER ($4,123,414.29 In Total Winnings)

Jennings had a chance to surpass Rutter in total winnings, but he made a paltry $100,000 on a recent episode of Who Wants to Be a Millionaire?. The Jeopardy!, Are You Smarter Than a 5th Grader?, Grand Slam, and 1 vs. 100 participant grew up watching Jeopardy! "religiously" on the Armed Forces Network in Korea and Singapore, where his father was a lawyer. He graduated with a degree in both English and computer science from BYU, where he captained their quiz bowl team. When Jennings got The Call in 2004 to fly out to Culver City, he was a software engineer at a Salt Lake City health care staffing company.

3. ANDREW KRAVIS — LAW STUDENT ($2,656,550 In Total Winnings)

The Michigan-born Kravis made the bulk of his winnings on 2013's NBC primetime game show Million Second Quiz, which awarded the biggest cash prize in game show history to its winner. Kravis earned $2.6 million from the Ryan Seacrest-hosted program, but got his game show start when he was 13 years old on Jeopardy!'s 2002 Teen Tournament. Kravis won $5,000 as a wildcard semifinalist, saying then that he intended to be a teacher when he grew up. When Kravis did grow up and won the big bucks 11 years later, he was a recent graduate of Columbia Law School, and was about to begin a fellowship at a legal organization that works for LGBT rights.

4. KEVIN OLMSTEAD — PROJECT ENGINEER ($2,207,000 In Total Winnings)

Kevin Olmstead was more than ready to win big on a trivia show—he participated in quiz bowls while attending the University of Michigan, and helped start a company that wrote questions for quiz bowls in colleges and businesses. On an edition of Millionaire with a much bigger grand prize than usual, Olmstead knew the answer to the $2.18 million question that asked for the inventor of a mass-produced helicopter. The trivia writer admitted that he kind of got lucky drawing a question about engineering history—his day job was senior project engineer at a global consulting firm.

5. ED TOUTANT — ENGINEER ($1,871,401 In Total Winnings)

Ed Toutant might somehow be both the luckiest and unluckiest game show contestant of all time. Things started off innocently enough with a two-day appearance on Jeopardy! in 1989, where he won $11,401. In 1991, he left empty handed on a syndicated game show called The Challengers, but the episode didn't air in most of the country because it coincided with the start of the Gulf War. Ten years later, he got the $16,000 question on Millionaire wrong, and this time his failure made it to TV. On ABC. Right after its coverage of the Super Bowl. But it turned out that the question was flawed, so the Austin, Texas IBM engineer was invited back to the show, where this time the grand prize was up to $1.86 million. This time, he won it all. Toutant remained at his engineering job long enough to turn traitor towards his fellow human contestants, helping IBM make Watson into a literal Jeopardy!-winning machine that defeated both Rutter and Jennings in 2011.

6. ASHLEE REGISTER — REGISTERED NURSE ($1,795,000 In Total Winnings)

Register became the highest-winning female game show contestant in U.S. history when she won $1,795,000 on the short-lived Duel, which combined trivia with poker. The registered nurse from Florida with a B.S. in microbiology won when her opponent didn't know that a gallon of water weighs more than a gallon of crude oil or vegetable oil.

7. DAVID LEGLER — NAVY LIEUTENANT ($1,765,000 In Total Winnings)

Legler earned his fortune after winning six times on the 2000 version of Twenty One. David received an undergraduate degree in engineering at the University of Chicago, and two weeks after his victory expressed his desire to finish his studies at their business school to earn his MBA. However, as a U.S. Navy Lieutenant, he still had an obligation to recruit officers for submarines and nuclear surface ships through November.

8. CURTIS WARREN — AIR TRAFFIC CONTROLLER ($1,546,988 In Total Winnings)

Having already pocketed $410,000 from Greed, Warren earned another $1,000,000 when he knew immediately that McHale's Navy, Dragnet, The Flintstones, and The Beverly Hillbillies were TV shows that were made into movies, and Hawaii Five-O, Melrose Place, Miami Vice, and Bewitched were not (as of February 11, 2000 anyway). Warren also made some money on the '80s show Sale of the Century, and on Win Ben Stein's Money, where host Jimmy Kimmel made fun of his "Duran Duran" hair. Less than two weeks following his Greed appearance, Warren was quoted in the Los Angeles Times as an outspoken air traffic controller union president from Cathedral City, California.

9. JOHN CARPENTER — PIZZA DELIVERY BOY ($1,250,000 In Total Winnings)

John Carpenter was the first person to ever win on Who Wants to Be a Millionaire?. He graduated from Rutgers University with a degree in economics and worked summers at an amusement park and on an assembly line packing Chap Stick tubes in boxes. After graduation, he was a Domino's delivery boy for six months, at one point getting robbed at gunpoint while on the job. Soon after, he became an IRS employee. (When he was asked in 2009 why he continues to work, Carpenter pointed out that he paid $400,000 in federal, state, and local taxes in 1999, the year he won). Growing up, Carpenter spent a lot of time playing games like Trivial Pursuit and 20 Questions, and watched copious amounts of Jeopardy! with his two brothers and his mother and father, an administrative assistant for the Massachusetts Audubon Society and a computer program analyst. Carpenter's friend and IRS co-worker told People in their cover story on Carpenter that the game show legend finished New York Times crosswords every day at lunch, and before becoming famous was known around the office as the "King of Useless Trivia."

10. ADAM ROSE — PRE-SCHOOL TEACHER ($1,153,908 In Total Winnings)

Rose won both showcases, plus a sweet bonus of one million dollars, on a 2008 episode of The Price is Right $1,000,000 Spectacular for managing to accurately guess the actual retail price of a Cadillac XLR convertible within $1,000. Rose was a California teacher making less than $11 an hour at the time.

* The original version of this post incorrectly stated the end date of Ken Jennings' amazing run. We apologize for short-changing him.

Ben Leuner, AMC
You Can Cook (Food) With Bryan Cranston and Aaron Paul in the Original Breaking Bad RV
Ben Leuner, AMC
Ben Leuner, AMC

A new contest is giving Breaking Bad fans the chance to cook a meal with Walter White and Jesse Pinkman. A new charity fundraising campaign is sending one lucky fan and a friend out to Los Angeles to celebrate the 10th anniversary of Breaking Bad’s premiere with the stars themselves—Bryan Cranston, Aaron Paul, and that beat-up RV.

“That’s right, the real Walter White and Jesse Pinkman will join you in The Krystal Ship to whip up some delicious food, take tons of pictures, and bond over the most addicting show ever made,” the contest’s page on the charity fundraising site Omaze trumpets.

All you have to do to throw your (porkpie) hat in the ring is break out your wallet and donate to a good cause. Every dollar you donate to the contest through Omaze is basically a raffle ticket. And the more you donate, the better your odds are of winning. Each dollar donated equals 10 entries, so if you donate $10, you have 100 chances, if you donate $25, 250 chances, etc. At higher donation levels, you’ll also get guaranteed swag, including T-shirts, signed set photos by Cranston and Paul, props and scripts from the show, and more.

Technically, you can enter without donating, but don’t be a jerk—it’s for the kids. The proceeds from the contest will go to the National Center for Missing and Exploited Children and the Kind Campaign, an anti-bullying charity.

The contest winner will be announced around September 12, and the big event will take place on September 15.

Donate to win here. The contest ends at 11:59 p.m. PT on August 30.

Zach Hyman, HBO
10 Bizarre Sesame Street Fan Theories
Zach Hyman, HBO
Zach Hyman, HBO

Sesame Street has been on the air for almost 50 years, but there’s still so much we don’t know about this beloved children’s show. What kind of bird is Big Bird? What’s the deal with Mr. Noodle? And how do you actually get to Sesame Street? Fans have filled in these gaps with frequently amusing—and sometimes bizarre—theories about how the cheerful neighborhood ticks. Read them at your own risk, because they’ll probably ruin the Count for you.


According to a Reddit theory, the Sesame Street theme song isn’t just catchy—it’s code. The lyrics spell out how to get to Sesame Street quite literally, giving listeners clues on how to access this fantasy land. It must be a sunny day (as the repeated line goes), you must bring a broom (“sweeping the clouds away”), and you have to give Oscar the Grouch the password (“everything’s a-ok”) to gain entrance. Make sure to memorize all the steps before you attempt.


Sesame Street is populated with the stuff of nightmares. There’s a gigantic bird, a mean green guy who hides in the trash, and an actual vampire. These things should be scary, and some fans contend that they used to be. But then the creatures moved to Sesame Street, a rehabilitation area for formerly frightening monsters. In this community, monsters can’t roam outside the perimeters (“neighborhood”) as they recover. They must learn to educate children instead of eating them—and find a more harmless snack to fuel their hunger. Hence Cookie Monster’s fixation with baked goods.


Big Bird is a rare breed. He’s eight feet tall and while he can’t really fly, he can rollerskate. So what kind of bird is he? Big Bird’s species has been a matter of contention since Sesame Street began: Big Bird insists he’s a lark, while Oscar thinks he’s more of a homing pigeon. But there’s convincing evidence that Big Bird is an extinct moa. The moa were 10 species of flightless birds who lived in New Zealand. They had long necks and stout torsos, and reached up to 12 feet in height. Scientists claim they died off hundreds of years ago, but could one be living on Sesame Street? It makes sense, especially considering his best friend looks a lot like a woolly mammoth.


Oscar’s home doesn’t seem very big. But as The Adventures of Elmo in Grouchland revealed, his trash can holds much more than moldy banana peels. The Grouch has chandeliers and even an interdimensional portal down there! There’s only one logical explanation for this outrageously spacious trash can: It’s a Doctor Who-style TARDIS.


Dust off your copy of The Republic, because this is about to get philosophical. Plato has a famous allegory about a cave, one that explains enlightenment through actual sunlight. He describes a prisoner who steps out of the cave and into the sun, realizing his entire understanding of the world is wrong. When he returns to the cave to educate his fellow prisoners, they don’t believe him, because the information is too overwhelming and contradictory to what they know. The lesson is that education is a gradual learning process, one where pupils must move through the cave themselves, putting pieces together along the way. And what better guide is there than a merry kids’ show?

According to one Reddit theory, Sesame Street builds on Plato’s teachings by presenting a utopia where all kinds of creatures live together in harmony. There’s no racism or suffocating gender roles, just another sunny (see what they did there?) day in the neighborhood. Sesame Street shows the audience what an enlightened society looks like through simple songs and silly jokes, spoon-feeding Plato’s “cave dwellers” knowledge at an early age.


Can a grown man really enjoy taking orders from a squeaky red puppet? And why does Mr. Noodle live outside a window in Elmo’s house anyway? According to this hilariously bleak theory, no, Mr. Noodle does not like dancing for Elmo, but he has to, because he’s in hell. Think about it: He’s seemingly trapped in a surreal place where he can’t talk, but he has to do whatever a fuzzy monster named Elmo says. Definitely sounds like hell.


Okay, so remember when Animal chases a shrieking woman out of the college auditorium in The Muppets Take Manhattan? (If you don't, see above.) One fan thinks Animal had a fling with this lady, which produced Elmo. While the two might have similar coloring, this theory completely ignores Elmo’s dad Louie, who appears in many Sesame Street episodes. But maybe Animal is a distant cousin.


Cookie Monster loves to cram chocolate chip treats into his mouth. But as eagle-eyed viewers have observed, he doesn’t really eat the cookies so much as chew them into messy crumbs that fly in every direction. This could indicate Cookie Monster has a chewing and spitting eating disorder, meaning he doesn’t actually consume food—he just chews and spits it out. There’s a more detailed (and dark) diagnosis of Cookie Monster’s symptoms here.


Can a vampire really get his kicks from counting to five? One of the craziest Sesame Street fan theories posits that the Count lures kids to their death with his number games. That’s why the cast of children on Sesame Street changes so frequently—the Count eats them all after teaching them to add. The adult cast, meanwhile, stays pretty much the same, implying the grown-ups are either under a vampiric spell or looking the other way as the Count does his thing.


Alright, this is just a Dave Chappelle joke. But the Count does have a cape.


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