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.