Roger Craig
Craig is our most recent record-setter. He may not have hit the million mark, but on an episode that aired Sept. 14, this grad student became the biggest one-day winner in the history of the show, beating out a $75,000 winner from the past.He wrote down the correct response and won the Final Jeopardy bet. How much did he win over a seven-day period?John Carpenter
In 2000, Carpenter (not this award-winning legend) went from a loathsome profession to becoming the show's first millionaire. He gave the winning answer to this question. After the win, he appeared on morning and late-night TV, shared a privilege enjoyed by the likes of Brad Pitt and Barack Obama and co-wrote a book. He reappeared on the show in 2009.Kevin Olmstead
Olmstead is the show's biggest winner to date. He answered the final question about a Russian inventor. How much did he win? The tree-hugger went on to help students become winners, too.Ken Jennings
The former thorn in Alex Trebek's side had the show's longest winning streak. (Meet the contestant who broke it.) He earned more than this much from the show, thanks to a one-time comeback.And when he was done with that show, he won on another (how much did he win?). Jennings watched the show growing up on the other side of the world and honed his skills on a college quiz bowl team. Now, you can try to beat the author at his own game.
Brad Rutter
Rutter won not only cash and titles from the show, but matching wheels as well. The Lancaster, Pa., college dropout is no stranger to quiz shows, and before hitting the jackpot, he earned cash dealing with a different kind of record.
Ed Toutant
Hailing from this capital city, Toutant is no stranger to keeping it weird. Indeed, his path to winning a ton of dough was a strange one. Toutant, who'd visited the trivia world before, got cut from the show halfway through. But after quibbling over his answer about the oddest subject ever, Toutant was invited back in an unprecedented move and ultimately won big.Adam Rose
Rose was the first to hit it big when the daytime show switched things up a bit in 2008. And he didn't just win cash -- he sailed away with a car and gadgets, too (no wonder he's making this face).The California teacher later graced the same stage as Janet Jackson and got some media mogul love. He then put his winnings to super-duper good use.