Jessica and I watch one or two episode of "Jeopardy!" almost every night, and I've long wondered what it's like to be on the show. Not just whether I could win or not, but about the whole experience. A quick Google search revealed two-game champion Karl Coryat's "Jeopardy!" story, with some insight from a real player's perspective.
Someone calling it/him/herself "Jeobirdy" also has an extremely annoying account of how contestants are chosen and later contacted to appear. I don't think I've ever waded through more painful nonsense for just a few nuggets of information.