Bill Simmons Whitehead's Grantland boss tried out a similar (read: identical) conceit back in 2006, just as the number of players hit an all-time high of more than 11,000. It ended with Simmons getting bounced on the first day and ESPN effectively eating the $10,000 entry fee. The column was fine, but not the kind of thing you'd like to pay for more than once every five years.
Matt Damon and Edward Norton They played in 1998, before the Internet poker boom, to promote Rounders. Neither made it past the first day, though the circumstances of Damon's ouster were memorable enough to make the trivia section of the film's IMDB page. (Damon had pocket aces, but busted out when former world champion Doyle Brunson drew pocket aces.) Norton's elimination doesn't receive any additional explanation, which says it all.
Montel Williams He gave stunt contenders reason for optimism in 2007, when he briefly held the overall chip lead. Then bad luck, helped along by some "spectacularly bad calls," at least according to the AP, set in.
Tobey Maguire The one that got away, even before he emerged as a prominent figure in the still-unfolding investigation into high-stakes Hollywood poker games. He lasted until day three in 2007, a remarkable achievement that didn't match poker analyst Phil Gordon's even loftier expectations for the Spiderman star. "He's got the perfect disposition at the table, he's studied a lot, he plays in huge cash games," Gordon said. "He definitely has a game that could get deep, maybe even final table, maybe even win."