George Clooney is betting he's going to be a winner, and a loser this weekend. The 46 year-old Best Actor nominee for the film Michael Clayton recently swore to Time (TMX)magazine that he's never lost an Oscar betting pool. So, to make sure he continues to collect winnings, on Sunday he'll be betting on Daniel Day-Lewis, to take Best Actor for There Will Be Blood(VIAB), not himself. “There is no way Daniel Day Lewis won't win,” says Clooney, who won an Oscar in 2005 for his supporting performance in Syriana.

Place your bets! Oscar weekend is the Super Bowl of celebrity awards shows. “The amount of money [bet on] the Oscars, can reach a few million,” says Benjamin Eckstein, oddsmaker and president of America’s Line in Las Vegas. Betting with real money, Eckstein says, is a grey area. For office and party pools, wager with prizes. Overseas, online betting is less regulated, as long as you do not use a credit card. “The real money is in betting overseas," says Eckstein. "It’s not specifically legal or illegal. Just don’t use your credit card. That’s what the law says." Instead, Eckstein suggests placing wagers via bank drafts or Western Union. In the UK legal bookmakers include  www.Ladbrokes.com and William Hill www.willhill.com. 

If you are interested in betting for entertainment purposes, there are two ways to run a pool, says film expert Stu VanAirsdale, editor of The Reeler. Viewers can run a straight Oscar pool that lists every nomination in the 72 categories, or just have participants choose the top five or six categories and get a little more creative with proposition wagers.

Proposition bets can really jazz things up during the lengthy lifetime achievement speeches. This year VanAirsdale's party goers will bet on the memoriam montage, the sequence of stars who have passed away since the previous Oscars. “The questions range from who will be first, to who will be featured last,” says VanAirsdale. "The last person in a memoriam is the most famous and beloved. Will be it be Heath [Ledger] or Ingmar Bergman?" The less likely person to be chosen, the more points you would get if they win. "It’s not supposed to be morbid; it’s a fun contest to spice up the pool,” says VanAirsdale.

Another proposition bet Eckstein suggests, is an over under. “We do an over under on how many times the camera will pan to Jack Nicholson. This year we have it at 4.5 times. Go under 4.5 or over 4.5." Eckstein is also taking bets on whether Paris Hilton's Oscar ban will stand. "Will she get in or not? We think the odds are good since she is Paris Hilton. I am thinking it’s 5 to 1.” (When reading odds, explains Eckstein, read them in the opposite direction. “Read it backwards like Hebrew. We say it is 2:5 heavily in favor of No Country for Old Men for Best Picture. [That means] you put up five dollars to bet and get two additional dollars if you win.”)

Back to Clooney's bet. Day-Lewis odds are 1:8, a lot more likely than Clooney who is an 8 to 1 shot. For Eckstein, the best bet is obvious. “I’d bet dinner that Daniel Day Lewis will win.”