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Nate Silver, Joe Scarborough Bet on Election & More Wild Wagers (Photos)

Will it be Nate Silver or Joe Scarborough? From Clooney to Romney, a look at high-stakes bets—and who won.

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Nate Silver bet Joe Scarborough $2,000 that Obama will beat Romney on Election Day. See other big gambles from George Clooney, Bruce Willis, Leonardo DiCaprio and more.

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Nate Silver vs. Joe Scarborough

Proving he would put his money where his stats are, FiveThirtyEight blogger Nate Silver made a very public wager this week with Morning Joe co-host Joe Scarborough about the presidential election. “@JoeNBC: If you think it’s a toss-up, let’s bet,” Silver tweeted on Thursday. “If Obama wins, you donate $1,000 to the American Red Cross. If Romney wins, I do. Deal?” Silver then upped the ante to $2,000, but drew a rebuke from the public editor of The New York Times, which publishes his blog. “He’s been on a rant, calling me an idiot and a partisan, so I’m asking him to put some integrity behind it,” Silver said in his defense. “I don’t stand to gain anything from it; it’s for charity.”

The payoff: Without accepting the bet, Scarborough pledged $1,000 to the Red Cross on Thursday (and a reader matched his donation). Silver, for his part, tweeted that he donated a brand appropriate $2,538.

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George Clooney vs. Nicole Kidman and Michelle Pfeiffer

George Clooney was so confident he would not get married for a second time that he bet Nicole Kidman and Michelle Pfeiffer $10,000 each that he would still be single and childless at age 40. “If anyone wants to make the same bet for when I’m 50,” he said at the time,” get in touch.”

The payoff: After winning the bet at 40, Clooney returned the money and went double-or-nothing that he would be unmarried and have no children on his 50th birthday. He won again.

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Aaron Rodgers vs. Boyz II Men

Mayors and governors famously make public wagers when their local teams play in a Super Bowl or World Series, but this year a player got in on the action—for a regular-season game.  Green Bay Packers quarterback Aaron Rodgers bet Nathan Morris of Boyz II Men that the Packers would defeat the San Francisco 49ers in the season opener last September. According to TMZ, if the Niners lost, Morris agreed wear a Rodgers jersey all week, and if they won, Rodgers would have to wear the jersey of San Francisco quarterback Alex Smith all week.

The payoff: The 49ers defeated the Packers 30-22, but Rodgers didn’t pay up. “There’s nothing to that,” Rodgers said after the game. “That got blown way out of proportion. It was at best a joke between friends, and, unfortunately, the great reporting of TMZ blew another one.” But Boyz II Men didn’t let him off the hook. They tweeted after the game:“Pressing the jersey now! RT @shawnstockman And that should be that for the Packer/ 9er game. Looks like a jersey will be worn!!”

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Leonardo DiCaprio vs. Tobey Maguire

Would you rather have Jack Dawson as your father or Spider-Man? Best friends Leonardo DiCaprio and Tobey Maguire were so confident that the other would become a father first that the two reportedly bet $25,000 on the prospect.

The payoff: On Nov. 7, 2010, DiCaprio got $25,000 richer when Maguire’s fiancée gave birth to the couple’s daughter, Ruby Sweetheart.

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Bruce Willis vs. Matthew Perry

While filming The Whole Nine Yards in 2000, Matthew Perry was convinced the movie would win the box office in its opening week and so he made a bet with his costar Bruce Willis. If the film was No. 1, Willis, who was scheduled to be a guest star on Friends, would agree to appear for free.

The payoff: The Whole Nine Yards was No. 1 at the box office in its first week and Willis donated his Friends fee to charity. But it worked out OK for Willis—he won an Emmy for Outstanding Guest Actor for his role on Friends.

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Snoop Dogg vs. Donnie Wahlberg

In a classic put-up-or-shut-up bet, Snoop Dogg, a rabid Los Angeles Lakers fan, bet Donnie Wahlberg, a die-hard Boston Celtics fan, on the outcome of the 2010 NBA Finals. The loser would agree to pay $20,000 to the winner’s charity.  Snoop called out the Blue Bloods star in an online video, but that only inspired Wahlberg to up the stakes: The loser also had to appear onstage at a New Kids on the Block reunion concert wearing the winning team’s jersey. (Actor Mike Epps and UFC founder Dana White also got in on the action for the Lakers and Celtics, respectively.)

The payoff: Despite being down 3-2 when the bet was made, the Lakers came back and won the NBA championship in seven games. “Congrats to The Lakers and the Kids in LA who will benefit from my donation!,” Wahlberg tweeted graciously after the loss. [email protected] I got mad love for you for doing this! Congrats!”

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Kelly Ripa vs. Michael Strahan

Does Michael Strahan owe his new job as cohost of Live with Kelly and Michael to a bet he once made? According to Kelly Ripa, he does. “He lost a sports bet and had to babysit for my kids,” Ripa told UsWeekly about the man who succeeded Regis Philbin. “I just looked at him and knew he was a good guy. I said to myself, ‘He would make a great cohost one day.’”

The payoff: After losing to Ripa, the former New York Giants star proved to be a man of his word—and one who is not afraid of cross-dressing. “He had on lipstick and a feather boa while babysitting!” Ripa said of her temporary babysitter. “We like a man that’s willing to dress up like a lady!” And while Strahan was not a sore loser, he did say that Ripa had “sugared [her kids] up,” adding, “They made me do things that I shouldn’t be doing, as a big man.”

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Charles Barkley vs. Kenny Smith

Early in the 2002 NBA season, when Houston Rockets rookie Yao Ming was averaging 3.3 points after his first six games, TNT analyst Charles Barkley made a bold bet with his co-host Kenny Smith: If Yao scored 19 points in any game that season, Barkley agreed to “kiss [Smith’s] ass.”

The payoff: Less than a week after the bet was made, Yao scored 20 points. “If you make a bet, you pay up. Barkley said the next day.” I just told Kenny to take a shower before the show. I made the bet and I’m going to stick by my word. Ugh.” Smith was less-than-thrilled with the victory. “Sometimes even when you win, you lose,” he joked. But Smith had the last laugh. When it came time to pay up, he brought a donkey on the set had Barkley pucker up.

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Warren Beatty vs. Jeffrey Katzenberg

In 1999, Steven Spielberg’s Saving Private Ryan appeared to be a lock to win Best Picture at the Academy Awards, but DreamWorks producer Jeffrey Katzenberg wasn’t convinced. He bet Warren Beatty $10,000 (to the charity of the winner’s choosing) that Miramax would take out more ads for its Oscar contender, Shakespeare in Love.

The payoff: DreamWorks took out 165 ads for Saving Private Ryan, while Miramax only had 118. But it was a double loss for Katzenberg: Not only did Beatty win the bet, but Shakespeare in Love won the Oscar.

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Mitt Romney vs. Rick Perry

During a Republican primary debate in Iowa this year, Texas Governor Rick Perry accused Mitt Romney of altering the paperback version of his book to downplay his pride in his Massachusetts’s health-care plan. Romney denied the allegation, but Perry wasn’t buying it. “I'll tell you what. 10,000 bucks? Ten-thousand-dollar bet?” Romney said, extending his hand.

The payoff: Rick Perry immediately refused to accept the wager, saying, “I’m not in the betting business.” As for Romney, he quickly realized he had made an expensive gaffe. “After the debate was over, Ann came up and gave me a kiss,” Romney told reporters. “She said I did great, but that ‘betting is not one of my strengths.’”