( The Frisky ) -- Virgin Airlines heir Sam Branson was hanging out with Andy Roddick , and could n't resist challenging him to a bet . Andy Roddick played left-handed against Sam Branson and still won . Branson wagered $ 150 that he could beat Roddick in a tennis match , as long as the right-handed sports star played with his left hand . Even as a leftie , Roddick cleaned up . They played one set and Branson did n't score a single point . Since celebrities have so much money to throw around , they often amuse themselves by placing weird bets . Peep a few more who 've put their money where their mouth is . 1 . George Clooney was so convinced he 'd still be childless and unmarried when he hit 40 that in 2001 , he bet Nicole Kidman and Michelle Pfeiffer $ 10,000 each . The two gals just could n't believe that this hunky dude would n't be tied down . But they were wrong . That 's $ 20,000 for bachelor George ! The Frisky : They dated ? Hollywood 's oddest hookups . 2 . Bruce Willis and Matthew Perry made a bet on the set of `` The Whole Nine Yards . '' Perry allegedly thought the film would open at the top of the charts in the U.S. but Willis was n't feelin ' it . When Bruce lost , he had to do a cameo on `` Friends . '' Does n't sound so bad , right ? Well , he had to give away all the money he made . The good news is , he gave it to charity . The Frisky : Celebs whose new loves look just like their exes . 3 . Tobey Maguire and Leonardo DiCaprio each bet $ 25,000 that the other would become a father first . The Frisky : Hollywood hotties set to play historical figures . When Maguire 's fiance had their first kid , the actor had to pay up . He gave DiCaprio the cash , but did n't mind . Cause , uh , he was a dad . TM & © 2009 TMV , Inc. | All Rights Reserved .
Celebs have so much money they amuse themselves sometimes by placing bets . Sam Branson bet Andy Roddick he could beat him at a tennis match . George Clooney bet two actresses he 'd still be childless at 40 . Bruce Willis lost a bet to Matthew Perry and had to appear on `` Friends ''