Although George Clooney seems to have it all (good looks, money, a successful acting career, and success with the ladies), he does seem to have one flaw: the man can’t gamble. One of his best friends, Matt Damon, claims the following: “George is a loser. We were in Vegas and he was like, ‘I have never won anything in my life gambling.’ I said, ‘I know how to play. I’ll show you. Don’t worry about it.’ Then, he lost 25 straight blackjack hands in a row, which I think is a record. I would never have believed it unless I saw it happen. Afterwards, he slipped a cheque under my hotel room door for $2,500 that said, ‘For services rendered,’ but it wasn’t signed, so I couldn’t cash it.”
Clooney and Damon worked together on the 2001 casino themed movie “Ocean’s Eleven” and seem to have been friends ever since.
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