One day during the filming of Ocean's Eleven, Matt Damon invited Steven Soderbergh, the film's director, to join him on a trip to a casino to play some Blackjack. Soderbergh declined.
"What's the matter," Damon asked, "Don't you gamble?"
"Of course I do," Soderbergh replied: "I'm gambling with Warner Brother's money right now!"
[It was a well-placed bet: Ocean's Eleven made $450 million and spawned several sequels, which grossed an additional $1 billion.]