Columbia Pictures wanted Katie Holmes to play Annette Hargrove, but writer and director Roger Kumble didn't think she had enough strength of character for the role. Ryan Phillippe was already signed on as Sebastian Valmont when Kumble asked about his girlfriend, Reese Witherspoon. "So, basically, we took Reese out to dinner to get her drunk, and we ended up getting drunk," Kumble revealed in 2014. "And I literally got down on my knees and begged her: 'Please, it'll be fifteen days, you'll be great.'" Witherspoon agreed.

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