The studio wanted Katie Holmes, the star of Dawson’s Creek. But scriptwriter Roger Kumble decided that he needed someone with a stronger personality. He saw Ryan Phillippe’s girlfriend once (Reese Witherspoon) and asked him to invite her for dinner.

At the dinner, Roger literally kneeled down before the young actress. He remembers saying, “Please, it’ll be 15 days, you’ll be great.” And Reese was like, “I’ll do it. But we need to work on the character.” Roger was like, “Anything, anything, anything. She wanted to strengthen the character, and she was right. And she and I got together, and we gave Annette more bite, so she wasn’t a doormat. And I’m very grateful to her for that.”