Looking back at "Cruel Intentions," it’s hard to imagine anyone other than Reese Witherspoon playing the female lead Annette.
But as most big movies go, another big-time actress was originally up for the role: Katie Holmes.
"We got into disagreements over who was going to play Annette," Kumble told Cosmo. "The studio wanted Katie Holmes, who was just starting to do 'Dawson's Creek.' And I liked this actor Vinessa Shaw. And they were both great."
He continued, "But this was early Katie, and I thought we needed someone with a little more strength of character. And we just couldn't agree. And then, literally, I was hanging out with Ryan one night and I was like, 'What about your girlfriend?'"
Phillippe, 39, was already dating Witherspoon and the director revealed that the idea was to take her out, get her drunk, so she would say "yes" to the role.
"So, basically, we took Reese out to dinner to get her drunk, and we ended up getting drunk," he said. “And I literally got down on my knees and begged her: '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.' I'm 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."
He also opened up about a problem Phillippe had shooting the breakup scene with his then-girlfriend Witherspoon, 38.
"He threw up on set," Kumble said. "And it was one of those things where I just let the cameras roll. 'Let's go back, do it again, let's go back.' I want to be professional, but until I feel like we have it, you just have to go.
“As a director, you're like, 'I'm not going to be the most liked person today.' I don't think we did too many takes. But, you know, you get what you need to get. You really want to see him ripping his heart out."
And that final scene with "Bittersweet Symphony" playing in the background, Kumble said they almost had to use another song!
"That was another example of me writing a scene perfectly to music without getting the rights. That was a nightmare. It just fit amazingly [in the final scene] — the strings hitting as she's breaking down on the podium and then you cut outside right when the song kind of kicks in and it just accomplished everything," he said. "So we're like, 'Oh, let's get the rights from The Verve.'
“But then you find out The Verve doesn't own the rights, The Rolling Stones own the rights. So it was a headache. It was one of those things where the studio was like, 'Try another song.' And we kept trying and trying and no one could agree. And the studio was like, 'Let's just pay for it.' We paid for everything, but we really paid for that one."