That spit kiss and vomiting on set: 9 things you didn’t know about Cruel Intentions.

As we reminisce all things Cruel Intentions on its 25th anniversary, here are nine things you didn’t know about the iconic movie.

Katie Holmes was originally up for the role of Annette.

While searching for the perfect fit for the sweet and innocent Annette, producers were drawn to Katie Holmes, who was appearing as Joey on Dawson’s Creek¬†at the time.

But while the studio were keen to cast Holmes for the role, director Roger Kumble wanted Hocus Pocus‘ Vinessa Shaw instead.

After both sides came to a stalemate, Kumble was drawn to the idea of using Ryan Phillippe’s girlfriend, Reese Witherspoon.

While Witherspoon initially turned down the role, she eventually changed her mind.

Watch the trailer for Cruel Intentions below. Post continues after video.

Video via Columbia Pictures.

“So, basically, we took Reese out to dinner to get her drunk, and we ended up getting drunk. And I literally got down on my knees and begged her: ‘Please, it’ll be 15 days, you’ll be great,'” Kumble told Cosmopolitan.¬†