Director Begged Reese Witherspoon to Star in Cult Classic 'Cruel Intentions'

Back in 1999, director Roger Kumble was gearing up to make his first feature film, 'Cruel Intentions'. One key role that proved difficult to cast was that of Annette, the story's moral anchor. Kumble had his sights set on actress Vinessa Shaw, but the studio wanted Katie Holmes, who was just starting to gain fame from 'Dawson's Creek'.

Desperate to land his ideal Annette, Kumble turned to the film's leading man, Ryan Phillippe, who was dating Reese Witherspoon at the time. Kumble saw an opportunity and asked Phillippe about his girlfriend. However, Witherspoon was already booked and busy, so it took more than just flattery to convince her.

Kumble and Phillippe decided to take Witherspoon out for dinner in an attempt to win her over. But the plan backfired, as the trio ended up getting drunk. In a last-ditch effort, Kumble literally got down on his knees and begged Witherspoon to take the role, promising it would only be for 15 days. Witherspoon agreed, but with a condition - she wanted to work on the character to make Annette feel more authentic and layered, rather than just a passive presence.

Witherspoon's creative input clearly paid off, as her performance as Annette in 'Cruel Intentions' went on to become an iconic part of the cult classic film.