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Reese Witherspoon Shares Cruel Intentions Throwback Thursday With Ex-Husband Ryan Phillippe, Sarah Michelle Gellar

Throwing it back! Reese Witherspoon‘s #TBT from Thursday, Sept. 18, was an amazing reminder of the Oscar winner’s early years in Hollywood. See pics of Reese’s best Hollywood moments.

“Ahh the 90’s…” Witherspoon, 38, wrote alongside a snap from the set of her 1999 flick, Cruel Intentions, featuring the film’s central characters: Witherspoon, her then-boyfriend (and later first husband) Ryan Phillippe, and Sarah Michelle Gellar.

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Screenwriter/director Roger Kumble revealed last month that he “begged” Witherspoon to play Annette Hargrove in the drama. “We got into disagreements over who was going to play Annette,” Kumble told Cosmopolitan. “The studio wanted Katie Holmes, who was just starting to do Dawson’s Creek. And I liked this actor Vinessa Shaw… And then, literally, I was hanging out with Ryan one night and I was like, ‘What about your girlfriend?'”

reese witherspoon and ryan Phillippe in cruel intentions
“We ended up getting drunk and I literally got down on my knees and begged her,” Cruel Intentions director Roger Kumble said of Reese Witherspoon.

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He and Phillippe used some sneaky tactics to get Witherspoon on board — which later backfired. “So, basically, we took Reese out to dinner to get her drunk,” Kumble said. “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.'”

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Even in her early 20s, the Walk the Line actress knew how she wanted to develop the virtuous Annette to her own liking. “Reese was like, ‘I’ll do it. But we need to work on the character,'” Kumble recalled. “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.”

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Witherspoon and Phillippe were among young Hollywood’s hottest couples when they filmed the smash drama. In June 1999, Three months after Cruel Intentions was released, the couple married; Witherspoon was six-months pregnant with their first child Ava at the time. In honor of their daughter’s 15th birthday this month, Phillippe got nostalgic and recalled a sweet moment with Reese from Ava’s birth.

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“With my stomach in knots, exhausted & dirty, covered in syrupy fake blood & shards of candy glass the heli[copter] found the pad and I was taken to an area to sterilize myself,” Phillippe revealed via Twitter on Tuesday, Sept. 9. “I made it to my then wife’s bedside w/ two hours to spare before my baby girl first entered the world. 15 years ago I learned what love truly is.”

The exes, also parents to 10-year-old son Deacon, split in 2006 and finalized their divorce in 2008.

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