For immoderate reason, the film's archetypal rubric was Cruel Inventions, arsenic revealed by Gellar connected Instagram in a Throwback Thursday post. 

"#throwbackthursday ok 1 past 1 due to the fact that I was feeling nostalgic - and yes #CruelInventions was the archetypal title," she wrote. "This pic was 1998 astatine our footwear disconnected dinner #cruelintentions #Crueltv#kathrynmerteuil."

And portion the movie was intelligibly a modern retelling of Les Liaisons dangereuses, Kumble besides drew inspiration from another source.

"There was this movie called Welcome to the Dollhouse that Todd Solondz did," he told the Telegraph. "I loved that movie and I loved the information that helium was capturing mean teenagers, and I'd ne'er seen it done that way."

Part of the crushed Phillippe and Gellar ended up snagging their roles successful Cruel Intentions was due to the fact that of their enactment successful the 1997 fearfulness hit I Know What You Did Last Summer thanks to the 2 film's making the aforesaid producer, Neal Moritz.

"He was like, 'I conscionable made this movie, I Know What You Did Last Summer, and determination are these 2 actors successful it; you truly should conscionable them.' And it was Ryan Phillippe and Sarah Michelle Gellar," Kumble revealed to Cosmo. "And they were great. And I was conscionable excited to get my movie made, truthful I was like, 'Great!' Once we formed Sarah and Ryan, past it got heat; we had 2 blistery actors."

One of Hollywood's hottest blondes acknowledgment to her star-making crook on Buffy the Vampire Slayer, Gellar wanted to abstracted herself from the fashionable WB bid erstwhile it came to the seductive and devious Kathryn. 

"That was Sarah's thing: 'I don't privation to look similar Buffy'" Kumble recalled. 

But it was much than conscionable the hairsbreadth alteration that helped Gellar, who grew up connected the Upper East Side herself, present specified a stellar performance, arsenic she truly was capable to clasp the debauchery of the quality without wanting to marque her sympathetic. 

"We had agelong talks astir her history. Roger utilized to ever say, ‘Don't you deliberation that she was abused?'" she told Premiere mag successful 1999. "And I'd say, 'No, I deliberation she had a cleanable upbringing. I deliberation her parent adored her and her begetter sent her astonishing gifts. She conscionable wanted more."

Looking backmost connected the experience, Gellar revealed to The Huffington Post that Cruel Intentions was 1 of her 2 "best movie experiences," explaining, "We conscionable knew we were making thing that was truthful antithetic and we were each truthful passionate and truthful excited. And we were each friends! It was conscionable specified a large clip making that and letting it spell arsenic acold arsenic it did."

There was 1 facet of playing the "Marcia f--king Brady of the Upper East Side" that Gellar did not love: "Although, the ground-up chamomile, the substitute I utilized for coke was not fun. I person allergies and since chamomile is benignant of pollen-like, my chemoreceptor and pharynx had it unsmooth for a while."

Before casting Phillippe successful the role, Kumble had his oculus connected different up and coming young actor.

"I was besides looking at Jonathan Rhys Meyers at the time, due to the fact that a batch of young Hollywood backmost past wanted to bash it," helium told The Telegraph. "Ryan conscionable had that benignant of Valmont aerial astir him."

The Irish histrion would spell connected to prima successful Bend It Like Beckham, Match Point and Mission: Impossible III, arsenic good arsenic yet co-star other Witherspoon successful Vanity Fair. 

While Witherspoon snagged the relation of bully miss Annette, TV's favourite miss adjacent doorway Katie Holmes was up for the part.

"This was aboriginal Katie, and I thought we needed idiosyncratic with a small much spot of character," Kumble said of yet passing connected the Dawson's Creek star.

Another sanction up for the portion was Hocus Pocus' Vinessa Shaw, but the workplace reportedly said no.

And then, of course, helium wanted Witherspoon, going done her then-boyfriend Phillippe to snag her. "Literally, I was hanging retired with Ryan 1 nighttime and I was like, 'What astir your girlfriend?'"

Kumble and Phillippe teamed up to person Witherspoon, past 22 and known for her enactment successful Fear and Pleasantville, to play Annette.

"So, basically, we took Reese retired to meal to get her drunk, and we ended up getting drunk. And I virtually got down connected my knees and begged her: 'Please, it'll beryllium 15 days, you'll beryllium great,'" Kumble recalled to Cosmo. "And Reese was like, 'I'll bash it. But we request to enactment connected the character.'"

And adjacent backmost past Witherspoon, who has go 1 of Hollywood's astir vocal supporters of Time's Up, was each astir pistillate empowerment. 

"She wanted to fortify the character, and she was right," Kumble said. "And she and I got together, and we gave Annette much wound truthful she wasn't a doormat. And I'm precise grateful to her for that."

Witherspoon wasn't the lone idiosyncratic that had to beryllium talked into signing connected to Cruel Intentions, arsenic The Good Fight's Christine Baranski revealed she initially wanted to walk connected the relation of Cecile's uptight mother, Bunny Caldwell. Once again, Kumble resorted to begging. 

"I had to beryllium talked into doing that one," she admitted to the LA Times. "It was going to beryllium changeable during my archetypal year's hiatus from Cybill and I was anxious to spell location and beryllium with my kids. The manager begged and begged maine and said, 'It's lone a fewer scenes.'

It ended up paying off, arsenic she continued, "I'm inactive making residual wealth disconnected Cruel Intentions. It mightiness beryllium the movie that's made maine the astir successful residuals due to the fact that it is specified a hit. I didn't bash overmuch successful that movie and yet radical volition travel up to maine and punctuation my lines."

Back successful 1999, Gellar and Blair's onscreen buss was a large deal. And it won the grant for Best Kiss astatine the 2000 MTV Movie Awards, with the pals recreating the buss connected stage.

Not successful the script? That iconic drawstring of spit that follows their kissing lesson. "I hide who, but idiosyncratic said, 'We request to spell again, there's saliva connecting them.' And [cinematographer] Theo [van de Sande] was like, 'No, it's beautiful.' And I was like, 'No, it's hot. I mean, we'll spell again, but I deliberation it's cool,'" Kumble recalled to Cosmo. "So it was a blessed accident. And it's benignant of been remembered for that."

When it came to really filming it, Gellar erstwhile said, "Selma was acrophobic she would suck astatine kissing me. But she didn't!"

Blair (who was really 27 playing the 15-year-old freshman Cecile) admitted to immoderate archetypal nerves, but revealed Gellar had immoderate too, saying, "Besides kissing my sister years agone successful a crippled of information oregon dare, I had ne'er kissed a miss up to the constituent wherever I had to buss Sarah. We changeable our kissing country connected the past time of filming. And, it really felt great. On our mode from LA to NYC to movie the country successful Central Park, I said to Sarah, 'Tomorrow we get to marque out!' She was like, 'Shhhh. Don't speak.'"

For Gellar, the kiss, which was performed successful Central Park with hundreds of extras and photographers around, ended up making tabloid headlines the pursuing week. "[We] saw headlines that said thing like, 'Sarah spends a time successful Central Park with a friend,'" Blair remembered. "I conjecture they each had their telescopic lenses acceptable that day."

How did Blair extremity up landing the relation that would service arsenic her large break? By being conscionable arsenic bratty arsenic her character. 

"It was the smartest audition I've ever seen successful my career. I retrieve Selma came successful and I said, 'How aged are you?' And she goes [in Cecile's bratty voice] 'How aged are you?'" Kumble told Cosmo. "And she was truthful obnoxious and I couldn't get it retired of my head. She came into the audition arsenic the quality and didn't amusement maine that determination was Selma; I said, 'This is the person.'"

Another tiny relation that was filled by idiosyncratic who would spell connected to predominate headlines? Eventual prima of The Bachelor Charlie O'Connell, Jerry O'Connell's younger brother, who plays Kathryn's boyfiend, Court Reynolds.

And amusive fact: Before she began dating her eventual hubby Freddie Prinze Jr., Gellar and Jerry O'Connell really were a couple. They met connected the acceptable of Scream 2 prior to Cruel Intentions. "We did day afterwards," Jerry revealed to People. "Not during shooting. We would've ne'er analyzable enactment and pleasance relationships." 

A superior mates successful real-life, Phillippe and Witherspoon had a pugnacious clip shooting Sebastian and Annette's break-up. In fact, it felt truthful aggravated for the mates that Phillippe physically got sick. 

"Reese and I had a combat country wherever we had to accidental horrible things to each different for 4 consecutive hours. After it was each over, I went extracurricular and virtually threw up," Phillippe told The Morning Call. "It was truthful emotionally punishing for me."

But wasn't the lone 1 struggling with the scene, arsenic the infamous slap Annette delivered crossed Sebastian's look was unplanned. 

"At 1 constituent I was improvising off-camera for Reese," helium recalled, "I conjecture I said immoderate beauteous mean things, truthful she came implicit and slapped me. Roger loved it truthful overmuch helium incorporated it into the scene. So fundamentally I got slapped astir for a mates of hours."

Though astir radical deliberation the erstwhile mates met connected the acceptable of Cruel Intentions, Phillippe and Witherspoon actually met erstwhile helium crashed her 21st day enactment years prior.

"It was a beauteous intense, affectional transportation that happened betwixt Reese and me," helium said. "There's a definite equilibrium there. Reese is simply a happy, light-hearted person, but she's besides incredibly intelligent. I thin to beryllium considerably darker. She keeps maine from getting excessively acheronian and depressed and that's indispensable successful a concern that's based connected uncertainty and insecurity."

Go backmost and ticker the movie and you'll spot the costume decorator dressed each quality with care. Annette's all-light wardrobe was expected to beryllium successful stark opposition to Sebastian's all-black look. 

"Her palette was softer and sweeter but confident," Denise Wingate told Dazed. "I retrieve we wanted her successful each achromatic successful opposition to Ryan's each black, and erstwhile helium gets deed by a car and sees her it's astir arsenic if she is an angel."

As for Cecile, it was each UES prim and due but from 1 cardinal portion that served arsenic a acheronian homage to a fairy tale.

"I retrieve astatine the past infinitesimal deciding to enactment Selma successful a reddish hooded sweatshirt truthful erstwhile she is leaving to spell spot Sebastian she looked similar a modern Little Red Riding Hood going to spot the Big Bad Wolf," Wingate recalled. "A batch of subliminal things spell into my enactment of costumes that usually cipher notices."

Spoiler alert: Sebastian inactive dies! Just successful a somewhat antithetic way. 

In an alternate mentation of the film's melodramatic ending, Sebastian is inactive deed by a car, but not due to the fact that helium is protecting Annette from being hit. Instead, helium conscionable stops warring Ronald (Sean Patrick Thomas) erstwhile helium sees her approaching and gets unexpectedly deed by a conveyance erstwhile going to transverse the thoroughfare to speech to her.

The highest paid idiosyncratic connected the film? The Rolling Stones. Why? As it turns retired The Verve's "Bittersweet Symphony," which is everlastingly tied to Cruel Intentions, wasn't actually the band's to merchandise the rights to. 

"That was different illustration of maine penning a country perfectly to euphony without getting the rights," Kumble told ABC News. "That was a nightmare… So we're like, 'Oh, let's get the rights from The Verve.' But past you find retired The Verve doesn't ain the rights, The Rolling Stones ain the rights."

"So it was a headache," helium continued. "It was 1 of those things wherever the workplace was like, 'Try different song.' And we kept trying and trying and nary 1 could agree," helium continued. "And the workplace was like, 'Let's conscionable wage for it.' We paid for everything, but we really paid for that one."

Fortunately, it was wealth good spent. 

One of the astir iconic offerings from the '90s soundtrack the movie boasted had to be The Counting Crows' "Colorblind," which is the opus Sebastian and Annette's emotion country is acceptable to. 

However, the filmmakers initially had a wholly antithetic opus successful place. 

"For that scene, determination was this Smashing Pumpkins opus called 'To Sheila,' which acceptable perfectly. If you crook disconnected the Counting Crows and play the country to 'To Sheila,' it really works rather nicely. And [it seemed like] we were getting the song, it was great," Kumble told Cosmo. "Billy Corgan was watching the movie. It was down to the wire, and past they springiness maine the call: 'Smashing Pumpkins said no.' And we were like, 'Oh, f--k.' Because we were each successful statement then—the producers, the studio, and I: This is the close song."

While determination was a statement implicit which opus to pick...until The Counting Crows' pb vocalist Adam Duritz saw the movie and inspiration instantly struck. 

"The euphony supervisor came successful and said, 'Adam Duritz saw the movie and loved it and helium wrote this opus and they're signaling it contiguous oregon time night, but here's a demo of it.' And we heard the opening, the piano, and we were like, 'Oh my god, this is great. We emotion this,'" Kumble said. "And Neal and I, we went to Adam's house, oregon the Crows' location they were renting astatine the time...and watched them grounds 'Colorblind.' We enactment it connected the movie and it was great."

Once 1 of young Hollywood's hottest couples, Phillippe and Witherspoon went their abstracted ways successful 2007 aft 8 years of marriage. 

Looking backmost connected their split, Phillippe took the blame, saying, "I deliberation much of the occupation was age. When we got unneurotic we were truthful young I deliberation it tin make issues with 2 radical successful this manufacture due to the fact that there's truthful overmuch sound that goes on with it."

After welcoming their girl Ava successful 1999, 3 months aft getting married, and lad Deacon successful 2003, Witherspoon said she "would ne'er alteration anything," but talked astir settling down astatine specified a young property successful a 2017 ITV interview.

"I got joined erstwhile I was 23 and I had 2 kids by the clip I was 27. So I don't know, you know, sometimes it's bully to cognize yourself," the Big Little Lies prima shared. "I would ne'er alteration anything. I've said to my daughter, I think, you know, [at] 25, you commencement to cognize yourself a small spot better."

In 2011, the Oscar victor joined Hollywood powerfulness cause Jim Toth, and person 10-year-old son, Tennessee, together.