16 years ago director Roger Kumble introduced us to the twisted and revenge-based world of Sebastian Valmont (Ryan Phillippe) and Kathryn Merteuil (Sarah Michelle Gellar) in the film Cruel Intentions.
The movie, which was was based on the 1782 novel Les Liaisons dangereuses, was set among uber-weathy teens attending a New York high school and centered around a bet made between the two step-siblings about whether or not Sebastian could sleep with the virginal headmasters daughter, Annette (Reese Witherspoon). Despite the film creeping up on two decades old, I still maintain that it has one of the best endings of any film with an awesome soundtrack to boot:
But enough of Kathryn's coke necklace and Sebastian's journal, sit back and take a look at what the stellar cast of Cruel Intentions look like after 16 years and a whole lot of revenge:
Sarah Michelle Gellar as Kathryn Merteuil
What you've seen her in since: Buffy the Vampire Slayer (both before and after Cruel Intentions) Angel, Scooby-Doo, The Grudge, The Return, Suburban Girl, Possession, Veronika Decides to Die, Ringer, The Crazy Ones, Robot Chicken,
Fun Fact: In 2008 the kissing scene between Gellar and Selma Blair was voted the 32nd in Entertainment Weekly's "The 50 Sexiest Movies Ever."
Ryan Phillippe as Sebastian Valmont
What you've seen him in since: The Way of the Gun, Antitrust, Gosford Park, Igby Goes Down, Crash, Chaos, Five Fingers, Flags of our Fathers, Breach, The Bang Bang Club, The Lincoln Lawyer, Damages, Straight A's, Secrets and Lies.
Fun Fact: The scene where Sebastian got slapped by Annette was totally real and unscripted! Reese Witherspoon got so into the scene that she unexpectedly slapped Ryan Phillippe and his reaction was so genuine that director Roger Kumble left it in!
Reese Witherspoon as Annette Hargrove
What you've seen her in since: Election, Best Laid Plans, American Psycho, Friends, Little Nicky, Legally Blonde, The Importance of Being Earnest, Sweet Home Alabama, Legally Blonde 2: Red, White and Blonde, Vanity Fair, Walk the Line, Just Like Heaven, Penelope, Rendition, Four Christmases, Water for Elephants, This Means War, Mud, Wild, Inherent Vice, The Good Lie, Hot Pursuit.
Fun Fact: Three months after Cruel Intentions was released Reese Witherspoon and Ryan Phillippe were married. The couple had two children together before divorcing in 2007.
Selma Blair as Cecile Caldwell
What you've seen her in since: Zoe, Duncan, Jack & Jane, Legally Blonde, The Sweetest Thing, A Guy Thing, Hellboy, A Dirty Shame, In Good Company, Lies & Alibis, The Killing Gene, Hellboy II: The Golden Army, Kath & Kim, Web Therapy, Portlandia, The Break In, In Their Skin, Anger Management and she is currently working on American Crime Story.
Fun Fact: Despite playing the young, naive Freshman in the film, Selma Blair is actually five years older than Sarah Michelle Gellar and three years older than Ryan Phillippe.
Joshua Jackson as Blaine Tuttle
What you've seen him in since: The Skulls, Gossip, The Safety of Objects, Dawson's Creek (both before and after Cruel Intentions), Racing Stripes, Shadows in the Sun, Battle in Seattle, Shutter, One Week, Lay the Favorite, Fringe, The Affair.
Fun Fact: Joshua Jackson and Tara Reid (who appeared in the opening scenes of the film as the therapists daughter), also appeared together in the film Urban Legend, which was released the year before Cruel Intentions.
Eric Mabius as Greg McConnell
What you've seen him in since: Tempted, On the Borderline, Resident Evil, The Extreme Team, The Job, The O.C., A Christmas Wedding, Eyes, The L Word, Ugly Betty, Where the Road Meets the Sun, How to Fall in Love, Amazing, Singed, Sealed, Delivered, Chicago Fire.
Fun Fact: The whole film was shot over a six week period, and the initial script was written by director Roger Kumble in just 12 days.
Louise Fletcher as Helen Rosemond
What you've seen her in since: Very Mean Money, Silver Man, Finding Home, Clipping Adam, Aurora Borealis, ER, Fat Rose and Squeaky, The Genesis Code, Cassadaga, Shameless, A Perfect Man.
Fun Fact: The church that Kathryn exits at the end of the film has a plaque to the left of the doorway which says "Rosemond Chapel," the last name of Fletcher's character.
Christine Baranski as Bunny Caldwell
What you've seen her in since: How the Grinch Stole Christmas, Welcome to New York, Citizen Baines, The Guru, Chicago, Marci X, Welcome to Mooseport, Happy Family, Falling for Grace, Relative Strangers, Bonneville, Mamma Mia! Ugly Betty, Into the Woods, The Big Bang Theory and The Good Wife.
Fun Fact: One of the final things that clinched the deal for Christine Baranski to star in the film was the fact that Sarah Michelle Gellar a.k.a. Buffy the Vampire Slayer was in the film, and her daughters were enormous fans.
Complete the full trip down memory lane by taking a listen to the outstanding soundtrack from the film: