Cruel Intentions (1999) – Sarah Michelle Gellar’s Boldest Role That Redefined Teen Cinema
Released in 1999, Cruel Intentions is a seductive teen drama that took Hollywood by storm with its dark themes, bold performances, and provocative storytelling. At the heart of it all was Sarah Michelle Gellar, portraying the cunning and manipulative Kathryn Merteuil—a role that showcased her range far beyond her TV fame in Buffy the Vampire Slayer.
In this blog post, we explore the story behind Cruel Intentions, a detailed analysis of Sarah Michelle Gellar’s performance, key plot moments, the film’s critical reception, and how it became a cult classic among late-90s cinema lovers.
⭐ About the Film: Cruel Intentions Overview
- Release Date: March 5, 1999
- Director: Roger Kumble
- Genre: Teen Drama, Romance, Thriller
- Runtime: 97 minutes
- Main Cast:
- Sarah Michelle Gellar as Kathryn Merteuil
- Ryan Phillippe as Sebastian Valmont
- Reese Witherspoon as Annette Hargrove
- Selma Blair as Cecile Caldwell
🎬 Synopsis:
Cruel Intentions is a modern-day adaptation of the French novel Les Liaisons Dangereuses, set among rich Manhattan teenagers. The story revolves around two step-siblings, Kathryn and Sebastian, who manipulate others as part of a cruel bet—until emotions and consequences complicate their game.
🎭 Sarah Michelle Gellar as Kathryn Merteuil – A Career-Defining Performance
Known widely for her role as Buffy Summers, Sarah Michelle Gellar took a dramatic career turn with Kathryn. The character is a beautiful, sharp-tongued socialite who hides her manipulative and malicious intent behind a mask of charm.
🔥 Why Her Role Stood Out:
- Bold Departure: A far cry from the heroism of Buffy, Gellar’s Kathryn was unapologetically vicious, driven by power and sexual manipulation.
- Memorable Dialogues: Lines like “Everybody loves me, and I intend to keep it that way” made her character unforgettable.
- Fashion & Style: Her look in the film—dark lips, sleek hair, and designer outfits—became a symbol of gothic-chic femme fatale fashion.
Kathryn Merteuil is still considered one of the most iconic female villains in teen film history.
🔍 In-Depth Plot Breakdown (Spoiler Alert!)
Act 1: Setting the Stage
Kathryn and her stepbrother Sebastian are wealthy and bored. Kathryn wants revenge on her ex-boyfriend by corrupting his new innocent girlfriend Cecile. Meanwhile, Sebastian is challenged to seduce the virtuous Annette Hargrove, who publicly advocates for abstinence until marriage.
Act 2: The Games Begin
While Kathryn manipulates Cecile with help from the clueless music teacher, Sebastian begins to genuinely fall for Annette—something that goes against his calculated nature.
Act 3: Real Emotions, Real Consequences
Sebastian ends up in a moral dilemma. After falling in love with Annette, he tries to call off the bet, but Kathryn manipulates him into betraying Annette. In the final twist, Sebastian dies, but not before exposing Kathryn’s lies.
Final Scene: Justice Served
The film ends with Kathryn’s public humiliation at a school memorial where Sebastian’s journal reveals her schemes, turning her into a pariah. Her last scene—tears streaming as her lies are exposed—cemented Sarah Michelle Gellar’s legacy as a master performer.
🏆 Awards & Recognition
While Cruel Intentions didn’t sweep major awards, it achieved cult status, thanks to its cast, writing, and iconic soundtrack.
- Teen Choice Award (1999): Choice Movie: Drama
- MTV Movie & TV Awards:
- Best Kiss (Sarah Michelle Gellar & Selma Blair) – Won
- Best Villain (Sarah Michelle Gellar) – Nominated
🎧 Iconic Soundtrack That Amplified the Mood
The soundtrack of Cruel Intentions played a huge role in the film’s emotional impact.
- “Bittersweet Symphony” – The Verve
- “Colorblind” – Counting Crows
- “Every You and Every Me” – Placebo
The final scene featuring “Bittersweet Symphony” became one of the most memorable in teen drama history.
💬 Cultural Impact & Legacy
- Cult Status: Over time, the film became a cult favorite, especially among millennials who grew up watching it on VHS and late-night TV.
- Pop Culture References: Parodied and referenced in shows like Glee, SNL, and Riverdale.
- Fashion Influence: Kathryn’s dark wardrobe influenced 2000s teen fashion.
- Reboots & Prequels: A 2016 Cruel Intentions TV pilot was made (also starring Gellar), and the film inspired similar stories (Gossip Girl, Pretty Little Liars).
🔥 Sarah Michelle Gellar’s Transformation for the Role
Playing a character as twisted as Kathryn took preparation. Gellar revealed in interviews how she:
- Read Les Liaisons Dangereuses to understand the original character
- Studied classic femme fatales from noir films
- Worked with director Roger Kumble on subtle expressions and cold delivery
This transformation showed her versatility beyond Buffy and horror films (I Know What You Did Last Summer, Scream 2).
👗 Kathryn Merteuil – Fashion Analysis
Kathryn’s style was elegant, powerful, and sultry. She wore:
- Tight-fitting designer dresses
- Dark lipstick and smoky eyes
- Catholic school uniforms with a twist
Her wardrobe was symbolic—sweet on the outside, wicked within.
🌍 Where to Watch Cruel Intentions in 2025
As of 2025, Cruel Intentions is available to stream on:
- Netflix (US/UK/India)
- Amazon Prime Video
- Paramount+
DVDs and Blu-rays still remain popular among fans for the bonus features and director’s commentary.
🙋 FAQs – Cruel Intentions (1999)
❓ What is Cruel Intentions about?
Cruel Intentions is a teen drama that follows two manipulative step-siblings who use seduction and lies to control those around them.
❓ Who plays Kathryn in Cruel Intentions?
Sarah Michelle Gellar plays the manipulative Kathryn Merteuil in the movie.
❓ Is Cruel Intentions based on a book?
Yes, it is based on the French novel Les Liaisons Dangereuses by Pierre Choderlos de Laclos.
❓ Is Cruel Intentions a true story?
No, the story is fictional and based on a classic French novel.
❓ Was there a sequel to Cruel Intentions?
There were direct-to-video prequels and sequels, but none reached the original’s success. A TV series was planned in 2016 but not picked up.
💡 Final Thoughts
Cruel Intentions is more than just a 90s teen drama—it’s a layered film with bold themes, unforgettable performances, and an iconic portrayal of villainy by Sarah Michelle Gellar. Her role as Kathryn Merteuil remains one of the most daring and captivating female roles in teen cinema history.
If you haven’t seen it—or haven’t seen it recently—it’s time to experience (or re-experience) the twisted brilliance of Cruel Intentions.