''Cruel Intentions'' is a 1999 American
teen romantic drama
Drama is the specific Mode (literature), mode of fiction Mimesis, represented in performance: a Play (theatre), play, opera, mime, ballet, etc., performed in a theatre, or on Radio drama, radio or television.Elam (1980, 98). Considered as a g ...
film written and directed by
Roger Kumble, and starring
Ryan Phillippe
Matthew Ryan Phillippe ( ; born September 10, 1974) is an American actor. After appearing as Billy Douglas (One Life to Live), Billy Douglas on the soap opera ''One Life to Live'' (1992–1993) and making his feature film debut in ''Crimson Tide ...
,
Sarah Michelle Gellar,
Reese Witherspoon
Laura Jeanne Reese Witherspoon (born March 22, 1976) is an American actress and producer. She is the recipient of List of awards and nominations received by Reese Witherspoon, various accolades, including an Academy Award, a Primetime Emmy Aw ...
, and
Selma Blair. The film, set in New York City among rich high schoolers, is a modern retelling of
Pierre Choderlos de Laclos
Pierre Ambroise François Choderlos de Laclos (; 18 October 1741 – 5 September 1803) was a French novelist, official, Freemason and army general, best known for writing the epistolary novel '' Les Liaisons dangereuses'' (''Dangerous Liaisons ...
' 1782 novel ''
Les Liaisons dangereuses
''Les Liaisons dangereuses'' (; English: ''Dangerous Liaisons'') is a French epistolary novel by Pierre Choderlos de Laclos, first published in four volumes by Durand Neveu on March 23, 1782.
It is the story of the Marquise Isabelle de Merteu ...
''.
Initially a smaller-budget
independent film
An independent film, independent movie, indie film, or indie movie is a feature film or short film that is film production, produced outside the Major film studios, major film studio system in addition to being produced and distributed by independ ...
, it was picked up by
Columbia Pictures
Columbia Pictures Industries, Inc., Trade name, doing business as Columbia Pictures, is an American film Production company, production and Film distributor, distribution company that is the flagship unit of the Sony Pictures Motion Picture Group ...
and widely released on March 5, 1999. Despite mixed critical reviews, the performances of Gellar, Philippe, and Witherspoon were praised and the film grossed $76 million worldwide. Since its release, the film has become regarded as a
cult classic
A cult following is a group of Fan (person), fans who are highly dedicated to a person, idea, object, movement, or work, often an artist, in particular a performing artist, or an artwork in some List of art media, medium. The latter is often cal ...
.
Its box office success spawned a
media franchise
A media franchise, also known as a multimedia franchise, is a collection of related media in which several derivative works have been produced from an original creative work of fiction, such as a film, a work of literature, a television program, o ...
with a
prequel in 2000 and a
sequel in 2004, as well as a
jukebox musical in 2015 and a
2024 television series.
Plot
In New York City, wealthy teenager Sebastian Valmont regularly manipulates and seduces women, but seeks someone who poses a challenge to his charm. He settles on Annette Hargrove—the daughter of his new school headmaster—who is staunchly opposed to sex before falling in love. Sebastian and his equally manipulative stepsister, the intelligent and popular
Kathryn Merteuil, agree to a bet: if Sebastian fails to seduce Annette, then Kathryn gets his vintage
Jaguar XK140
The Jaguar XK140 is a sports car manufactured by Jaguar Cars, Jaguar between 1954 and 1957 as the successor to the Jaguar XK120, XK120. Upgrades included more interior space, improved brakes, rack and pinion steering, increased suspension trav ...
; if he wins, Kathryn will finally have sex with him. Kathryn tries to recruit Sebastian into her own scheme to take revenge on her ex-boyfriend Court Reynolds, who left her because of her promiscuity and began dating the naive and innocent Cecile Caldwell.
Sebastian's initial efforts to seduce Annette fail as she has been informed of his reputation. He suspects Annette's friend Greg, a closeted homosexual, of being responsible and blackmails him into convincing Annette of his good nature. Sebastian also learns that Cecile's mother warned Annette and agrees to corrupt Cecile as revenge. Kathryn notices romantic tension between Cecile and her young music teacher Ronald Clifford and reveals this to Cecile's mother, who fires Ronald. Sebastian and Kathryn convince Ronald to fight for Cecile by writing her a love letter which Sebastian uses to lure Cecile to his bedroom, where he blackmails her into receiving oral sex from him. The next day, Kathryn advises Cecile to have sex with Sebastian and be as promiscuous as possible so she can please Ronald.
Spending time with Annette, Sebastian develops genuine feelings for her, attracted to her honesty and ability to make the normally stoic Sebastian laugh. He kisses Annette but she resists because she also has feelings for him and fears she cannot restrain herself around him. Sebastian calls her a hypocrite for rejecting the opportunity for true love and she finally relents and begins undressing, but Sebastian, confused about his own feelings, declines to have sex with her. Annette leaves the following day, but Sebastian finds her, professes his feelings, and they have sex.
A jealous Kathryn tries to seduce Sebastian but is frustrated that her hold over him has been broken by his feelings for Annette, and she convinces him that he cannot change his true nature. Sebastian plans to tell Annette the truth about the bet but Kathryn warns him that he will only destroy both his and Annette's reputations. He devastates Annette by lying that he only wanted her for sex and feels nothing for her. Sebastian tells Kathryn that he has broken up with Annette, and, having won the bet, wants his reward, but she dismisses him. Kathryn reveals that he was the true target of her scheme and that she manipulated him into feeling shame over his love for Annette for her own amusement.
Sebastian tries to contact Annette to confess the truth and beg for a second chance, but she refuses to see him. He gives her his journal, in which he has detailed Kathryn's manipulative schemes, their bet, and his true feelings for Annette. Seeking revenge, Kathryn calls Ronald, claiming that Sebastian hurt her and slept with Cecile. Ronald violently confronts Sebastian, and the ensuing fight migrates to the middle of the street. Annette tries to intervene but is thrown into traffic and Sebastian is fatally wounded pushing her to safety. Sebastian and Annette confess their love for each other before he dies.
At Sebastian's funeral, Kathryn, unmoved by Sebastian's death, begins to deliver a eulogy, but people leave before she can finish. Kathryn rushes outside to find Cecile handing out copies of Sebastian's journal, titled ''Cruel Intentions''. As the details of her manipulations, promiscuity, and drug abuse are made public, Kathryn weeps as her reputation and good-girl persona are destroyed. Annette drives down a highway in Sebastian's car while wearing his sunglasses and with his journal at her side, recalling their fondest moments together.
Cast
*
Sarah Michelle Gellar as
Kathryn Merteuil, based on the Marquise de Merteuil
*
Ryan Phillippe
Matthew Ryan Phillippe ( ; born September 10, 1974) is an American actor. After appearing as Billy Douglas (One Life to Live), Billy Douglas on the soap opera ''One Life to Live'' (1992–1993) and making his feature film debut in ''Crimson Tide ...
as Sebastian Valmont, based on the Vicomte de Valmont
*
Reese Witherspoon
Laura Jeanne Reese Witherspoon (born March 22, 1976) is an American actress and producer. She is the recipient of List of awards and nominations received by Reese Witherspoon, various accolades, including an Academy Award, a Primetime Emmy Aw ...
as Annette Hargrove, based on Madame de Tourvel
*
Selma Blair as Cecile Caldwell, based on Cécile Volanges
*
Louise Fletcher
Estelle Louise Fletcher (July 22, 1934 – September 23, 2022) was an American actress. She is perhaps best known for her portrayal of the antagonist Nurse Ratched in the film '' One Flew Over the Cuckoo's Nest'' (1975), which earned her numero ...
as Helen Rosemond, based on Madame de Rosemonde
*
Joshua Jackson as Blaine Tuttle
*
Eric Mabius as Greg McConnell
*
Sean Patrick Thomas as Ronald Clifford, based on the Chevalier Danceny
*
Swoosie Kurtz
Swoosie Kurtz ( ; born September 6, 1944) is an American actress. She is the recipient of an Emmy Award and two Tony Awards.
Kurtz made her Broadway debut in the 1975 revival of '' Ah, Wilderness''. She has received five Tony Award nomination ...
as Dr. Regina Greenbaum (Kurtz portrayed Madame de Volanges in the 1988 film version of ''
Dangerous Liaisons'')
*
Christine Baranski as Bunny Caldwell, based on Madame de Volanges
*
Alaina Reed Hall as Nurse
*
Hiep Thi Le as Mai-Lee
*
Deborah Offner as Mrs. Michalak
*
Tara Reid
Tara Donna Reid (; born November 8, 1975) is an American actress and model. Her film roles established her status as a sex symbol in the late 1990s through the early 2000s.
In film, Reid is best known for her lead ensemble role as Vicky Lathum ...
as Marci Greenbaum
*
Drew Snyder
Drew Snyder (born September 25, 1946 in Buffalo, New York) is an American actor of film and television. He is best known for his roles in films such as '' Commando, Firestarter,'' and '' Cruel Intentions'', a well as numerous guest and recurring ...
as Headmaster Hargrove
*
Herta Ware as Mrs. Sugarman
*
Charlie O'Connell as Court Reynolds, based on the Comte de Gercourt
*
Fred Norris as Meter Maid
Production

One of the filming locations was
Old Westbury Gardens in
Nassau County, New York, as well as the
Harry F. Sinclair House
The Harry F. Sinclair House is a mansion at the southeast corner of 79th Street (Manhattan), East 79th Street and Fifth Avenue on the Upper East Side of Manhattan in New York City, New York, U.S. The house was built between 1897 and 1899. Over ...
in New York City. In a 2016 interview, Sarah Michelle Gellar revealed that the original title of the movie was "Cruel Inventions".
Reception
On
Rotten Tomatoes
Rotten Tomatoes is an American review aggregator, review-aggregation website for film and television. The company was launched in August 1998 by three undergraduate students at the University of California, Berkeley: Senh Duong, Patrick Y. Lee ...
, ''Cruel Intentions'' has an approval score of 54% based on 119 reviews, with an average rating of 5.20/10. The site's critics consensus states: "This darkly comic drama and its attractive young cast are easy on the eyes, but uneven performances and an uninspired script conspire to foil ''Cruel Intentions''."
Metacritic
Metacritic is an American website that aggregates reviews of films, television shows, music albums, video games, and formerly books. For each product, the scores from each review are averaged (a weighted average). Metacritic was created ...
gave the film a weighted average score of 56 out of 100 based on 24 critics, indicating "mixed or average" reviews. Audiences polled by
CinemaScore
CinemaScore is an American market research firm based in Las Vegas. It surveys film audiences to rate their viewing experiences with letter grades, reports the results, and forecasts box office receipts from the data.
Background
Ed Mintz, who ...
gave the film an average grade of "B-" on an A+ to F scale.
Charles Taylor of ''
Salon.com'' described the film as "the dirtiest-minded American movie in recent memory – and an honestly corrupt entertaining picture is never anything to sneeze at".
Stephen Holden
Stephen Holden (born July 18, 1941) is an American writer, poet, and music and film critic.
Biography
Holden earned a Bachelor of Arts degree in English from Yale University in 1963. He worked as a photo editor, staff writer, and eventually be ...
of ''
The New York Times
''The New York Times'' (''NYT'') is an American daily newspaper based in New York City. ''The New York Times'' covers domestic, national, and international news, and publishes opinion pieces, investigative reports, and reviews. As one of ...
'' wrote: "You have the queasy sense that the whole thing is just an elaborate stunt and, in this case, an exploitative one."
Roger Ebert
Roger Joseph Ebert ( ; June 18, 1942 – April 4, 2013) was an American Film criticism, film critic, film historian, journalist, essayist, screenwriter and author. He wrote for the ''Chicago Sun-Times'' from 1967 until his death in 2013. Eber ...
of ''
The Chicago Sun-Times
The ''Chicago Sun-Times'' is a daily Non-profit journalism, nonprofit newspaper published in Chicago, Illinois, United States. Since 2022, it is the flagship paper of Chicago Public Media, and has long held the second largest circulation am ...
'' praised ''Cruel Intentions'' and gave the film three out of four stars in his review, stating that it was "smart and merciless in the tradition of the original story".
Box office
''Cruel Intentions'' was a commercial success, grossing $13,020,565 in its opening weekend, ranking No. 2 behind ''
Analyze This''; released in 2,312 theaters, the movie raked in $76.3 worldwide against a $10.5 million budget.
Awards and nominations
Soundtrack
The ''Cruel Intentions'' soundtrack is a compilation soundtrack released on March 9, 1999, by
Arista/
Virgin Records
Virgin Records is a British record label owned by Universal Music Group. They were originally founded as a British independent record label in 1972 by entrepreneurs Richard Branson, Simon Draper, Nik Powell, and musician Tom Newman (musician), ...
. It reached number 60 on the Billboard chart. The lead track for the film was "
Bitter Sweet Symphony
"Bitter Sweet Symphony" is a song by the English rock band the Verve, released on 16 June 1997 by Hut Recordings and Virgin Records as the lead single from their third album, ''Urban Hymns''. It was produced by Youth (musician), Youth at Olympi ...
" by rock band
The Verve
The Verve were an English Rock music, rock band formed in Wigan in 1990 by lead vocalist Richard Ashcroft, guitarist Nick McCabe, bass guitarist Simon Jones (musician), Simon Jones and drummer Peter Salisbury. Guitarist and keyboard player Sim ...
.
Subsequent media
Direct-to-video films
''
Cruel Intentions 2'' was released
direct-to-video
Direct-to-video or straight-to-video refers to the release of a film, television series, short or special to the public immediately on home video formats rather than an initial theatrical release or television premiere. This distribution strat ...
in 2001, written and directed by
Roger Kumble, assembled from three episodes filmed for ''Manchester Prep'', a
prequel
A prequel is a literary, dramatic or cinematic work whose story precedes that of a previous work, by focusing on events that occur before the original narrative. A prequel is a work that forms part of a backstory to the preceding work.
The term ...
series scrapped by
Fox. The story features younger versions of Sebastian Valmont and
Kathryn Merteuil played by
Robin Dunne and
Amy Adams
Amy Lou Adams (born August 20, 1974) is an American actress. Known for both her comedic and dramatic roles, she has been featured three times in annual rankings of the world's highest-paid actresses. She has received List of awards and nom ...
, respectively.
''
Cruel Intentions 3'' followed in 2004, directed by
Scott Ziehl, starring
Kerr Smith and
Kristina Anapau, as Cassidy Merteuil, cousin to Kathryn.
None of the cast from the original appeared in the sequels.
Canceled sequel series
NBC
The National Broadcasting Company (NBC) is an American commercial broadcast television and radio network serving as the flagship property of the NBC Entertainment division of NBCUniversal, a subsidiary of Comcast. It is one of NBCUniversal's ...
picked up a television
pilot
An aircraft pilot or aviator is a person who controls the flight of an aircraft by operating its Aircraft flight control system, directional flight controls. Some other aircrew, aircrew members, such as navigators or flight engineers, are al ...
for a continuation of the film's storyline in October 2015. The pilot was set seventeen years after the events of the film and sees Bash Casey, son of Sebastian Valmont and Annette Hargrove, discover his late father's journal. Upon discovering this he is thrown into a world of lies, sex, and power. The potential series was to have Kathryn Merteuil, Bash's step-aunt, attempt to gain power of Valmont International.
In February 2016,
Taylor John Smith and
Samantha Logan were cast, with Smith playing the male lead role of Bash Casey, Sebastian Valmont and Annette Hargrove's son. Gellar reached a deal with producers to reprise her role as the female lead, Kathryn Merteuil. In March,
Kate Levering was cast to replace Witherspoon for the role of Annette Hargrove.
Several months later, on October 31, NBC passed on the project and the series did not go forward.
Amazon Prime Video reboot series
In October 2021, a television series
reboot
In computing, rebooting is the process by which a running computer system is restarted, either intentionally or unintentionally. Reboots can be either a cold reboot (alternatively known as a hard reboot) in which the power to the system is physi ...
of ''Cruel Intentions'' was in development for IMDb TV (now
Amazon Freevee
Amazon Freevee (stylized as freevee and fv, also shortened as Freevee, formerly known as IMDb Freedive and IMDb TV, and sometimes spelled FV) is an American Free ad-supported streaming television, ad-supported video on demand, video-on-demand ( ...
). In April 2023, the reboot was given a series order.
It premiered on Amazon Prime Video on November 21, 2024.
Musical
A 1990s
jukebox musical
A jukebox musical is a stage musical or musical film in which a majority of the songs are well-known, pre-existing popular music songs, rather than original music composed for the musical.
Some jukebox musicals use a wide variety of songs, while ...
by Kumble, Rosin, and Ross, was first staged in 2015. After two runs in Los Angeles and a pop-up engagement in New York, ''
Cruel Intentions: The '90s Musical'' made its
Off-Broadway
An off-Broadway theatre is any professional theatre venue in New York City with a seating capacity between 100 and 499, inclusive. These theatres are smaller than Broadway theatres, but larger than off-off-Broadway theatres, which seat fewer tha ...
debut at the Greenwich Village nightclub
Le Poisson Rouge in November 2017 and ran through April 2018. Set to pop and rock
hits of the 1990s and songs from the film's soundtrack, the plot follows the manipulations of Sebastian Valmont and Kathryn Merteuil, out to destroy anyone who gets in their way.
See also
*
Blonde versus brunette rivalry
References
External links
*
*
*
*
{{Authority control
Cruel Intentions (franchise)
1990s American films
1999 directorial debut films
1999 LGBTQ-related films
1999 romantic drama films
American high school films
American romantic drama films
American teen drama films
American teen LGBTQ-related films
American teen romance films
Columbia Pictures films
English-language romantic drama films
Films about incest
Films about siblings
Films about the upper class
Films about virginity
Films adapted into plays
Films adapted into television shows
Films based on French novels
Films based on romance novels
Films based on works by Pierre Choderlos de Laclos
Films directed by Roger Kumble
Films produced by Neal H. Moritz
Films scored by Edward Shearmur
Films set in Manhattan
Films shot in Los Angeles
Films shot in New York City
Films shot in Toronto
Films with atheism-related themes
Newmarket films
Original Film films
Teensploitation
Works based on Les Liaisons dangereuses
Teen Choice Award winning films