- Swoosie Kurtz also appeared in Dangerous Liaisons (1988) which, like this film, is based on the Choderlos de Laclos novel "Les liaisons dangereuses".
- The magazine in which Valmont finds the article that Annette wrote on virginity has Jennifer Love Hewitt on the cover. Both Ryan Phillippe and Sarah Michelle Gellar starred with her in I Know What You Did Last Summer (1997)
- The pool in the movie, at the time of filming, was only about 40 degrees Fahrenheit.
- Toward the end of the film when Kathryn tells Ronald that Sebastian had hit her, the actual scene of Sebastian striking her was filmed, but it was deleted afterwards because the dialogue from Sebastian during this part didn't fit his character.
- John Ottman's score was originally used during the trailer, however his score was rejected shortly before the film was released and was replaced by Ed Shearmur.
- Porn star Alisha Klass appeared as a cheerleader, but her brief scene was cut. You can see a glimpse of her in the lower right hand part of the screen when Sebastian is talking to Annette on the phone.
- Sebastian sitting in a wheelchair by the pool and listening to Ludwig van Beethoven's 9th Symphony is a reference to Stanley Kubrick's A Clockwork Orange (1971). In the end of the movie the old man in a wheelchair (Mr. Alexander), whose wife Alex and his droogs raped, is torturing Alex by playing the 9th Symphony as Alex is upstairs locked up in a room.
- The scene in which Annette slaps Sebastian was also unscripted. Reese Witherspoon and Ryan Phillippe were so into their scene that she slapped him unexpectedly, and Phillippe's reaction is genuine. He was so into the scene that right after the director said cut, he went behind the set and threw up. The director left the scene in the final cut.
- Despite previous reports, Reese Witherspoon was not pregnant during filming. The movie filmed from 9 June 1998 - 15 July 1998, and Witherspoon had her daughter Ava on 9 September 1999. A full year after filming the movie. She was, however, pregnant, when they did the press tours for the film.
- Neal H. Moritz contractually agreed to the film being rated R, and nothing less. Sony (the studio) agreed.
- In the original script, the scene where Sebastian and Annette meet at the pool there is a reference to Ayn Rand's "The Fountainhead". When Sebastian asks Annette what she is reading she replies, "The Fountainhead." And when Sebastian compliments the book, she is surprised he knew the novel. Sebastian goes on to say, "I think the scene where Howard Roark makes love to Dominique Francon is the most romantic work in all literature." Annette replies, "Romantic? He rapes her." And Sebastian finishes with, "That's a matter of opinion."
- Roger Kumble initially wrote the script in 12 days.
- The final straw in snagging Christine Baranski, who only had to work three days, was that her daughters were big "Buffy the Vampire Slayer" (1997) fans and were giddy that she could work with Sarah Michelle Gellar.
- The music near the very end of the movie during the funeral eulogy is "Bittersweet Symphony" by The Verve.
- Selma Blair who plays the role of the young freshman Cecile is older than both Sarah Michelle Gellar and Ryan Phillippe by 5 and 3 years respectively.
- Fred Norris, head writer and cast member of The The Howard Stern Show (1987) (TV), has a small part, credited as the Meter Maid - Ryan Phillippe is a huge Howard Stern fan.
- The kissing scene between Sarah Michelle Gellar and Selma Blair, ranked the film at #32 on Entertainment Weekly's "The 50 Sexiest Movies Ever" (issue #1023, November 28, 2008).
- The Valmount townhouse interiors were built and shot on sound stages in Los Angeles while the exterior scenes were filmed in New York City.
- Neal H. Moritz, who had worked on I Know What You Did Last Summer (1997) help cast the film. His first choices were Ryan Phillippe and Sarah Michelle Gellar who also starred in Summer.
- The film was shot in a six week period.
>>> WARNING: Here Be Spoilers <<<
Trivia items below here contain information that may give away important plot points. You may not want to read any further if you've not already seen this title.
- SPOILER: One version of Roger Kumble's screenplay had an ending where Annette, instead of publishing the journal and crushing Kathryn, keeps it to herself and announces her cruel intentions to play games on Kathryn under the threat of revealing the contents.
- SPOILER: After her public humiliation, Kathryn Merteuil's cross gets pulled open and her cocaine falls out, referencing the scene in Dangerous Liaisons (1988) in which the similarly disgraced Marquise de Merteuil (Glenn Close) sweeps a cloud of white powder off her dressing table.
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