Funny / Cruel Intentions

• When Kathryn reminds Sebastian of whom her ex-lover Court is dating now. Smash Cut to Cecile in a childish sailor outfit standing next to a pickle costume mascot at the carnival. Waving to the camera and accidentally spilling her ice cream.
• Cecile's mom lets her personal prejudices get her off track during an angry rant:
  Bunny Caldwell: How dare you treat me with such disrespect! I got you off the streets and this is how you repay me?
  Ronald Clifford: Got me off the streets? I live on 59th and Park!
• Kathryn deliberately getting Sebastian all horny and then, when he says he hasn't won the bet yet, she just says "Down, boy" and walks off. The way he says "Oh, come on!" is hilarious.
  • Becomes slightly Harsher in Hindsight when you realise it's a Foreshadowing of the point where Kathryn is ready to screw him and he walks off. She takes it much worse than him and things get worse from there.
• The Running Gag of Cecile getting pushed or rolled off sofas and beds whenever she Glomps someone.
  • Cecile is generally hilarious because she is just so brainless and incompetent she can't even stop being Adorkable when she's being seductive.
  • Cecile saying in a dreamy state "Dr. King is my favorite." And the look on Kathryn's face in response to that.
• After the Practice Kiss, Cecile asks Kathryn if she wants to have a sleepover. Cue the Oh, Crap! look on Kathryn's face.
• The Nursing Home scene is a riot. Because you don't know whether or not what Sebastian said is true or if he was messing with her senility.
  Mrs. Sugarman: Oh, did I ever tell you the time, when my late husband sent me...
  Sebastian: Yes, you already did, Mrs. Sugarman.
  Mrs. Sugarman: Oh, I did?
  Sebastian: Right after we played backgammon, Mrs. Sugarman.
  Mrs. Sugarman: Oh! We played backgammon?
  Sebastian: Uh huh. You beat me three times.
  Mrs. Sugarman: I did?
  Sebastian: Yup. Then I fucked your daughter.
  Mrs. Sugarman: Excuse me?
  Sebastian: I said, would you care for some water?
  Mrs. Sugarman: No, thank you.
• When Cecile returns home in the morning with her clothes rumpled and hair disheveled:
  Bunny Caldwell: Jesus Christ, where have you been?
  Cecile Caldwell: Shopping?
• The musical embraces the Narm Charm of the original and is arguably better for it.
  • Greg and Blaine's romantic love duet... "I Want It That Way." Try to listen without giggling.
  • Cecile's deliciously hammy performance of "I'll Make Love to You," and Sebastian's utterly confused reaction.
  • Mrs. Caldwell's blatant racism becomes hysterical when she starts singing "No Scrubs." We probably don't even want to know how many rehearsals it took for the actors to get through it without corpsing.
    • The Act One closer, "Only Happy When It Rains," is mostly Awesome Music, but then it becomes a Reprise Medley of nearly every song in Act One... and, yes, Mrs. Caldwell is singing "No Scrubs" again.
• In 2020, Sarah Michelle Gellar and Selma Blair re-created their famous kiss for a parody skit.

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