Watch Cruel Intentions (1999): stream Cruel Intentions (1999) on Hulu, Hoopla, Kanopy, or rent on Apple TV+ or Fandango At Home. Compare all streaming options for this movie on WhereCanIWatch.tv.
Cruel Intentions
In the game of seduction, there is only one rule: Never fall in love.
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HD · Included
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You can watch Cruel Intentions (1999) for free on Hoopla, rent on Apple TV+, or buy on Apple TV+.
Slaking a thirst for dangerous games, Kathryn challenges her stepbrother, Sebastian, to deflower their headmaster's daughter before the summer ends. If he succeeds, the prize is the chance to bed Kathryn. But if he loses, Kathryn will claim his most prized possession.
This teen drama swaps earnest coming-of-age sentiment for a razor-sharp game of psychological warfare and predatory manipulation. Wealthy step-siblings turn high school social hierarchies into a lethal playground for their twisted bets.
Trailer
Director
Roger Kumble
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7 options ranked by value · 🇺🇸 United States
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Last verified 11 days ago
Cruel Intentions
In the game of seduction, there is only one rule: Never fall in love.
You can watch Cruel Intentions (1999) for free on Hoopla, rent on Apple TV+, or buy on Apple TV+.
IMDb
6.8/10
RT Critics
54%
RT Audience
80%
Metacritic
Director
Roger Kumble
7 options ranked by value · 🇺🇸 United States
Keep browsing: New Releases · Popular Movies · Drama · Romance
bet · virgin · drug abuse · sibling relationship · based on novel or book · sexual obsession · upper class · cynic · sadistic · eroticism
Cruel Intentions is streaming on Hulu. Watch Cruel Intentions for free on Hoopla. Watch Cruel Intentions for free on Kanopy. Rent Cruel Intentions on Apple TV+. Rent Cruel Intentions on Fandango At Home. Buy Cruel Intentions on Apple TV+. Buy Cruel Intentions on Fandango At Home. Cruel Intentions is not currently available on Netflix, Max, Disney+, Prime Video. Availability last verified July 9, 2026.