Cruel Intentions

1h 38m · 1999 · Directed by Roger Kumble · 3.3 / 5 on Letterboxd

Cruel Intentions (1999) runs 1h 38m, directed by Roger Kumble. It is one of 3,647 films in the 100 Minute Movies catalog — every one rated 3.0 or higher by Letterboxd members and short enough to finish in an evening.

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.

Genres: Drama, Romance

Where to watch: Hulu, Netflix (US, checked 9 July 2026)