Cruel Intentions Movies in Order Film series·1999–2004 3 films from 1999 to 2004, 4 hours of viewing in all. Listed in release order. In release order 1 Cruel Intentions 1999 1 hr 37 min Directed by Roger Kumble Rent or buy DVD & Blu-ray 2 Cruel Intentions 2 2000 1 hr 23 min Directed by Roger Kumble Rent or buy DVD & Blu-ray 3 Cruel Intentions 3 2004 1 hr 22 min Directed by Scott Ziehl Rent or buy DVD & Blu-ray Film data from Wikidata.