Question: Kathryn Merteuil's rold as Kathryn serves as the primary antagonist in a film released in what year?

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Sylar: Sylar (Gabriel Gray) is a fictional character and a primary antagonist of the NBC science fiction drama series "Heroes".  Portrayed by Zachary Quinto, he is a superpowered serial killer who targets other superhumans in order to steal their powers.  He served as the primary villain of the first season and then as a recurring antagonist.  Over the course of seasons two, three and four, the writers depicted Sylar attempting at various times and under different circumstances to become a hero or curb his desire to kill, undergoing relapses at various stages.  In the series' penultimate episode he experienced over three years of penitence within a mental prison, and later identifies himself as a hero in what became the show's series finale due to cancellation.

Emma Spool: Emma Spool is a fictional character created by director Tom Holland for the 1983 film "Psycho II".  She serves as the primary antagonist, and is portrayed by Claudia Bryar.  More attention is given to her character in "Psycho III", although she only appears as a corpse and a voice.

Bowser Jr.: Bowser Jr. (known as Koopa Jr. (Japanese: クッパJr.  , Hepburn: Kuppa Junia ) in Japan, or sometimes simply Junior, is a video game character who appears in Nintendo's "Mario" franchise as an antagonist.  As his name implies, he is the son of the series' primary antagonist, Bowser.  Since his debut in "Super Mario Sunshine", Bowser Jr. has been a recurring character in the "Mario" series, and has been made playable in several spin-offs, such as "Mario Superstar Baseball", "Mario Strikers Charged", and "Super Smash Bros. for Nintendo 3DS and Wii U".  He wants to do nothing more than his father's will (kidnap Princess Peach and defeat Mario).

Crimson King: The Crimson King, known to some as Los' or Ram Abbalah, is a fictional character created by Stephen King.  He is the primary antagonist of King's eight-volume "Dark Tower" series, as well as the novels "Insomnia" and "Black House".  Described as "Gan's crazy side", the Crimson King is the ultimate ruler of the Red (also called the Random and the Outer Dark), and the archetypal embodiment of evil in Stephen King's fictional multiverse.  His goal is to topple the Dark Tower which serves as the linchpin of time and space, destroying the multitude of universes which revolve around it so that he can rule in the primordial chaos which follows.

Andrew Ryan (BioShock): Andrew Ryan is a fictional character in the "BioShock" video game series developed by Irrational Games.  He serves as the primary antagonist of the first half of the first "BioShock" and a minor character in its sequel, "BioShock 2".  Ryan is an idealistic business magnate in the 1940s and 1950s; seeking to avoid scrutiny from governments and other oversight, he ordered the secret construction of an underwater city, Rapture.  When Ryan's vision for a utopia in Rapture collapsed into dystopia, he hid himself away and used armies of mutated humans, "Splicers", to defend himself and fight against those resisting him, including the player-character Jack within the first game.

Cruel Intentions 3: Cruel Intentions 3 is a 2004 American teen drama film directed by Scott Ziehl and released direct-to-video in 2004.  Despite its name, the film has almost no relation to the previous films in the series, except for the shared themes and the lead character in this film, Cassidy Merteuil, who is a cousin of one of the characters from the first film, Kathryn Merteuil.

T-3000: The T-3000 is a fictional cyborg assassin, serving as the primary antagonist in "Terminator Genisys", the fifth installment in the "Terminator" series, portrayed by Jason Clarke.  In the film, the T-3000 is an alternate timeline counterpart of Skynet's (portrayed by Matt Smith) nemesis John Connor (also portrayed by Clarke), created after Skynet infects a variant of Connor with nanotechnology and fractures the timeline.  T-3000 also serves as a foil personality to "Guardian" (a reprogrammed T-800 portrayed by Arnold Schwarzenegger), a protagonist who is somewhat similar to T-3000 but also opposite in many ways, of their relationship dynamics with Sarah Connor (portrayed by Emilia Clarke) and Kyle Reese (portrayed by Jai Courtney).

Cruel Intentions: Cruel Intentions is a 1999 American romantic teen drama film starring Sarah Michelle Gellar, Ryan Phillippe, Reese Witherspoon, and Selma Blair.  The film is an adaptation of "Les Liaisons dangereuses", written by Pierre Choderlos de Laclos in 1782, but set among wealthy teenagers attending high school in modern New York City instead of 18th century France.

Kathryn Merteuil: Kathryn Merteuil is a fictional character who appears in "Cruel Intentions" and "Cruel Intentions 2", portrayed by actresses Sarah Michelle Gellar and Amy Adams, respectively.  Based on the Marquise Isabelle de Merteuil in Pierre Choderlos de Laclos's "Les Liaisons dangereuses", Kathryn serves as the primary antagonist of the series.

Cruel Intentions (pilot): Cruel Intentions is an American drama pilot that was in production for NBC.  It acted as a sequel to 1999 film of same name, with Sarah Michelle Gellar reprising her role of Kathryn Merteuil.

Supporting paragraphs: Kathryn Merteuil Cruel Intentions
Answer: 1999