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.
Sarah Michelle Gellar ( ; born April 14, 1977) is an American actress, producer, and entrepreneur.
 After being spotted by an agent at the age of four in New York City, she made her acting debut in the made-for-TV movie "An Invasion of Privacy" (1983).
 Gellar went on to appear in numerous television series and commercials.
 Her first leading part was in the 1992 miniseries "Swans Crossing", for which she was nominated for two Young Artist Awards, and her television breakthrough came in 1993, when she originated the role of Kendall Hart on the ABC daytime soap opera "All My Children", winning the 1995 Daytime Emmy Award for Outstanding Younger Actress in a Drama Series.
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.
Dawn Summers is a fictional character created by Joss Whedon and introduced by Marti Noxon and David Fury on the television series "Buffy the Vampire Slayer", portrayed by Michelle Trachtenberg.
 She made her debut in the premiere episode of the show's fifth season and subsequently appeared in every episode of its remaining three seasons.
 Within the series, Dawn is the little sister of main character Buffy Summers (Sarah Michelle Gellar), a girl chosen by fate to be a vampire Slayer.
 Whedon introduced Dawn to the series because he wanted to introduce a character with whom Buffy could have an intensely emotional non-romantic relationship.
"Moonshine River" is the first episode of "The Simpsons"' twenty-fourth season.
 It originally aired on the Fox network in the United States on September 30, 2012.
 In the UK and Ireland, the episode aired on Sky 1 on 24 March 2013 with 1,295,000 viewers, making it the second most watched program that week.
 The episode has ten guest stars, Ken Burns, Zooey Deschanel, Sarah Michelle Gellar, Anne Hathaway, Maurice LaMarche, Don Pardo, Natalie Portman, Kevin Michael Richardson, Al Roker and Sarah Silverman.
 Deschanel, Gellar, Hathaway, Portman and Silverman reprise their roles as Bart's previous love interests, Mary Spuckler (from "Apocalypse Cow"), Gina Vendetti (from "The Wandering Juvie"), Jenny (from "The Good, the Sad and the Drugly"), Darcy (from "Little Big Girl") and Nikki (from "Stealing First Base"), respectively.
 This is the second episode in which the Simpsons go to New York City, the first episode being "The City of New York vs. Homer Simpson".
 The title is a parody of the 1961 Academy Award-winning song, "Moon River".
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.
The Crazy Ones is an American sitcom created by David E. Kelley, and stars Robin Williams and Sarah Michelle Gellar.
 The single-camera series aired for one season on CBS, from September 26, 2013, to April 17, 2014.
 It was part of the 2013–14 American television season as a Thursday night 9:00 pm Eastern / 8:00 pm Central entry.
 Bill D'Elia, Dean Lorey and Jason Winer served as executive producers for 20th Century Fox Television.
 The episodes are loosely based on the life experiences of John R. Montgomery while he worked at Leo Burnett advertising in Chicago.
Scream 2 is a 1997 American slasher film directed by Wes Craven and written by Kevin Williamson.
 It stars David Arquette, Neve Campbell, Courteney Cox, Sarah Michelle Gellar, Jamie Kennedy, Laurie Metcalf, Jerry O'Connell, Jada Pinkett and Liev Schreiber.
High Stakes (also known as Melanie Rose) is a 1989 thriller-drama film starring Sally Kirkland, and features Sarah Michelle Gellar in a supporting role.
 Kathy Bates also has a minor role.
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.

Question: What year did Sarah Michelle Gellar play Kathryn Merteuil?
Answer: 1999