Igby (Kieran Culkin) is tired of being shipped from one private school to the next by his wealthy, detached mother (Susan Sarandon). After a few failed escape attempts, Igby ends up living in a NYC loft with a woman (Amanda Peet) who is sleeping with his godfather (Jeff Goldblum). While Igby tries to deal with the reality of his dysfunctional life, including an institutionalized father (Bill Pullman), he grows close to another outsider (Claire Danes), only to have her stolen away by his "fascist" older brother (Ryan Phillippe). Directed by Burr Steers. With Rory Culkin and Jared Harris. Categories: Comedy, Drama, Independent Film. Year: 2002.

Kieran Culkin in Igby Goes Down
Homer Wells (Tobey Maguire) grows up in an orphanage and becomes a skilled physician under the tutelage of his mentor, Dr. Larch (Michael Caine). Desiring a life outside the only home he has ever known, Homer falls in love for the first time and faces difficult decisions force him to realize that he will never fully escape his past. Directed by Lasse Hallström. With Charlize Theron, Delroy Lindo, Paul Rudd, Kieran Culkin and Erykah Badu. Categories: Drama, Romance. Year: 1999.

Kieran Culkin in The Cider House Rules