The cynical son of an upper-class New York family bedeviled by booze, pills and mental illness strikes out on his own in this caustic, darkly comic drama. Igby Slocomb (Kieran Culkin) and his older brother, Oliver (Ryan Phillippe), are are in the process of killing their mother, Mimi (Susan Sarandon). Flashbacks delineate Igby's troubled childhood: Speed-freak Mimi and her depressed husband, Jason (Bill Pullman), snipe at each other endlessly until Jason attempts suicide before Igby's very eyes and takes up residence in a mental hospital. Igby grows into a rebellious youth, gets kicked out of several boarding schools and ends up in a hellish military academy. After one failed escape attempt, he heads to New York City and hides out in the apartment of Rachel (Amanda Peet), the heroin-addled mistress of his godfather, D.H. (Jeff Goldblum). Oliver locates the young scoundrel and informs him that Mimi is suffering from cancer. Unperturbed, Igby continues his slacker existence -- and his romance with Sookie (Claire Danes), a hipper-than-thou undergraduate who finds herself torn between Igby and Oliver. As Igby gets drawn further into the mind games and hypocrisy of the adult world, his already jaded outlook grows even darker. He takes to dealing smack and hanging out with a cross-dressing performance "artist" (Jared Harris). Ultimately, though, Mimi's impending death draws him back into the family fold for unexpected revelations and realizations. Written and directed by first-time filmmaker Burr Steers, Igby Goes Down features Rory Culkin, Kieran's brother, as the young Igby.