Cast
Zach Braff as Andrew Largeman, a depressed, heavily medicated, struggling young actor who waits tables in a Vietnamese restaurant. When he was nine years old, he accidentally paralyzed his mother by pushing her over a dishwasher door. He has not cried or felt any significant emotions for several years, mainly as a result of the medication he has been supplied with by his estranged father.
Natalie Portman as Samantha "Sam", an eccentric epileptic and compulsive liar, who openly admits to her casual dishonesty and frequently ponders what makes her do it. She says she works at a law office as a paralegal, and lives with her equally peculiar mother and her adopted African sibling, Titembay.
Peter Sarsgaard as Mark, an old school friend of Andrew, now working as a grave-digger. He still lives with his mother and smokes marijuana, frequently attending wild parties; he also makes money by stealing jewelry from the people he buries and exploiting loopholes in store return policies.
Ian Holm as Gideon Largeman, Andrew's father and psychiatrist, whose passive demeanor hides deep-seated grief that his family has not been "happy". He still thinks Andrew's anger is responsible for his late wife's paralysis and has tried to use lithium and other medications to "control" Andrew's emotions in a futile attempt to bring happiness to his family.
Jean Smart as Carol, Mark's mother, a recovering alcoholic, who sees a wealth of potential in her son.
Armando Riesco as Jesse, another school friend of Mark and Andrew who has made a fortune and bought a mansion with money he has earned from inventing a silent alternative to Velcro fabric.
Jackie Hoffman as Sylvia Largeman: Andrew's aunt, who sings the Commodores's "Three Times a Lady" at her sister-in-law's funeral.
Method Man as Diego, a bellhop at a luxury hotel who hosts peeping sessions of various hotel rooms.
Alex Burns as Dave, another old school friend who now works as a grave-digger with Mark.
Ron Leibman as Dr. Cohen, a neurologist whom Andrew visits at the beginning of the film.
Denis O'Hare in a cameo appearance as Albert, one of the "guardians of the abyss".
Jim Parsons as Tim, an old acquaintance of Mark and Andrew, and the boyfriend of Mark's mother, who works as a knight at Medieval Times.
Michael Weston as Kenny the Cop, a former classmate of Andrew's from high school; he is now employed as a police officer in their New Jersey neighborhood.
Ann Dowd as Olivia, Sam's mother.
Ato Essandoh as Titembay, Sam's adopted brother.
Geoffrey Arend as Karl Benson, another former high-school classmate of Andrew's; works at Handi-World.