Igby Goes Down once again. I've seen it three times now. I really click with the humor and enjoy the wonderful ensemble cast in this dark, sad story about a fucked up rich family.
Igby's mom (Susan Sarandon) is dying of cancer. She has been an self-absorbed hardened mom to Igby and his very pretension older brother. Their father had a serious break with reality when they were children and has been in a mental hospital for years. Igby keeps getting kicked out of expensive high schools, and his long-time family friend (Jeff Goldblum) takes him under his wing. Goldblum is a rich and charming asshole with all the great lines. He has a mistress he keeps in a soho loft, Amanda Peet, whose drug use starts to get really messy. Igby is in love with her, as well as with Sukie, a college student played by Claire Danes, who is also romantically involved with Igby's brother. Throughout the movie you see Igby terrified of becoming like the adults around him, and while deeply scared of going crazy like his father, through flashbacks you see Igby develop compassion for this broken man.