George Norton is a low-level bumbler who works for Chicago crime boss Charley Barker. A well-dressed mama's boy, George is in good standing with Barker, even gaining a promotion, until an incident that costs the mob a million dollars.
Pete Turner (Weatherred) is the leader of a good-deed group, the ButterCream Gang, in the small rural town of Elk Ridge. Before he moves away to live with his aunt (affectionately known as Aunt Spaghetti due to her famous ketchup spaghetti sauce) in Chicago, Pete bikes over to their treehouse, searching for Scott Carpenter (Johnson), Eldon Flowers (Blaser), and Lanny Glenn (Glenn). He climbs up to the tree, being surprised by the rest of the gang. After a brief discussion, Pete nominates Scott to become the new leader of their small band. At the bus station, Pete says good-bye to all his family and friends, then departs on the bus to Chicago.
Gavin Ransom (Noah Wyle) is a successful real estate developer who has made a tidy fortune putting up gated communities filled with expensive suburban homes all over California. Ransom intends to put up another such development in the as-yet-untouched hillsides of Northern California's Marin County, and, just as he's expected, a number of folks living nearby are objecting to the project, including his sister Olive (Illeana Douglas), an environmental activist who has sided with longtime resident Eileen Boatwright (Cloris Leachman) and progressive lawyer Sybil (Jane Lynch) against the development. Olive and her compatriots get some unexpected support when Zoe Tripp (Kate Mara), a modern folk singer and the daughter of old-school Marin County hippies (Keith Carradine and Valerie Perrine), takes an interest in their protests and begins singing out against Gavin's proposal with guitar in hand. Gavin unexpectedly finds himself growing powerfully infatuated with Zoe, and Olive, a long-closeted lesbian, is equally taken with her; consequently, as the siblings battle against building several dozen cookie-cutter mansions, they also wage a private war for the affections of the young songstress.
Mrs. Callahan (Dressler) and Mrs. Murphy (Moran), are a couple of feuding tenement housewives working to keep control of their many children. Dan Murphy (Gray) falls in love with Ellen Callahan (O'Neill), and then later disappears after Ellen is pregnant. Mrs. Callahan (Dressler) decides to adopt the baby to save her daughters reputation, but later finds out that the baby is not illegitimate after all.
Kate Loughlin is a vivacious young actress struggling to get her big break in the London film industry. When she lands an audition for the lead role in a massive movie franchise based on the 'Prince of Chaos' novels by legendary author Horatio King, she goes after the opportunity with all guns blazing.