Explorers Bartholemew Hunt and Leslie Edwards are setting forth against nature across the country on a journey to the Pacific Ocean against rivals Lewis and Clark. Along the way they have many mishaps and misfortunes.

In this study of Generation X manners, Lelaina, the valedictorian of her college class, camcords her friends in a mock documentary of posteducation life. Troy is her best friend, a perpetually unemployed musical slacker. Vickie is a manager at the Gap who worries about the results of an AIDS test, while Sammy has problems grappling with his sexuality. When Lelaina meets Michael, an earnest video executive who takes her homemade video to his MTV-like station, she must decide what she values--the materialism of yuppie Michael or the philosophical musings of Troy.

The film follows the rise to power of Daniel Plainview - a charismatic and ruthless oil prospector, driven to succeed by his intense hatred of others and desperate need to see any and all competitors fail. When he learns of oil-rich land in California that can be bought cheaply, he moves his operation there and begins manipulating and exploiting the local landowners into selling him their property. Using his young adopted son H.W. to project the image of a caring family man, Plainview gains the cooperation of almost all the locals with lofty promises to build schools and cultivate the land to make their community flourish. Over time, Plainview's gradual accumulation of wealth and power causes his true self to surface, and he begins to slowly alienate himself from everyone in his life.

Lester and Carolyn Burnham are on the outside, a perfect husband and wife, in a perfect house, in a perfect neighborhood. But inside, Lester is slipping deeper and deeper into a hopeless depression. He finally snaps when he becomes infatuated with one of his daughter's friends. Meanwhile, his daughter Jane is developing a happy friendship with a shy boy-next-door named Ricky, who lives with a homophobic father.