8. Hard Eight
Anderson's debut is a hardboiled tale of gambling in Las Vegas starring Philip Baker Hall, John C. Reilly, Gwyneth Paltrow, and Samuel L. Jackson.
Following professional gambler Sydney (Philip Baker Hall) as he takes the young and desperate John Finnegan (John C. Reilly) under his wing, Hard Eight is a taut drama with noir elements, like an updated slice of one of Hemingway's more hardboiled short stories. There are twists and turns, but for all its plot work, it is the performances that shine in Hard Eight, especially those of Hall and Reilly as well as a very small role for P.T.A. regular Philip Seymour Hoffman.
Hard Eight is an impressive debut, with compelling character work and a slick style you'd expect from Anderson. The main reason it is at the bottom of this list is simply because Hard Eight has less to say than Anderson's other films; it doesn't try to be anything more than an engaging crime story (which displays admirable focus for a first time filmmaker), and as such suffers by comparison with Anderson's later films, which burrow deep into more profound territory and themes.