Though he is best known for two ambitious ensemble pieces such as Boogie Nights and Magnolia, writer/director Paul Thomas Anderson was first noticed thanks to a low-key, unpretentious character study, a gem called Sydney.
The film takes its title from the main character, a lonely elder man played by Philip Baker Hall. At a diner he runs into John (John C. Reilly), a poor fella who has just lost all his money. Sydney buys him coffee, and after a little chat he persuades him to come to Reno. Once there, they manage to get a free room and under Sydney's tutelage John quickly becomes a successful gambler. All's well until he falls in love with Clementine (Gwyneth Paltrow), a waitress and part-time prostitute, and trouble ensues with a gangster named Jimmy, meaning Sydney will have to come up with something extreme to save his protégé.
For a first-time director Anderson shows great skills and confidence: even though he doesn't do much but follow four characters, he frames each shot to perfection and proves he is every bit as good as Scorsese at staging tracking shots (a thing he perfected on his next two features). But style doesn't really matter here: the important thing is that the audience cares for the story, and this essentially happens courtesy of sublime dialogue and great acting.
Anderson fought really hard to keep the movie's original title (and partially failed, which is why the film is known as Hard Eight in some countries), and the reason is clear from the beginning: the picture rests entirely on Hall's shoulders, and he carries it admirably. His performance is nuanced and genuine, and he manages to ensnare the viewer even when we are not sure what his motives are (and once they are revealed, it is not that important). Reilly is equally good, in a turn that opened his way to becoming one of the most reliable character actors in Hollywood, and the same intensity emerges from Paltrow and Jackson, the latter in particular adding extra dramatic flesh to what could have been a rehash of his more famous roles (Pulp Fiction etc.). Even Philip Seymour Hoffman, who has a brief but memorable role as a cocky gambler, gets his opportunity to shine, showing beyond any doubt that Anderson has a great eye for casting. He also knows how to write: the dialogue flows freely and seamlessly between the players, spawning some of the most affecting, realistic conversations ever heard in a movie, although the director can't resist the temptation to insert a couple of in-jokes as well (in one scene, Hall mentions two characters he wound up playing in Boogie Nights and Magnolia).
Overall, a very good film, and a must-see for PT Anderson fans: like many other directors who rose to fame in the '90s (Tarantino, Rodriguez, Bryan Singer) he proved right from the start what he was capable of, and has never disappointed the audience since that.
