2. Boogie Nights
My favorite of Anderson's movies and one of my all time favorites in general, Boogie Nights is an amazing film in general but what really makes it such a testament to the prowess of its director is it was only Anderson's second feature yet it looks like it was made by a director who's been working for thirty years. The opening of the film alone looks like the work of a seasoned professional: the long continuous shot that goes into a night club from the street while introducing every major character and some side characters of the film in a span of about three minutes is glorious. If Scorsese hadn't of set the bar so high with Goodfellas and the Copacabana shot I would be tempted to say that Boogie Nights is the best film of the 90s but the fact that it gets such heavy comparison to Scorsese and Altman without being called a ripoff is an example of how amazing it is. Anderson's skills as a writer are the most evident as well with Boogie Nights. He writes some of the most anguished yet lovable characters ever put to film and they never come off as anything less than real people even though they're living in a very unconventional environment. This is all due to Anderson's mastery of the cinematic medium as a writer or director.