My wife just had me watch Barcelona over the weekend, a film with its own meta-level discussion of other films and film criticism (don't miss Fred and Ted discussing text and subtext). I was intrigued enough by Stillman to do a little surfing. Here's a link to a review of Doomed Bourgeois in Love, a book of essays on Stillman, which sounds like it will be worth reading. Editor Mark Henrie argues that "The perplexity that animates each of Stillman's films is how to find our way, how to live well, when the cake of custom has been broken. . . . Perhaps in an age such as ours, it is not tragedy but comedy which is the mature response." There is also an NRO interview and an Onion AV Club interview. Viva la comedia.
As someone on IMDB once commented, the name Whit fits the nature of his films, but just as fitting is the name "Stillman", for the characters populating his scripts are frequently people going nowhere not only physically but intellectually, philosophically and morally. Like the few others I know that have seen it, I could barely stay awake till the end of the superficial and saccharine "Barfelona", but despite everything the protagonists go through in the film by the end they seem not any more likeable, wiser, or less shallow than they were at the begining of the film.
However, the film serves as an accurate portrayal of the arrogant, ignorant, self centered mindset of the current bunch of preppy scum driving America's foriegn policy to hell.