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I liked The Last Days of Disco (1998) OK, but Whit's first two films are much better. That same kind of low-key, deadpan, ironic sense of humor is there, and his diologue has a very distinct music to it, but Metropolitan (1990) and Barcelona (1994) are more complete and satisfying efforts. For me, Barcelona is his best film to date.
All three films have been at least loosely autobiographical. He was born to a kind of privelege as the son of a politician and debutante traveling in those posh circles, as a young man he spent nights in the Studio 54-fueled disco landscape of Manhattan, and he met his Spanish wife while working in Barcelona.
And everytime I see Whit's movies I'm amazed that Chris Eigeman isn't a bigger star, even just in the indie film world. I think he should be the male equivalent of Parker Posey, appearing in dozens of flicks, working constantly. He did make a stab at the mainstream when he co-starred on the ill-titled ABC sitcom "It's Like, You Know..." (1999). That show didn't last but half a season, and it's only remembered (if at all) as the show where Jennifer Grey played herself and made a running gag of her nosejob that altered her appearance from the Dirty Dancing/Ferris Bueller's Day Off gal we all knew.
Eigeman has a recurring guest role on "Malcolm in the Middle", but I'd like to see him in more projects. Taylor Nichols is Stillman's other alter ego - though his role in Disco is basically only a cameo, and he has shown up in more mainstream fare (Jurassic Park III, Congo, The American President and HBO's "The Mind of the Married Man"). Nichols and Eigeman work well together, deliver Stillman's stylized dialogue perfectly, and I hope Whit uses them again prominently.
But Whit hasn't made a movie since The Last Days of Disco. I'm definitely a fan and await his next effort, but Stillman isn't as well known as he should be. His voice and those three movies are wonderful, but difficult to market into any kind of measurable "success". The Last Days of Disco did get some decent publicity and distribution (compared to the first two films), unfortunately it was his weakest work thus far and probably didn't have the same kind of chance Barcelona would have given the same profile. He does have a fanbase, but he's still pretty much a secret.
So yeah, seek out Barcelona and Metropolitan. Barcelona did get an R1 DVD release, but Metropolitan may be more difficult to find as it is only available on VHS and has no recognizeable names in the cast to lure Blockbuster to stock it on their shelves (at least Barcelona has a role for Mira Sorvino, and Disco has Kate Beckinsale). Well worth tracking 'em down.
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"Film is a disease. When it infects your bloodstream it takes over as the number one hormone. It bosses the enzymes, directs the pineal gland, plays Iago to your psyche. As with heroin, the antidote to Film is more Film." - Frank Capra