Worry overtook me late last week as I drove into Woodstock. Tie-dye and other hippie kitsch closed my throat like a bee sting; the farmhouses, changing leaves and rolling Catskills imposed their remove with every extra mile I pulled further away from New York. All the earlier endorsements and praise exhorting me to cover the Woodstock Film Festival congealed to static between my ears. I wheezed and kvetched, unsure of how to make it through my bucolic weekend exile.

In the end, the abundance of fine movies certainly helped. It's anyone's guess if the eighth annual festival was its best to date, but the balance of distributed heavy hitters and ambitious upstarts -- and the community that flocked to them -- bespoke an ideal harmony that fests don't cultivate overnight. Moreover, the staff's hospitality soothed the immediate psychic trauma of bohemian village excess. I lived to tell, even enjoy.

The roaming clusters of brilliant New York filmmakers didn't hurt either. Take Sol Tryon for starters, whose outrageous The Living Wake had its East Coast premiere Friday night. Starring comic Mike O'Connell in what should be, if there's any justice in the world, a star-making role as the terminally ill, defiantly delusional outcast K. Roth Binew, the film traces the final 24 hours (or are they?) of Binew's life as his friend Miles (Jesse Eisenberg) chauffers him on a grand tour of goodbyes through a perpetually autumn parallel universe -- in a rickshaw. Forsaken by his family and beset with confessional, near-Shakespearean levels of woe, Binew compels indulgence from characters and viewers alike; similar to The Jerk's iconic Navin Johnson, his legend thrives in the comic alchemy of fantasy, failure and the cults of personality each quality inspires.

The culmination of his "living wake" is one of the great comedic set pieces of the last decade, a sublimely art-directed and choreographed dirge gone wrong. Tryon, O'Connell and co-writer Peter Kline (adapting the screenplay from O'Connell's one-man show) developed and refined the script for two years before finally shooting in Tryon's native Maine in fall 2005, steeping Binew's journey in the bittersweet chemistry of age, loneliness and optimism. "It had its difficult times for sure," said Tryon, also the Brooklyn-based producer of films by Adam Bhala Lough (Bomb the System, Weapons) and actor Mark Webber's just-wrapped directorial debut Explicit Ills. "Not necessarily in terms of wanting to move on to the next project, but wanting to get appreciation for this project. I felt like it was something that people would really get into and really enjoy -- something that was so original and different that I felt like I had to find a way to get people to see it and let the audience make the decision. The people who make that decision to 'allow' movies to be seen by people would have to take a chance."

Indeed, Woodstock was only the second festival to select The Living Wake since its Cinevegas premiere last summer, but the film has key devotees in that fest's influential programming chief Trevor Groth as well as Woodstock programmer Tom Quinn, himself an acquisitions exec at Magnolia Pictures. Meanwhile, in a cruel twist sort of befitting his character, O'Connell spent the weekend representing the film at the Austin Film Festival. "He's got one of the craziest minds you'll ever experience, and it's so much fun," Tryon said of working with his lead, sorely missed at Woodstock. "I've never met anyone who's as dedicated as he is. It's a pleasure to be able to work with him and experience his mind and his world. He's going to be one of the greats."

The Living Wake director Sol Tryon at Friday's Woodstock premiere (Photo: STV)

It's altogether possible, though his extended period in the indie distribution waiting room has me all kinds of dispirited. Like Carlos Reygadas' undistributed Silent Light, whose theatrical release Spout Blog writer Karina Longworth recently considered charging to her credit cards (she'll need at least a dozen, I hear), The Living Wake is just about one step removed from instant-classic status. That step is a gamble -- not even a leap of faith; it killed with my audience, won Tryon a directing prize at Cinevegas and has snowballing word-of-mouth and acclaim to recommend it. If it's not bought by the end of the year, I'm taking out a loan of my own.

Magnolia does in fact have the rights to Doug Pray's new documentary Surfwise, which chronicles the lives and times of the Paskowitz surfing clan. Eleven strong and headed by irascible octogenarian Dorian Paskowitz -- a legend of the sport since the 1950s -- the family traveled North America in a camper for nearly 20 years, setting up a famous surfing school while negotiating a choppy overlap of self-education, sexuality and health for their nine kids. Surfwise sustains the subcultural tone of Pray's best (Hype, Infamy) while adhering to compelling narrative conventions that have no real precedent in his work. But well-made as it is, its most telling component is the thinly veiled vanity behind its undertaking: At least three of the Paskowitz kids have dabbling film-industry interests, with Jonathan Paskowitz making his producing debut here. (In the Woodstock Q&A session he admitted originally planning a companion film for his father's recent book.) As such, the reunion that closes the film seems not only unimaginable in the face of the acrimony that precedes it, but almost wholly contrived. Revelation, not catharsis, is Pray's strong suit, and their collision in Surfwise yields an aftertaste as pleasant as a mouthful of salt water.

David Van Taylor's doc Good Ol' Charles Schulz, a PBS-ready profile of the late Peanuts creator, wowed with revelation of its own: The sources of torment undergirding Schulz's finest work, from dozens of viewings of Citizen Kane to his stage-managed ego and the brutal dissolution of his first marriage. Elsewhere, the Heeb Magazine-produced horror short Night of the Living Jews -- shot not far from the Bearsville Theater where it premiered -- drew a raucous local crowd that fled in yawning ambivalence around the 20-minute mark of the film it preceded, Ti West's crawling opus Trigger Man.

As featured in Surfwise, the Paskowitz clan in ostensibly happier times (Photo: Magnolia Pictures)

Among the panels I crashed, new Sidney Kimmel Entertainment boss Bingham Ray mysteriously backed out of Saturday's revealing distribution chat featuring Quinn, his NYC peers Wendy Lidell (International Film Circuit) and Ben Stambler (ThinkFilm) and Netflix's Ted Sarandos, whose billion-dollar crystal ball attracted questions about everything from his company's theatrical ambitions to the tenability of distributing short films online. "This is the right business model for that," he said. "The average viewing time for content online is about six minutes, and [viewers] are willing to accept embedded or pre-roll advertising for six minutes of viewing. I think that's really the only business model for short films."

If so, I may add Myna Joseph's Man to my fledgling slate at Reeler Releasing. Made this year as the filmmaker's thesis project at Columbia, Man was another relative festival newcomer; Joseph's story of teenage sisters bonding over the older sister's utterly unsexy tryst with an Internet suitor claimed the best director prize at the Columbia Film Festival in May and was a highlight of the Ojai Film Festival's Limelight program earlier this month. Its lean, haunting 14 minutes wrenchingly depict layers on layers of passive love, with the threats of technology, sexuality and masculinity compromising the girls' quiet codependency.

"I spent a lot of time trying not to write a film about teenagers, because so many short films are about teenagers," said Joseph, a sister herself who only half-jokingly acknowledged the traumatic experience of sharing Man with her family last spring. "But these two girls who were in this feature film that I wrote kept coming back to me. It was last December and I realized that there was no choice not do that, but I decided that I wanted to make something that was more like an honest coming-of-age that felt true to me, especially from a female perspective. Those sisters have lived with me for a while."

Man's desaturated ennui recalls a few of the acclaimed shorts of Joseph's Columbia colleagues; the overturned rustic idyll of Ian Olds' Bomb and triangulated crisis of Fellipe Gamarano Barbosa's Salt Kiss come immediately to mind (not coincidentally, Barbosa edited Man). But Man feels less alloyed than each of those films; its introspection, while not necessarily autobiographical, informs something more organic -- tragic realism as opposed to magic realism, a world where so much as a stroked finger symbolizes a watershed of compassion. It's an astonishing directing debut, the kind of fearless first effort you envy, embrace and pray for. If I don't see Joseph this winter in Park City, I'm starting a hunger strike on Geoff Gilmore's doorstep.

Seriously: In my ever-broadening, pick-your-poison festival consciousness, I never thought I'd prefer hippies to three feet of snow. But if quality's the thing, consider me converted.