Psych-ed out: The Holy Modal Rounders, subjects of the new documentary Bound to Lose (Photos: Holy Modal Rounders)

It borders on inexplicable that the Holy Modal Rounders never became a household name. The band got its start playing its one-of-a-kind folk music in the Village during the "Great Folk Scare" of the early '60s. They opened for Pink Floyd. The Rounders' single on the Easy Rider soundtrack -- "Bird Song" -- will forever be synonymous with Jack Nicholson waving his arms on the back of a motorcycle. They were the first band to use the word "psychedelic" in a song. And while Bound To Lose, the new Rounders documentary opening Friday at Anthology Film Archives (accompanied by a slew of live musical performances), takes its title from one of the band's tracks, the phrase also represents something of a mantra for their entire career.

Shot between 1999 and 2003, the film captures the band's most recent (and final) shot at the mainstream. Directors Paul Lovelace and Sam Wainwright Douglas followed Rounders co-founders Steve Weber and Peter Stampfel -- both recovered addicts, the latter now with a day job in publishing -- through a series of candid chats, shows around the East Coast and one last Western tour in a vintage station wagon.

"I really liked seeing the film," the New York-based Stampfel told The Reeler. "There were a couple of places where I really embarrassed myself, but I guess that's appropriate. There was a bunch that I'd have rather not seen in public, but, you know, that's the nature of documentaries."

Indeed, Bound to Lose features plenty of wild behavior, yelling and drug consumption. But the filmmakers also capture an unabashed candor from its aging subjects, supplying the emotional anchor that eludes many contemporary rock documentaries. "I can't think of anything with Steve or Peter or any of the Rounders where we asked them a question and they didn't want to talk about it," Lovelace said. "It was complete openness, and I think that that says a lot about them. They have nothing to hide. They're going to do it their own way, and that's just the way it is, take it or leave it. They want to find an audience and be accepted, but they're not going to be anything but the individuals that they are."

As framed by Douglas and Lovelace at home and on the road, the Rounders' trajectory is as dramatic as a line graph: The band gets its act together, and Steve Weber puts them into a nose dive. Countless almosts and could-have-beens establish a growing hope that this time the band will finally catch a break. The tension between Weber's boisterousness and Stampfel's laid-back personality peaks when Weber goes MIA just before their 40th anniversary show in Portland, Ore. In true Holy Modal Rounders fashion, though, they persevered; the show went on and the crowd was elated. Visits with Rounders loyalists are among the film's highlights, in fact, including a sit-down with Dennis Hopper and chance encounters with critics and colleagues haunting their concerts. "We would go to film these tours, and you'd never know who was going to pop up," Lovelace said. "You'd get people like Wavy Gravy, who would come out of nowhere. Or Loudon Wainwright, who just happened to be at one of their shows."

Friday's New York premiere is also the start of a week-long film and music festival welcoming local rock figures including Robert Christgau, Lenny Kaye and Stampfel himself. Anthology will also screen short films about Rounders-related bands The Fugs, The Godz and another about legendary rock critic Christgau, who also appears Bound To Lose. "Since New York is ground zero for the initial birth of the Rounders, it seems fitting that we try to bring all these different elements together," Lovelace told me. "Every night is pretty unique and has amazing stuff. The band is hard to classify, so we wanted to create this festival/party/extravaganza that's equally hard to classify."

(L-R) Holy Modal Rounders co-founders Peter Stampfel and Steve Weber

While today Steve Weber is officially retired, three of Stampfel's current bands are booked to perform playing the festivities -- and he's scheduled to sit in with just about every other group featured during the engagement. (Visit Anthology's Web site for a full program and schedule.) "I'm playing with Jeffery Lewis on Friday," he said. "We've played and recorded together, but it doesn't have an official group name. Then there's the world premiere of the End of the World Banjo Band which is basically some members of the Velocity Ramblers plus Eli Smith playing all banjo instruments, especially banjo guitar and mandolin. I've been thinking about mass banjos for several years now. I'm intrigued by the idea of how many can be played at once and still be, like, strange and radical."

Stampfel giggled when asked about the volume of work in the week ahead. "I guess that's one of the blessings of never becoming successful," he replied. "A lot of performers at a certain point in their career -- it just sort of loses its joy and the fun disappears. Thankfully we never got to a place where we had to play to huge crowds all the time, so for me performing is still fun. Now I just wish I could quit my day job."