It was almost 40 years ago that guitarist Steve Weber and fiddler Peter Stampfel, who make up the core of the Holy Modal Rounders, collided from a shared love of American roots music and altered states of reality. With their bizarre original compositions and absurd versions of traditional folk songs, they were standards in the Village folk circuit. After several landmark albums in the 60s and 70s, the Rounders played with the likes of Ike and Tina Turner, Pink Floyd and Velvet Underground, but were most popularly recognized for their contribution to the Easy Rider soundtrack. While Peter Stampfel settled down and raised a family in New York City, Steve Weber and the rest of the band relocated to Oregon in the early 80s. Twenty years of hard living later, Weber returned to the east coast to recuperate at his mother’s farmhouse, and the two reconnected. After countless lineup changes, drug addictions, breakups and breakdowns, the HMR were once again recording (1999’s critically acclaimed comeback album “Too Much Fun”) and performing unforgettable shows.

For three years filmmakers Sam Douglas and Paul Lovelace explored the fraternal love/hate relationship of Stampfel and Weber as it unfolded onstage, backstage, and in their private lives. And as they prepared for their 40th anniversary gig in Portland, the ups and downs and unpredictability of their history take yet another turn. Featuring interviews with journalists Robert Christgau and Byron Coley, former band member Sam Shepard, Dennis Hopper, fellow musicians and fans Peter Tork, John Sebastian, Dave Van Ronk, Ira Kaplan of Yo La Tengo, and with appearances by Loudon Wainwright III and Barry Melton of Country Joe and the Fish fame, Bound to Lose is a testament to The Holy Modal Rounders as true American underground music originals and examines the marriage between creativity and addiction, the ups and downs of a long career in music, and ultimately the durability of a friendship.