When I heard the music of the Holy Modal Rounders in the later 60s, I loved it. I didn't know the source material then, but it was basically Harry Smith's "Anthology of American Folk Music" performed while under the influence of LSD and Methamphetamine, with a wonderfully weird and funny sensibility. The original Rounders where just Steve Weber and Peter Stampfel. Later Stampfel and Weber were in the original Fugs. And even later the Rounders went electric with a bigger band and, for a few years, had the actor and playwright, Sam Shepard, as their drummer. The Rounders and The Fugs were the anarchic humorous side of the drug rattled New York folk scene.
The 2007 documentary "The Holy Modal Rounders: Bound To Lose" finally made it to Netflix and the bureau chief and Madame Le Chef watched it. It's well worth looking at if you're curious about the Rounders and that (in retrospect) amazing epoch, but the central insight that I got from it is that wretched excess can be a great aide to creativity in the short run but is a very bad plan for survival in the long run. Stampfel was saved by the love of a good woman (how Victorian) in the person of Betsy Wollheim, his second wife. He gave up the LSD and the Meth. Weber transitioned into full on alcoholism and is basically a rolling disaster, although still very talented. Antonia, Stampfel's first wife and the cowriter of a lot of his early songs, stuck with Meth for decades more and the neurological damage she did to herself is painful to watch in the film.
Although most of the Rounders songs are lively and funny, a few have a haunting quality and the exemplar of that is "Bound to Lose'. It works well in the title of the film, since the Rounders were never able to financially capitalize on their wild talent, but it's also just a damn good song.