New Riders of the Purple Sage, live at Fillmore East, April 29, 1971. Click here for the setlist, or to download the whole thing as MP3s

Dilettantes dabbling in the genre of country music have always had a hard time, from hippies like Gram Parsons to his modern day alt-country hipster inheritors. There’s almost always an inevitable anxiety over class privileges and the fetishization of working class experience by cultural elites. That combines with the classic rural versus urban divide and adds up to an awkward night sitting in a bar in Silver Lake listening to delicate, good-looking dudes in fancy vintage Western shirts singing about CB radios and old pickup trucks. It’s airless tribute at best, unaware cowboy drag at worst.

John “Marmaduke” Dawson was the lead singer and main songwriter for The New Riders of the Purple Sage, the best of the hippie country bands that emerged from the West Coast psychedelic rock and rustic folk scenes, and one of the only bands — along with Commander Cody, Doug Sahm and Asleep At The Wheel [thanks for reminding me, Michael!] — that managed to merge roper with doper without apologies to either camp. He died on Tuesday in San Miguel de Allende, Mexico, where he’d been teaching English as part of the city’s established community of American expatriates. He was 64, and stomach cancer was the culprit.

Travel to Mexico is the subject of one of the New Riders best-known songs, “Henry.” Marmaduke often dedicated live performances of the song to anyone in the audience who “smuggles dope for a living,” and given that most of the New Riders best shows were during the early ’70s opening for the Grateful Dead, there were no doubt plenty of audience members who appreciated such recognition.

“Henry” is about the titular drug runner on his way down to Acapulco to find out why all the marijuana has stopped flowing to the United States. After navigating a series of twisty mountain roads, he finds his supplier’s farm and proceeds to get thoroughly obliterated on freshly trimmed crops. The song is about the drive back, as told from the perspective of an unnamed passenger, who is continually beseeching the seriously faded Henry to keep the brakes on as they careen through the mountain passes.

It’s a song that, like so many New Riders tunes, conveys a distinctly hippie experience using the language of country music. The band was an outgrowth of Jerry Garcia’s pre-Dead unit, the wacky bluegrass band Mother McCree’s Uptown Jug Champions. The Dead did plenty of country-leaning material, but Garcia still wanted an outlet for his pedal steel licks, and thus the New Riders of the Purple Sage came to be.