Like everyone else he knew who’d heard it, Drag City publicist Zach Cowie was obsessed with Gary Higgins’s 1973 LP Red Hash–an obscure psych-folk masterpiece in a class with hippie-era rarities like Skip Spence’s Oar, Linda Perhacs’s Parallelograms, and Vashti Bunyan’s Just Another Diamond Day. In 2003 his friend Ben Chasny, leader of the band Six Organs of Admittance and guitarist for Comets on Fire, had given him a copy of the album, and Cowie spent most of the next two years tracking Higgins down. In late July, Drag City reissued Red Hash to glowing reviews in publications ranging from Vice magazine to the New York Times, and the first pressing of 5,000 copies quickly sold out.

Best of Chicago voting is live now. Vote for your favorites »

Red Hash is still Higgins’s only release, and his career as a professional musician was essentially over even before it came out–he was serving time in a maximum-security prison on drug charges. A native of rural Sharon, Connecticut, he formed his first band, Random Concept, in 1963. Three years later the group–which included singer Simeon Coxe, who’d go on to form the legendary Silver Apples–moved to New York City and took up residence at the Hotel Albert, alongside lodgers like Tiny Tim, the Lovin’ Spoonful, and the Blues Magoos. Random Concept got work, but their schedule was grueling–they often played six sets a night–and they were unused to the demands and excesses of the big city. “We were kinda homesick,” says Higgins. “So we decided to go back to our roots and regroup. It probably wasn’t the best business decision, but it’s where all our heads were at.”

Higgins and his friends were “hippies living in the country,” as he puts it–hardly dangerous radicals. But because they were in small-town America during the Vietnam era, when Nixon had just declared his war on drugs, they attracted a lot of unwanted attention from police. “If you didn’t have a butch haircut and weren’t headed for the army, then there was something wrong with you,” says Cardillo. They regularly bought and smoked marijuana (“I even inhaled,” jokes Higgins), and when a sting operation in October 1972 failed to catch the local dealers prosecutors were after, Higgins and Cardillo–who knew one of the targets–were next in line. Both were convicted of selling hashish. “It certainly shocked us,” says Higgins. “But it brought forth an urgency in getting my music down on tape, because I didn’t know if I’d ever get another chance.”

In 2003, when Ben Chasny introduced Zach Cowie to Red Hash, he’d been hung up on it for three years. Cowie, a Naperville native and former Touch and Go staffer, was working for Sub Pop in Seattle, but in spring 2004 he returned to Chicago and started at Drag City. He ran nationwide online people searches, trying to contact every Gary Higgins he could find. In October of that year Chasny recorded a cover of “Thicker Than a Smokey,” a song from Red Hash, for Six Organs’ School of the Flower, hoping Higgins would learn about it and get in touch.