While alive, Van Zandt was labeled as a cult musician: though he had a small and devoted fanbase, he never had a successful album or single, and even had difficulty keeping his recordings in print. In 1983, Willie Nelson and Merle Haggard covered his song "Pancho and Lefty", scoring a number one hit on the Billboard country music charts. Despite achievements like these, the bulk of his life was spent touring various dive bars, often living in cheap motel rooms, backwoods cabins and on friends' couches. Van Zandt was notorious for his drug addictions, alcoholism, and his tendency to tell tall tales. He suffered from manic depression, and attempts to treat it with insulin shock therapy erased much of his long-term memory.
Van Zandt died on New Years Day 1997 from health problems stemming from years of substance abuse. The 2000s saw a resurgence of interest in Van Zandt. During the decade, two books, a documentary film and a number of magazine articles about the singer were created. Van Zandt's music has been covered by such notable and varied musicians as Bob Dylan, Lyle Lovett, Norah Jones, Steve Earle and The Meat Puppets.
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