Walker was born in Upstate New York and moved to Greenwich Village in New York City in the late 1960s. He recorded two albums on Vanguard Records as part of a folk-rock band called Circus Maximus. After they disbanded in 1968, he signed to Atco Records but saw little commercial success.
In 1970, he moved to Austin, Texas, where he found his true musical home. Along with Waylon Jeninngs, Willie Nelson, Johnny Cash and others, he spearheaded the "outlaw" country music movement. It was also during this time that The Nitty Gritty Band had a Top 10 hit with their version of his song, "Mr. Bojangles."
Walker never had a huge hit on his own but did record a number of gold albums with his backing group, The Lost Gonzo Band. He named himself "The Gypsy Songman" and has remained a steady recording and touring act with a very loyal cult following.