Siebel was born in 1937 in Buffalo, NY. Inspired by Hank Williams and Hank Snow, he taught himself to play guitar while in his teens. By the early '60s, after serving in the military, he began playing folk clubs, eventually moving to Greenwich Village, where he found support in the coffeehouse circuit. In 1969, a collections of demos he made with David Bromberg caught the attention of Elektra Records owner Jac Holzman, who offered a him a modest recording deal (reportedly he was only given enough money to finance four three-hour recording sessions). The resulting album, Woodsmoke and Oranges, was met with critical praise from the media, including Rolling Stone magazine. Despite the attention, the album and its equally praised follow-up, Jack-Knife Gypsy, sold disappointingly little. Aside from a live album released in 1981, Live at McCabes, Siebel hasn't released an album since.