Wesley Harding Stace was born in Hastings, East Sussex, England in 1965. He taught himself guitar, picking out songs by John Prine, Loudon Wainwright and Bob Dylan and eventually began writing on his own as a teenager. In 1988, he cut short his Ph.D. studies at Cambridge University in favor of a career in music. An opening slot for John Hiatt attracted the attention of Demon Records who signed him and released the live It Happened One Night the same year.

In 1990, he teamed up with producer Andey Paley and members of Elvis Costello's Attractions (the association would cause Costello comparisons that would continue to haunt him) to record Here Comes the Groom for Sire. He supported the album alone in the U.S. where his spirited live shows attracted a great deal of word-of-mouth attention and strong cult following, especially in alternative and college radio. In 1991 he followed with The Name Above the Title and Why We Fight in 1992. While he received consistently good reviews, expanded on his cult following through constant touring, and finally shook (for the most part) the Elvis Costello comparisons, lack of a substantial push from Sire led to his leaving the label by the mid-90s. The self-financed John Wesley Harding's New Deal, was finished in 1996 and picked up for release by Rhino's short-lived Forward label. In 1998, he signed to Zero Hour and released Awake. In 1999, he followed with Trad Arr Jones, a collection of traditional folk songs written or arranged by Nic Jones.