Fed up with music labels who did not return her phone calls, Williams released her debut, Dog Leap Stairs, on her own Caw Records. Co-produced by PJ Harvey associate Head, the album reportedly cost a mere 80 pounds to record (with some sources quoting as little as 75). Williams used her art school education to self-design the album cover's arresting image, setting a tradition that would be repeated on most of her subsequent releases. Dog Leap Stairs received praise for its spare arrangements and unique perspective on British folk, and Williams began to assemble a devoted following. That September, she played before an audience of 2,500 when she appeared as part of "English Originals," the Nick Drake tribute night at London's Barbican. Her performance of "Saturday Sun" was heralded as one of the highlights of the charity event; it also led to the invitation to provide backing vocals to Drake friend John Martyn's 2000 release Glasgow Walker.
Williams poured even more of her own money (3,000 pounds this time) into 2000's Little Black Numbers, which was again co-produced by Head and released by Caw. It garnered her best reviews yet from the notoriously fickle British press and would go on to secure a prestigious Mercury Music Prize nomination (an award won that year by Badly Drawn Boy). The resulting sales pulled Williams out of debt and led to a licensing arrangement with East West (a subsidiary of Warner), which re-released the album in 2001. Williams continued to branch out beyond the confines of folk when she contributed "Day by Day" to Signs, a 2000 release by the Indian-born electronica duo Badmarsh & Shri (which also appears on the CSI: Crime Scene Investigation soundtrack). Another surprising collaboration was "Demons in Cases," a 2002 single with electronica act Pedro (aka James Rutledge). Williams proceeded to record her third full-length, Old Low Light, with Head in South Wales and Newcastle. Released by East West in 2002, the cover features a family photograph of Williams and her father at the beach. By this time, Williams' backing band had solidified, comprising Laura Reid on cello, Jonny Bridgewood on bass, David Scott on guitar, and Alex Tustin on percussion. Later that year, Williams contributed "Easy and Me" to Total Lee! The Songs of Lee Hazlewood, which she then followed with three releases over the next three years: Relations (2004), Over Fly Over (2005), and the intimate Leave to Remain (2006). Throughout her career, Williams has also released a number of singles, an unusual move for a folk artist, but also a sign that she has crossover potential. And that she does; hence the frequent comparison to more pop-oriented artists like Beth Orton, Turin Brakes, and Belle & Sebastian. ~ Kathleen C. Fennessy & Andrew Leahey, Rovi