After his stints performing as Palace, Palace Songs, Palace Brothers, and under his own name throughout the '90s, by the end of the decade Will Oldham seemed to finally settle on the Bonnie "Prince" Billy moniker as the main outlet for his work. Regardless of the name he used to release his music or the musicians supporting him, Oldham's style remained largely the same, pitting shambling and often sparse music against his creaky, world-weary voice and literate lyrics. The Louisville, KY, native worked as an actor during the late '80s and early '90s, starring in John Sayles' 1987 mining film Matewan and appearing in the 1989 TV movie Everybody's Baby: The Rescue of Jessica McClure and the 1991 big-screen film Thousand Pieces of Gold.
Oldham debuted as a musician in 1992 with the Drag City single Ohio River Boat Song, which he released as Palace Songs; his debut album, There Is No-One What Will Take Care of You, arrived the following year as a Palace Brothers offering. By 1995's Viva Last Blues he was beginning to work as Palace Music, a name that stuck until 1997's Joya, which Oldham released under his own name. However, with 1998's Black Dissimulation and the following year's I See a Darkness, the Bonnie "Prince" Billy name seemed to stick, for the most part: aside from the soundtrack Ode Music and Guarapero: Lost Blues 2, the majority of Oldham's work from then on was credited to Bonnie "Prince" Billy. Ease Down the Road arrived in early 2001, featuring collaborators David Pajo, Catherine Irwin, Mike Fellows, and Harmony Korine. Master and Everyone appeared two years later. In 2004 came the release of a rather surprising project for Oldham -- Bonnie "Prince" Billy Sings Greatest Palace Music, in which his usual collaborators were joined by a band of Nashville session musicians for a set of polished re-recordings of songs from his back catalog.
Bonnie "Prince" Billy's next project found him collaborating with guitarist Matt Sweeney (who had previously worked with Chavez and Zwan, as well as playing banjo on Ease Down the Road) for the evocative January 2005 release Superwolf. Reflective, bittersweet, and achingly melodic, it was praised as one of the year's first truly strong albums. Oldham and Sweeney followed up Superwolf that July with an extended single for I Gave You featuring two non-album tracks. Sweeney was also on hand for the live album Summer in the Southeast, issued by Sea Note in November 2005. Bonnie "Prince" Billy and Sweeney were joined by a full band for the shows. ~ Heather Phares & Tom Erlewine, All Music Guide