Bonnie "Prince" Billy is one of the many aliases singer and songwriter Will Oldham has used in his career in music, and it would become the most prolific, with Oldham releasing nearly all his material under the moniker from 1999 onward, the year he released the breakthrough album I See a Darkness. Whether known as Bonnie "Prince" Billy, Palace, Palace Brothers, or Palace Songs, Oldham's music has consistently used the musical framework of vintage folk and country as a vehicle for his songs imaging the joys and failings of human nature. Depending on his mood, Oldham's voice can be clear or creaky (his best vocal work often appears on interpretive albums such as 2017's Best Troubador, 2018's Wolf of the Cosmos, and 2013's What the Brothers Sang, the latter a collaboration with Dawn McCarthy), and the arrangements may be full-bodied or spectral (the evolution from Palace Brothers' 1994 album Days in the Wake to 2001's Ease Down the Road and 2004's Bonnie "Prince" Billy Sings Greatest Palace Music is instructive), but the literacy and emotional power of his songs have been constant in his recorded work, and he's grown from being an interesting outlier in alt-country to a respected figure in folk and roots music circles.
The Louisville, Kentucky native worked as an actor during the late '80s and early '90s, starring in John Sayles' 1987 mining film Matewan, 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.
Oldham was especially prolific in 2008, beginning the year with the live album Wilding in the West, an Australia-only release recorded in California during his 2007 tour. That spring, Oldham returned with Lie Down in the Light, one of his more polished efforts, which he followed that fall with Is It the Sea?, another live album recorded on his 2006 U.K. tour and released by Domino. Just a few months later in spring 2009, Beware, an ambitious effort featuring contributions from Rob Mazurek, Azita Youseffi, and the Mekons' Jon Langford, arrived, and yet another live effort, Funtown Comedown, appeared before the year was up. His next project involved the Cairo Gang, loosely a solo project for guitarist Emmett Kelly (who had often played with Oldham). The co-billing produced a record in early 2010 entitled The Wonder Show of the World, followed by the similarly themed Wolfroy Goes to Town in 2011.