Formed in 1998 in Austin, Texas, Okkervil River find the middle ground between indie rock and folk-rock, placing slightly more emphasis on the former. Vocalist Will Robison Sheff and drummer Seth Warren first rubbed shoulders as high-school students in Meriden, New Hampshire, a town they eventually left to attend different colleges. The two reconvened several years later in Austin, where they put together Okkervil River with the help of bassist Zachary Thomas. The group recorded several EPs as a trio, including 2000's Stars Too Small to Use, before crossing paths with multi-instrumentalist Jonathan Meiburg at a local bar. Meiburg soon joined the band, and Okkervil River made their first big splash at the SXSW festival in March 2000.
Producer Brian Beattie caught the band's SXSW showcase and agreed to helm Okkervil River's debut album, Don't Fall in Love with Everyone You See. Warren relocated to California during the recording sessions and was replaced by drummer Mark Pedini; meanwhile, the band inked a record contract with Jagjaguwar, which released the completed Don't Fall in Love in January 2002. A second release, Down the River of Golden Dreams, followed one year later. Pedini had left the band by early 2003, however, thus leaving his former bandmates without a drummer as they prepared to return to SXSW. Travis Nelson climbed aboard as a temporary replacement and soon joined the permanent lineup, as did lap steel guitarist Howard Draper.
Already renowned in Texas, Okkervil River rose to national prominence with the release of 2005's Black Sheep Boy, followed several months later by the Black Sheep Boy Appendix EP. Both albums featured a wide crop of musicians, and the band's lineup continued to change as Scott Brackett joined on keyboards and Pat Pestorius replaced Zach Thomas on bass. Okkervil River's profile was likewise expanding, as Virgin Records reissued both Black Sheep Boy discs in Europe. Despite the international buzz, several bandmates found themselves torn between Okkervil River and Shearwater, a group originally founded in 2001 as a side project for Meiburg and Sheff. As the side project evolved into a full-fledged band, Meiburg quit Okkervil River to devote his full attention to Shearwater. Brian Cassidy was then hired, and the new lineup unveiled itself with 2007's Stage Names.