[4] They have appeared on the talk show Late Night with Conan O'Brien and have performed with acts such as The Decemberists, The New Pornographers, The National, and Lou Reed.

Okkervil River's founding members became friends at Kimball Union Academy in Meriden, New Hampshire, and after parting ways for college moved to Austin, Texas to live together and start a band.

One year later the band traveled to San Francisco and reunited with Warren to record their third album at Tiny Telephone Studios with engineer Scott Solter at the console.

In 2003, Pedini left the band to pursue his graphic design work, leaving Okkervil River without a drummer for that year's SXSW.

They invited Travis Nelsen, fresh off a tour filling in on drums for sister labelmates Secretly Canadian's Swearing at Motorists, to perform with them.

As a result of the album's critical success, Okkervil River followed up with an EP entitled Black Sheep Boy Appendix on November 22, 2005.

This was the first recording with Draper, horn and keyboardist Scott Brackett, guitarist Brian Cassidy, and touring bassist Pat Pestorius, who eventually replaced Zach Thomas in the band.

[14] These recordings, along with the upcoming appendix, are the first to feature contributions from new touring keyboardist, Justin Sherburn, who joined the band in November 2007.

[16] To promote the album, the band went on tour in 2011 with Titus Andronicus, Julianna Barwick, Future Islands and NewVillager.

[17] In September 2013 Okkervil River released their seventh album, The Silver Gymnasium, the content of which is inspired by Sheff's childhood and hometown.

The album features a new backing band and sonic direction, including contributions from Marissa Nadler, Jonathan Meiburg and members of the classical group yMusic.

[19] The content of the album is largely based on Will Sheff's life during the 2013–2015 period after the release of The Silver Gymnasium, during which many members of the band left and his grandfather died.

Will Sheff produced the album while Shawn Everett (Perfume Genius, Alabama Shakes, The War on Drugs) assumed mixing responsibilities.

The band's 2006 release, Palo Santo (sans Sheff's vocals, but including his musical input), has seen Meiburg receive great critical acclaim.

On April 20, 2010, former 13th Floor Elevators singer-guitarist Roky Erickson released the album True Love Cast Out All Evil, produced by Will Sheff and backed by Okkervil River.