Centered around the quivering voice and tormented but intelligently poetic songwriting of , Omaha, Nebraska band is synonymous with sad indie music. was just a teenager when he started using the moniker, and was often backed by a rotating lineup of musicians before the band gelled into an official trio of and multi-instrumentalists and . ' albums throughout the 2000s (all issued on 's indie imprint Saddle Creek) were some of their best-loved and best-performing, with releases like 2005's turning the tides of indie culture as well as cracking the Billboard charts. In 2020, after a nine-year hiatus, signed with Dead Oceans for the release of their ninth studio album, , and returned four years later with .

The roots of reach back to 1994, when at just 14 years old, was attracting regional attention as the singer and guitarist for Omaha band . A prolific songwriter, he soon amassed a number of songs that didn't gel with the rest of ' catalog, 20 of which were compiled and released in 1998 as , a solo record that doubled as 's first release under the moniker. Letting Off the Happiness followed several months later, featuring contributions from members of , , and . The album also marked the first collaboration between and producer/instrumentalist , who would play an integral role in ' success going forward.

As graduated from teenaged life to adulthood, his productivity increased. ' third release, , appeared in 1999, followed by in 2000 and Oh Holy Fools in 2001. The sound had expanded by this point, with finding room for flute, piano, and accordion in the band's music. The frontman also found room to pursue alternate projects, and he dedicated some time to before returning to the studio with in 2002. was released that summer and proved to be ' breakthrough album, with Rolling Stone deeming it one of the year's best.

released several EPs in 2004 — including Home, Vol. 4, a collaboration with 's — and rang in the following year with a pair of albums released on the same day: (whose accompanying tour produced the disc) and the electronic-slanted , both of which cracked the Top 20 in America. Hailed by some critics as the next , supported the releases with a round of festival appearances and international shows before returning to the studio once more. Recorded in L.A., Chicago, New York, Omaha, and Portland, the follow-up effort was released in April 2007, preceded by the Four Winds EP earlier that spring. Both releases featured full instrumentation — including pedal steel, Dobro, xylophone, and orchestral swells — making them some of ' most developed works up to that point.

debuted at number four in America and number 13 in the U.K., marking ' highest peak on either chart. Even so, followed such success by decamping to rural Mexico to work on his first solo effort in years. Recorded in a makeshift studio with a cast of musicians dubbed , arrived in 2008. The project soon evolved from a solo effort into a full-band affair, and returned in 2009 with , an album that included songs written and sung by several of 's bandmates. returned in 2011 with , which was recorded in Omaha and produced by and . In 2013, , which had originally been quietly issued in 2002 as a Saddle Creek online-store exclusive, was finally scheduled for its first full commercial release. This unique holiday album featured a selection of Christmas standards performed in ' trademark bittersweet style, with help from a plethora of other Saddle Creek artists including members of , , , and .

In October 2016, received the box set treatment with the aptly named Studio Albums 2000-2011, which featured remastered versions of all of the group's LPs up to 2011's . This was leading slowly to the band's emergence from their dormant state. In January 2020, announced they had signed to indie imprint Dead Oceans for the release of their ninth album, , and began sharing new songs in advance of the record's release. The album arrived in August of the same year. That October, the band released new song "Miracle of Life" as a benefit for Planned Parenthood. The track was a collaboration with , with whom had been working closely both in cameos on her tracks and with their band Better Oblivion Community Center.

In 2021, released a cover of Vic Chestnutt's "Flirted with You All My Life." The following year, the group announced they would be reissuing their first nine studio albums with new label Dead Oceans. Along with each reissue, the band released an accompanying EP with re-recorded versions of songs from the corresponding album and various unreleased cover songs. The Companion Series began with three EPs released in May 2022, one for each of the first three albums; , Letting Off the Happiness, and . Several tracks from these EPs were shared in advance of their release, including new versions of early tracks "Contrast and Compare" with guest vocals from 's , "Haligh, Haligh, A Lie, Haligh" with , and a cover of 's "St. Ides Heaven."

In 2024, ' tenth studio album, arrived, again on the Dead Oceans label. The record was full of notable collaborators including 's and members of and . ~ Andrew Leahey

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