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The breakup of the influential Belleville, Illinois, roots-punk band Uncle Tupelo found Jay Farrar and Jeff Tweedy, the band's principal singer-songwriters, fronting new groups of their own. People expected less from Tweedy than they did from Farrar, who had always been regarded as the more serious artist of the two. It wasn't long, however, before Tweedy's new band Wilco outstripped Farrar's Son Volt, emerging as one of the most acclaimed and innovative bands of the new millennium.

After Farrar walked away from Uncle Tupelo in 1994, Tweedy and the remaining members of the band recorded A.M., joined by Bottle Rockets frontman and former Tupelo roadie Brian Henneman on guitar. The album found Wilco playing scruffy, country-tinged rock that suggested a cross between late-period Replacements and early-1970s Rolling Stones. Being There (Number 73, 1996), the band's lauded follow-up, saw Tweedy growing leaps and bounds as a songwriter as Wilco moved further away from the alt-country of Uncle Tupelo and more in the direction of the tuneful pop-rock of such early 1970s bands as Big Star.

Meanwhile, with Tweedy off making a second album with Golden Smog, an alt-country supergroup consisting of members of Soul Asylum and the Jayhawks, the rest of Wilco moonlighted as Courtesy Move. Besides recording several unreleased tracks of their own, the foursome provided backing on albums by singer/songwriters Steve Forbet and Jeff Black. (By this time multi-instrumentalist Bob Egan had replaced Max Johnston, who had left Wilco to play with his sister, Michell Shocked, and after that with Freakwater and the Gourds.)

In 1998 Tweedy and company accepted an invitation from British singer/songwriter Billy Bragg to travel to Dublin and set some of Woody Guthrie's unrecorded lyrics to music. The album that resulted, Mermaid Avenue (Number 90, 1998), was by turns funny, sexy, and incisive; testifying to Guthrie's irrepressible spirit and ongoing relevance, it also proved to be the best record either Bragg or Wilco had yet made. Summerteeth (Number 78, 1999), Wilco's third album, appeared the following year; more pop-leaning than its predecessors, the record was full of bright, buoyant melodies salted with Tweedy's increasingly dark, oblique lyrics. A world tour opening for R.E.M. followed, while 2000 marked the appearance of a second volume of Mermaid Avenue nearly as luminous as the first (it was largely outtakes from the first volume).

After purchasing a Chicago loft to record in, Wilco began work on its fourth album with solo artist and producer Jim O'Rourke. During the recording, there were further personnel changes in the band: Coomer and Bennett both left; Glenn Kotche, brought into the fold by O'Rourke, became the new drummer, while multi-instrumentalist Leroy Bach replaced Bob Egan. (Tweedy, O'Rourke, and Kotche also formed a side band, Loose Fur, that has released two albums on the Chicago indie label Drag City.) Yankee Hotel Foxtrot, the album that came from the tense sessions Õwhich were filmed by director Sam Jones for his 2002 documentary I Am Trying to Break Your Heart Õwas rejected by Wilco's label, Reprise, as uncommercial. While shopping for another label, Wilco streamed the album online, generating heavy fan and critical buzz and raising the album's profile. Yankee Hotel Foxtrot was finally released in 2002 by Nonesuch, a subsidiary of the Warner Music Group Õthe same corporation that owned Reprise Õand reached Number 13. Besides being named the best album of 2002 in the Village Voice's annual critics poll, Yankee Hotel Foxtrot remains, ironically enough, Wilco's best-selling album.

Their next album occasioned more shifting band positions. Bach quit Wilco after the recording of 2004's more experimental A Ghost Is Born, replaced by multi-instrumentalist Pat Sansone (the Autumn Defense); the group was also joined by the cult-favorite avant-garde guitarist Nels Cline and pianist Mikael Jorgensen. Shortly before the album's set schedule, Tweedy went into rehab for a painkiller addiction; when Ghost was issued, it went to Number Eight.. Next was Kicking Television: Live in Chicago, a double CD recorded at the Vic Theater. Wilco followed it with Sky Blue Sky (Number 4, 2007), their most scaled-back and straightforwardly rocking album in years