Drawing on influences like Gram Parsons, the Louvin Brothers, Tim Hardin, and Nashville Skyline-era Bob Dylan, the Jayhawks quickly became a local favorite, honing their sound in Twin Cities clubs before releasing their eponymous debut in 1986. Issued in a pressing of just a few thousand copies, the album was well received by those who heard it; a major recording deal did not follow, however, so the bandmembers continued to polish their craft live, with more and more of their songs bearing writing credits belonging to both Olson and Louris. In October 1988, after a lineup change that saw the departure of Rogers (who joined the Cows) followed by the addition of drummer Thad Spencer, Louris was nearly killed in an auto accident, and the Jayhawks went on hiatus. At much the same time, however, executives at the Minneapolis independent label Twin/Tone decided to issue the demos the group had been stockpiling over the past few years, and after some overdubbing and remixing, Blue Earth appeared in 1989. Richer in sound and more complex in its themes and concerns, the record's release brought the group considerable attention, and also brought Louris back into the fold. After another drummer switch (Spencer for Ken Callahan), the band hit the road for a national tour.

The Jayhawks were signed to major-label American Records after producer George Drakoulias heard Blue Earth playing in the background during a phone call to Twin/Tone's offices. With Drakoulias in the producer's seat, the band recorded its breakthrough album, Hollywood Town Hall, in 1991; a mainstay of critics' annual "best-of" lists, the album generated the alternative radio hits "Waiting for the Sun," "Take Me with You (When You Go)," and "Settled Down Like Rain." After a tour that saw the permanent addition of Minneapolis pianist Karen Grotberg, the individual bandmembers guested on albums from Counting Crows, Soul Asylum, Maria McKee, Joe Henry, and others. Before recording the fourth Jayhawks album, Callahan departed, and was replaced by session drummer Don Heffington. The resulting record, 1995's Tomorrow the Green Grass, is a beautiful collection of songs led off by the elegiac single "Blue," the recipient of significant airplay. A tour followed, but after some months on the road, Olson announced he was quitting the band.

In 1997, the Jayhawks -- now consisting of Louris, Perlman, Grotberg, and drummer Tim O'Reagan -- released the album Sound of Lies. Grotberg left the band in early 2000, and was replaced by ex-DAG keyboardist Jen Gunderman for the band's sixth album, Smile. A move to a new label (Lost Highway) in 2002 brought about more changes in the band's ever evolving lineup, leaving Louris, Perlman, and O'Reagan (assisted by newcomer Stephen McCarthy on guitar) to craft 2003's rootsier Rainy Day Music. After that, the band ceased operating under the moniker, though Olson and Louris toured together in 2005 and 2006 billed as "From the Jayhawks: An Evening with Mark Olson and Gary Louris, Together Again," eventually releasing an album together in 2009 called Ready for the Flood. That same year, the band released Music from the North Country: The Jayhawks Anthology, and a reissue of 1986's Bunkhouse Album appeared soon after.

During the summer of 2009, the Jayhawks reunited for two festival dates in Spain. The success of both shows encouraged the bandmates to bring the reunion back to America, where they holed themselves up in several locations (Louris' apartment in Minneapolis, Olson's home in Joshua Tree, a cabin in northern Minnesota) to write new material. Most of those new songs made their way onto 2011's Mockingbird Time, the band's first release in nearly ten years.