Buckner's solo career began with Bloomed (1994), a lyrically dense suite of songs recorded in Lubbock, Texas, and produced by Lloyd Maines.

Devotion + Doubt was released in 1997, displaying a more adventurous, almost avant-garde approach to songwriting and arranging, and featuring backing from members of the band Giant Sand, as well as Maines and Marc Ribot, among others.

Its follow-up, 1998's Since, continues in this style, with an even greater emphasis on detailed production, this time featuring contributions from John McEntire, Dave Schramm, David Grubbs, Syd Straw, and others.

Although these albums garnered considerable critical approval for Buckner, they did not perform well enough for his label, and he was released from his contract with MCA Records (whom he then nicknamed "Musical Career Assassins") shortly thereafter.

[3] His 2000 album, The Hill, was released by Overcoat Recordings and features poems from Edgar Lee Masters's Spoon River Anthology, which Buckner set to music.

Buckner puts that power of observation to good use.”[10] Writing for Literary Hub, author Nina MacLaughlin said: “Cuttings from the Tangle is not the work of a road-weary musician dabbling in another form.