Their full-length debut album Old Liquidator was released in 1995, and the Minus 5's lineup consisted of McCaughey, Buck, and Jon Auer and Ken Stringfellow of The Posies. After releasing Old Liquidator on East Side Digital, the group reconvened in late 1996 to record their Hollywood Records debut, The Lonesome Death of Buck McCoy, released the following spring. Also in 1996, McCaughey's 1989 solo album My Chartreuse Opinion was reissued by Hollywood as a Minus 5 album.
In 1999, the group accepted an invitation to participate in a tribute album to Moby Grape co-founder Skip Spence, who was terminally ill with cancer, for the purpose of raising funds to assist with medical expenses.
In 2001, the Minus Five and the Young Fresh Fellows, another McCaughey project, released a split double album, Let the War Against Music Begin/Because We Hate You; the "Let the War Against Music Begin" half was the Minus 5 submission.
After a change of guard at Hollywood Records, the Minus 5 found themselves releasing music via independent channels, with the Return to Sender label releasing a collection of outtakes from Let the War Against Music Begin called I Don't Know Who I Am before McCaughey signed the band to the Yep Roc label for his collaboration with Wilco, Down With Wilco. Yep Roc later issued an EP dominated by Down With Wilco outtakes, At the Organ, and reissued In Rock, a collection of tunes McCaughey recorded in a single day in 2000.
In 2002, the band contributed a track, "Girl I Never Met" to Rami Jaffee, Pete Yorn, and Marc Dauer's Trampoline Records release: Trampoline Records Volume I.
The band's seventh album, self-titled (but known as The Gun Album), was released early 2006, and features, along the regular line-up, guest appearances by Wilco, Kelly Hogan and The Decemberists' singer/songwriter Colin Meloy, among others.
In 2012 The Minus 5 recorded a version of the 1976 hit single by the Sutherland Brothers and Quiver "Arms of Mary" for a fund raising cd titled "Super Hits Of The Seventies" for radio station WFMU. The band played at SXSW in 2013.
^Being a compilation of cover versions of the songs from the solo album by Moby Grape co-founder Skip Spence, Oar, originally released by Columbia Records in 1969. Minus 5 performs their thirteen-minute version of Spence's "Doodle".