Early on, the quartet shared stages with the Karl Hendricks Trio, Jonny Cohen's Love Machine, Crayon and The Softies. Jeff Schreckengost took over on guitar and Craig Whitman took over on drums later in 1994.
Harriet Records released the band's debut in 1994, the Our Returning Champion single, as well as the band's first full-length CD, 1995's In Action. The band produced an impressive array of songs in 1995 and 1996, releasing singles on Harriet, Hemiola Records, Rover Records, and Numeric Records over the two year period.
The group played 39 concerts over those two years, making it by far the most active period of the band's life. Boscoe's brother Paul Boscoe joined the group on vocals from 1995-1996. Drummer Tim Williams and multi-instrumentalist Eric Topolsky joined the group from 1996-1997, and guitarist Jesse Trbovich performed on guitar in 1996. 1998 saw the release of The Premise Unraveled on Portland, Oregon's Magic Marker Records. Kisswhistle's John Lancia was the group's last drummer, joining the group in 1998. The trio of Boscoe, Lancia and Parker briefly toured the Pacific Northwest in late 1998 to commemorate the release of The Premise Unraveled.
The band's final full-length effort, For You I Pine, was released in early 2000. Vehicle Flips also appeared on various compilations during their tenure, including Harriet's The Long Secret in 1995 and the Friendly Society collection in 1998, March Records Pop American Style in 1995, as well as compilations on Sing Eunuchs, ZUM and Eighty North Records.
The band called it quits soon after their performance at the 2000 CMJ festival. Boscoe went on to form The Gazetteers.