Airplane Lady began informally in March of 1996. At the time, it was a collective of whoever was in the neighborhood on a Sunday afternoon and wanted to come over and play music.

After a few months, it trimmed down to a (more or less) stable lineup of five players who brought blues, jazz, funk and prog-rock influences into the mix. Shows and practices during this time consisted entirely of improvised music, which sometimes worked and sometimes did not.

The band flirted with song structures, but returned to complete improvisation, resulting in the release of the "Airplane Lady Vol. I: Recorded Improvisations" full-length CD in October of 1997. In addition, throughout this time, the quintet became a trio consisting of Kevin Toole (guitar), Matt Chandler (bass), and Rob Guernsey (drums/junk).

Favorable comparisons were made to Can, Tortoise, Miles Davis and Frank Zappa, but most found comparisons difficult to draw.

The “Airplane Lady Vol. I” CD highlights two performances which were recorded live, the way it ought to be. Tracks one and two were recorded and produced by Tim Ditchley on the “Live from Studio B” radio program on WICR, Indianapolis on June 7, 1997. Track three was recorded and produced by Airplane Lady live at Smedley’s on February 14, 1997. It is over 60 minutes in length, and the first 300 feature hand-made, hand-numbered covers.

Airplane Lady played only 22 shows, and the band ended as it began, informally, in January 1998.