The Disappointments formed in the kitchen of a small house in Chicago's Humbolt Park neighborhood on a horrendously cold, sub zero degree day in January 1996.

It was one of those Chicago winter weekends that was so cold there was nothing else to do but play rock and roll. The bars were still closed. And no beer was on hand.

The house was home to guitarist Surf Zombie (AKA Dave Martinez of the late, great surf instrumental orchestra the Landsharks.) The first lineup of the yet unnamed Disappointments was Dave Martinez on guitar and vocals, his friend Daniel James on bass, Glenn Wall (the Housekeepers) on guitar and vocals and Martinez's then roommate Steve Uppling (Rockin' Billy and the Wild Coyotes) on drums.

The Disappointments made their debut a few months later at the now defunct Chicago bar Zak's, and soon played a full set at the punk club Circuits, opening a show for Rockin' Billy and the Wild Coyotes before a sparse crowd. Another show at Circuits soon followed with drummer Steve Gauge (the Nobodys, the Young Fathers) on drums.

A year or so and several dive bar gigs later Martinez bid farewell to the group when he married (the band played at his wedding reception) and for a while the group gigged as a 3-piece outfit with various drummers at Chicago bars like Phyliss' Musical Inn and the Gallery Cabaret. At this time they also played a show or two not as the Disappointments but as the Floozies. Then, in late 1996, Wall, James and Gauge started recording in a small studio in Chicago's West Roger's Park area.

They recorded, mixed and mastered six songs, including "Lisa's Lies" and "Waiting to See You Smile", along with another song which aired on a local talent radio shows. The group continued to play sporadic gigs between recording sessions and fighting amongst each other.

In April of 1997, Lou Hallwas (the Differents) joined Wall and James, on guitar, while at the same time Gauge (drums) left and was replaced by Sean O'Malley (the Shakes.) This lineup made its debut with Hallwas reading the chords and words off of paper sheets during the band's first show.

The band re-entered the studio for more recording, which approximately a year later became the CD "Tall, Dark and Hasbeen." While recording was being completed, James (bass) left and was eventually replaced by Chicago area band veteran Mike Keuchenberg (The VUs, Full Grown Men, the Offbeats) leaving Wall as the only original member of the group.

Tall, Dark and Hasbeen was released to the rock pop underground in August of 1998. Although it's ill- fated "record release show" was attended by few, the CD's mix of inspired midwest power pop, colorful 60s and 70s influenced guitar rock and a touch of urgent 90s alternative country received good reviews and airplay on international indy rock radio while the band played more shows in Chicago clubs like Morseland and seedy, smoky and dark corner bars.

In the fall of 1998, Sean O'Malley left. The band recorded two songs on New Year's Day, 1999, with drummer Brad Elvis (the Elvis Brothers, Big Hello) at Chicago's Kingsize Studio. More recording followed at Chicago's Uberstudio throughout 1999, a year in which the band played few shows, mostly with stand-in drummers.

Midwest Coast (Undefeated Records) was released in the fall of 2000 to good reviews. At the same time the Disappointments had extended its number of indy label record distributors and was awaiting the release of one of its songs on a compilation of Illinois Power Pop bands by Sweden's Power Pop label Yesterday Girl Records and also recording demos of new material.

Contrary to popular belief, with the exception of a few shows here and there, the Disappointments have always been a four-piece band. They have often been referred to as a three-piece group as they were between bassists at the photo session for their first CD, and between drummers at the photo session for their second.