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The formation of Um followed the organic pattern common to many jazz ensembles, unfolding gradually across multiple years before its roster reached completion. Originating in 1992, the project began as a vehicle for trombonist Hal Crook (Phil Woods, Tony D'Aveno) to introduce his own compositions written for the Trom-o-Tizer, a digital effects processor that layered harmonies onto his trombone lines and ensured audibility above the rhythm section. The initial trio, completed by drummer Bob Gullotti (the Fringe, Surrender to the Air), secured a weekly engagement in their hometown of Providence, RI.

Guitarist Rick Peckham eventually supplanted the regular bassist. Audiences and fellow players routinely dropped in to hear the band, whose originals frequently suggested conventional be-bop refracted through a chaos filter. On occasions when Crook performed elsewhere, bassist Dave Zinno (one of Crook's former students) would substitute. The pair ultimately shared the bandstand one evening, after which Zinno joined permanently and the group expanded to a quartet. Its music routinely traversed the territory between free jazz, hard grooves, bebop, and swing.

A succession of visiting musicians, among them George Garzone, Bob Brookmeyer, and Mick Goodrick, sat in over the ensuing period. Organist John Medeski (Medeski, Martin, and Wood), who had previously worked with Gullotti in Trey Anastasio's Surrender to the Air project, later appeared in town. Following several such appearances, the ensemble elected to document a handful of performances. The resulting recordings, made on May 11 and 12, 1999, at the group's home base Club AS220 in Providence, were issued as the album Stray Dog on Ropeadope Records in fall 2001, the in-house label associated with the extended Medeski, Martin, and Wood circle. The musicians, typically appearing without Medeski owing to his numerous other commitments, continue their weekly performances in Providence.