An earlier version of "The Old School Off The Bright" was originally featured on a promotional EP titled Fabled Barney and The Population given out at the band's Hometown Throwdown in 2002.

The track "I want My City Back" is a lament about the loss of The Rathskeller, commonly called The Rat, the club in Boston where the Bosstones got their start.

On March 3, 2002, A Jackknife to a Swan was announced for release in July; it was revealed that the band had signed to SideOneDummy Records.

[7] In November and December 2002, the group went on a headlining US tour, with support from Bigwig, Slick Shoes and Simple Plan.

The following month, they embarked on a brief east coast tour with Voodoo Glow Skulls, the Pietasters, and Catch 22.