Playing all of the instruments himself, Mason Jennings produced his self-titled debut at home on an analog tape machine.

Upon its 1997 release, AllMusic called the album "an amazingly realized work. A distinct sound and vocal style is evident, and there's not one clunker on this entire disc." He put a band together for a gig at Minneapolis' 400 Bar and that show turned into a weekly on a 4 month run.

By the end of 1999, the City Pages poll had Mason winning the "Pick to Click." Twenty years later, Mason is still making record and selling out shows coast to coast.