[4] Jennings produced his self-titled debut album in 1997 on an analog four-track in the living room of a rented home, playing all instruments himself.

[5] In October 1998, joined by drummer Chris Stock and bassist Robert Skoro, he began a weekly gig at the 400 Bar as the Mason Jennings Band.

In April 1999, six months after forming, The Mason Jennings Band was voted by the 1999 "Picked to Click Poll" conducted by the Minneapolis-St. Paul newspaper, City Pages.

Mason began touring nationally and expanded the depth of his sound by inviting saxophonist Chris Thomson to play with them occasionally and replacing Stock with Brazilian jazz drummer Edgar Olivera.

On June 17, 2005, Jennings signed with Glacial Pace, a subsidiary of Sony's Epic Records headed by Modest Mouse frontman Isaac Brock.

Jennings had long avoided the major labels, citing desires to maintain creative control and dodge big-label politics.

Jennings recorded his sixth album, Boneclouds, at Pachyderm Studio in Cannon Falls, Minnesota, with producer Noah Georgeson.

Jennings sang two Bob Dylan songs which Christian Bale lip-synched in the movie "I'm Not There" (released in November 2007 in the U.S.): "The Times They Are a-Changin'" and "The Lonesome Death of Hattie Carroll."

Jennings announced at the Elemental Experience Music & Arts Festival in San Diego, California on May 2, 2009, that he would be releasing a new album (later entitled Blood of Man) in summer 2009.

[7][8] Jennings has been honored with a star on the outside mural of the Minneapolis nightclub First Avenue,[9] recognizing performers that have played sold-out shows or have otherwise demonstrated a major contribution to the culture at the iconic venue.