Allen's musical career spans several albums in the Texas country and outlaw country genres, and his visual art includes painting, conceptual art, performance, and sculpture, with a number of notable bronze sculptures installed publicly in various cities throughout the United States.

Other artists who have recorded Allen's songs include Guy Clark, Little Feat, David Byrne, Doug Sahm, Ricky Nelson, and Lucinda Williams.

[2] Rolling Stone magazine describes his catalog, reaching back to Juarez as "..uniformly eccentric and uncompromising, savage and beautiful, literate and guttural.

Kansas City, Missouri is home to both his controversial public sculpture Modern Communication[9] as well as The Belger Collection[10][11] which features Terry Allen as one of their seven "core artists".

[1] His 1983 album Bloodlines includes one of his better-known songs, "Gimme a Ride to Heaven Boy", the tale of a driver who picks up a hitchhiker on the road one night who claims to be Jesus Christ.

Over the following decade (1985-1995), Allen released a series of albums with avant-garde elements, as companions to visual art, theatrical and musical projects – Pedal Steal, Amerasia and Chippy (the latter also the soundtrack of a stage play in collaboration with Joe Ely, Butch Hancock, Robert Earl Keen and Wayne Hancock).

In 1996, he released the country album Human Remains, which features guests including David Byrne, Joe Ely, Charlie and Will Sexton and Lucinda Williams.

Allen's 2013 album Bottom of the World features "Queenie's Song", inspired by the death of his dog and co-written with Guy Clark.