In 1969, Kirchen took Commander Cody and the Lost Planet Airmen to California and they developed a reputation as musical "outlaws" that were praised by other outlaw musicians and bands like Willie Nelson, Waylon Jennings, The Grateful Dead and the Allman Brothers Band.Kirchen's band "played a collection of rock 'n' roll, hard-core country, boogie and rockabilly sounds produced in a "high-octane mix" that made them a "happening" group in the San Francisco Bay area.

Kirchen began to develop as guitarist, vocalist, songwriter and performer. He became known for his vocal and guitar work on such songs as "Mama Hated Diesels", "Down to Seeds and Stems Again Blues" from the band's albums, Hot Licks, Cold Steel & Truckers' Favorites and Lost in the Ozone. His live performance work was captured on the 1973 album Live From Deep in the Heart of Texas, recorded at the Armadillo World Headquarters in 1973.Kirchen's Commander Cody band broke apart in 1976 and he formed a "swing orchestra" called the Moonlighters and began a decades-long collaboration with British musician Nick Lowe. Lowe produced the Moonlighters' second album Rush Hour, and Kirchen toured with Lowe and joined him in the studio from time to time. During this period Kirchen also worked on albums with Elvis Costello, Gene Vincent, and Link Wray.

Kirchen was one of the musicians that pioneered the Americana movement in the 1980s, and also with being a founding father of "twangcore," along with Dave Alvin, Wilco and Big Sandy & His Fly-Rite Boys. Kirchen's signature sound has been dubbed "dieselbilly" and incorporates elements of country, blues, rockabilly, Western swing and boogie-woogie, laced with themes of American truck driving music. Kirchen's work in the early 1970s with Commander Cody and the Lost Planet Airmen helped set the stage for the singers like Waylon Jennings and Willie Nelson and other outlaw country bands with his recordings of songs like "Seeds And Stems."Kirchen is said to have "one of the most distinctive, pure-Fender Telecaster tone guitar sounds in modern music".

Kirchen was named "The Titan of The Telecaster" by Guitar Player magazinefor his musical prowess on the Fender Telecaster guitar. He played a 1959 model with a maple fretboard and sunburst finish that he calls the "coal burner" and acquired in 1967 when he exchanged his Gibson SG with a stranger on a bus.He retired that guitar in the early 2010s in favor of a Telecaster with a wider neck.