[1] Bailey abandoned conventional performance techniques found in jazz, exploring atonality, noise, and whatever unusual sounds he could produce with the guitar.

In addition to solo work, Bailey collaborated frequently with other musicians and recorded with collectives such as Spontaneous Music Ensemble and Company.

[2] As an adult he worked as a guitarist and session musician in clubs, radio, and dance hall bands, playing with Morecambe and Wise, Gracie Fields, Bob Monkhouse, Kathy Kirby, and on the television program Opportunity Knocks.

[2] At the Little Theatre Club run by drummer John Stevens, he met like-minded musicians such as saxophonist Evan Parker, trumpeter Kenny Wheeler, and double bassist Dave Holland, with whom he formed the Spontaneous Music Ensemble.

Bailey formed the Music Improvisation Company with Parker, percussionist Jamie Muir, and Hugh Davies on homemade electronics.

He was a member of the Jazz Composer's Orchestra and formed the trio Iskra 1903 with double bassist Barry Guy and trombonist Paul Rutherford[2] that was named after a newspaper published by Russian revolutionary Vladimir Lenin.

[7] In 1976, Bailey started the collaborative project Company,[2] which at various times included Han Bennink, Steve Beresford, Anthony Braxton, Buckethead, Eugene Chadbourne, Lol Coxhill, Johnny Dyani, Fred Frith, Tristan Honsinger, Henry Kaiser, Steve Lacy, Keshavan Maslak, Misha Mengelberg, Wadada Leo Smith, John Zorn and many other musicians.

[10] Bailey argued that his approach to music-making was actually far more orthodox than that of performers such as Keith Rowe of the improvising collective AMM, who treats the guitar purely as a "sound source" rather than as a musical instrument.

This led to work with collaborators such as Pat Metheny, John Zorn, Lee Konitz, David Sylvian, Cyro Baptista, Cecil Taylor, Keiji Haino, tap dancer Will Gaines, Drum 'n' Bass DJ Ninj, Susie Ibarra, Thurston Moore of Sonic Youth and the Japanese noise rock group Ruins.

"[12] Mirakle, a 1999 recording released in 2000, shows Bailey moving into the free funk genre, performing with bassist Jamaaladeen Tacuma and drummer Grant Calvin Weston.

Characteristically, he refused invasive surgery to treat his condition, instead being more "interested in finding ways to work around"[citation needed] this limitation.