Bailey began his musical career in a skiffle band in 1958, and later joined folk supergroup the Three City Four featuring Leon Rosselson, as a replacement for Martin Carthy.

On 23 August 2006, he returned his MBE insignia in protest at the British government's foreign policy with regard to Lebanon and the Palestinian territories.

He contributed vocals to Chumbawamba's 2008 album The Boy Bands Have Won, on the track "Word Bomber", a song about the London suicide attacks in 2005.

[8] The album contained songs written by Si Kahn, Bob Dylan, Tom Waits, John Tams, Robb Johnson and others.

[9] A posthumous album was released in late 2020 entitled Roy Bailey Remembered, featuring performances from Nancy Kerr and James Fagan, The Wilsons and The Spooky Men's Chorale.