Bailey was born in Sheffield, England. A third generation musician, he began playing the guitar at the age of ten, going on to study with John Duarte among others. As an adult he found work as a guitarist and session musician in clubs, radio, dance hall bands, and so on, playing with many performers including Gracie Fields, Bob Monkhouse and Kathy Kirby, and on television programs such as 'Opportunity Knocks'. Bailey was also part of a Sheffield based trio founded in 1963 with Tony Oxley and Gavin Bryars called 'Joseph Holbrooke' (named after the composer, whose work they never actually played). Although originally performing relatively 'conventional' jazz this group became increasingly free in direction.
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