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Windsor did 2 years teacher training in Bangor then taught History and English in the Elephant and Castle in London where he met Lynne, his future wife, who was a nurse, in the Welsh Club. By the time he was 32 they had 2 children and were living in Leek, in Staffordshire. He had always been keen on amateur dramatics and Lynne persuaded him to try the theatre. The casting director of the Royal Court Theatre got him into Cheltenham Reportary at £10 a week which started his show business career.