His talent was first recognized when he was studying divinity at Rhodes University in Grahamstown, South Africa. He later received vocal training in Vienna. While his early career was in Austria and Germany, he later settled in the United Kingdom. He has been particularly associated with Richard Wagner's operas, including the title role of The Flying Dutchman, which he recorded with the Chicago Symphony under Sir Georg Solti, and the role of Wotan in the Ring Cycle which he sang in the Sadler's Wells Opera/English National Opera production under Reginald Goodall. In these performances he appeared alongside Rita Hunter as Brünnhilde and Alberto Remedios as Siegfried. The recordings made with these artists, taken from live performances at the London Coliseum, are often regarded as constituting a classic audio Ring cycle. Another major Wagnerian role which he sang in many opera houses was Hans Sachs in Die Meistersinger von Nürnberg, which he recorded in German with the Vienna Philharmonic under Solti on Decca/London, and in English from the ENO under Goodall on Chandos. His performances of the role at the Metropolitan Opera in New York also drew sterling critical and popular praise. Other memorable performances include the role of Barak in the 1981 WNO production of Die Frau ohne Schatten, and the Father in Engelbert Humperdinck's opera Hansel and Gretel. Also in the 1980s, he was heard in the role of Dr. Engel in the first recording of the complete score of the operetta The Student Prince, by Sigmund Romberg and Dorothy Donnelly. He has also performed with the Royal Opera House, Covent Garden and in many other opera houses around the world. He made his Glyndebourne debut in Berg's Lulu when he was sixty-five and celebrated his seventy-fifth birthday by singing the role of Sarastro in Mozart's Die Zauberflöte at the Eliza R. Snow Performing Arts Center in Rexburg, Idaho. Bailey has appeared on BBC television and radio almost 100 times, including both performances and interviews. He was a "castaway" on an October 1976 edition of Desert Island Discs, and was pictured, alongside Patricia Johnson, on the cover of the 3-9 December 1977 edition of the Radio Times He was appointed a Commander of the Order of the British Empire in the 1977 New Year Honours.
