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Jonathan May was born in Windsor. After taking a degree at Newcastle University he studied at Guildhall School of Music and Drama with Ellis Keeler, at the National Opera Studio, the Britten-Pears School and privately with Norman Bailey and Robert Lloyd.

Since the beginning of his freelance solo career in 1992, Jonathan's repertoire and reputation have expanded in tandem. For the Royal Opera Jonathan has sung principal roles in Il Barbieri di Seviglia, Fidelio, Madama Butterfly, Elektra, Hamlet, Lohengrin ,La Forza del Destino and La Rondine.

With Welsh National Opera, he has sung principal roles in Carmen, Billy Budd, From the House of the Dead, Un Ballo in Maschera, Parsifal and Rigoletto and latterly A Flemish Deputy and King Philippe in Don Carlos ,Orlik and Kochubey in Mazepa and Commendatore in Don Giovanni.

With his Scottish Opera  debut in 2002, Jonathan created the role of Coleridge in the world premiere of Sally Beamish's Monster and subsequently returned there in the next few seasons for principle roles in Carmen, Tosca and Madama Butterfly. For English Touring Opera, he has sung Dulcamara in L'Elisir d'amore, Colline in La Bohème, Bartolo in The Barber of Seville and Papageno in The Magic Flute; for the Garsington Festival, Peneios in Daphne; for Mid Wales Opera, Figaro in Le Nozze di Figaro, for Music Theatre Wales Eugenio in the premier of Albergha’s Letters of a Love Betrayed and for Opera Northern Ireland, Masetto in Don Giovanni.

Further afield, Jonathan sang five roles in Nigel Osbourne's The Electrification of the Soviet Union with Norway's Opera Vest and the roles of Judge/Duke/Hotel Manager in Thomas Ades Powder her Face for Opera Theatre de Metz. For Opera de Rouen Jonathan sang the Traveller in Yoshi Oida’s acclaimed production of Curlew River, conducted by David Stern, a role he reprised in 2007 at the Japan Society in New York.

From 2008 - 2010 Jonathan took time away from performing to develop a teaching practice. He is now a visiting Singing Teacher The University of St Andrews and at Shrewsbury School. He now combines the two careers as  singing teacher and performer and returning to more active performing from the 2010/11 Season.

During that season he made his debut with Grande Théâtre de Genève as Doctor in Daniel Kramer's South Bank Show award-winning production of Birtwistle's Punch and Judy and returned to Scottish Opera for Sparfucile in Rigoletto . He has since returned regularly to Scottish Opera in subsequent seasons singing Johann in Werther , Bonze in Madama Butterfly, Mandarin in Turandot,  Mayor in Jenufa, Ferrando in Il Trovatore and Doctor in Pelleas et Melisande in a new production by Sir David McVicar. 2016/17 also included  performances of Commendatore in Don Giovanni for Opera Theatre Company Dublin, sung in a new translation by Roddy Doyle.

Recent concerts include Haydn’s Creation for Stirling City Choir, Beethoven 9th Symphony for Shrewsbury Town Orchestra and Christus in St Matthew Passion for York Bach Society.

He has recorded the double role of Cadmus/Somnus in Handel's Semele, again with David Stern, released by Arion Records (PV704021/22).

Jonathan lives in Lanarkshire, Scotland and is married to the writer Janice Galloway