Simon grew up in Suffolk and was head chorister at St Edmundsbury Cathedral. Much later he enjoyed a choral scholarship at St Johns College Cambridge, whilst studying for his degree in Theology. During this period he cut his teeth as a soloist at various colleges, and in oratorio engagements at cathedrals and churches throughout the country. Upon graduating he worked as personal assistant to composer John Rutter for three years, after which he took up a scholarship at the Royal Academy of Music, where he studied with Ashley Stafford.
Simon has given recitals singing a wide repertoire including English and French song, Lieder, and operatic arias, together with substantial dramatic works such as Brittens Abraham and Isaac and The Journey of the Magi. During 2003 he premiered solos in John Taveners epic seven hour The Veil of the Temple, which called for him to sing a 15 minute unaccompanied gospel at 5am! He did so again at the Lincoln Center, New York (the US premiere) and at the BBC Proms. This version has since been released as a CD on RCA. He has appeared as a soloist with The Monteverdi Choir conducted by Sir John Eliot Gardiner in the USA in Haydn masses, and in Europe and the Far East in Purcells Dido and Aeneas; for Polyphony, in Hyperion recordings of James Macmillans Seven Last Words, conducted by Stephen Layton; at the Three Choirs Festival under Hickox; and for Laurence Cummings at the Spitalfields Festival as principal tenor soloist in the Monteverdi Vespers.
Simon has dipped his toe into the operatic pool, creating the role Owl as part of the vocal group I Fagiolini, in a brand new work, The Birds by Ed Hughes, which premiered at the City of London Festival in July 2005. More recently, Simon played Eco and covered Second Shepherd in Monteverdis Orfeo, conducted by Emmanuelle Haïm in Theatre Chatelet, Opera de Lille, and Opera du Rhin. He has recorded Barbers operetta A Hand of Bridge, conducted by Marin Alsop with the Royal Scottish National Orchestra (Naxos).
Simon is often invited to sing with top-notch consorts such as I Fagiolini, The Netherlands Bach Society, Polyphony, The Monteverdi Choir, The Cardinalls Musick, The Cambridge Singers, and The Gabrieli Consort.
Other recent and forthcoming work includes recordings of Caccini songs with La Nuova Musica, Charles Woods epic St Mark Passion (Evangelist) with the choir of Jesus College, Cambridge, Messiah at the Usher Hall in Edinburgh, Israel in Egypt with The Holst Singers and Academy of Ancient Music conducted by Stephen Layton, and a liturgical performance of Leightons Crucifixus pro nobis at Londons Temple Church.
Simon is taught by David Maxwell Anderson.