Simon Keenlyside was born in London. He made his operatic debut at the Hamburg State Opera as Count Almaviva (Le Nozze di Figaro). He has since sung in Geneva (Hamlet, Pelleas and Oreste), Zurich (Don Giovanni and Szenen in Goethe's Faust), Barcelona (Don Giovanni and Hamlet), Madrid (Posa), San Francisco (Pelleas and Olivier), Brussels (Don Giovanni and Orfeo), Paris (Papageno, Pelleas, Dandini, Guglielmo, Yeletsky and Wozzeck), Vienna (Macbeth, Eugene Onegin, Marcello, Figaro, Count Almaviva, Billy Budd, Don Giovanni, Papageno and Posa), Munich (Don Giovanni, Marcello, Count Almaviva and Wolfram), Tokyo (Don Giovanni with La Monnaie, Wolfram with the Bayerische Staatsoper, Count Almaviva with the Vienna State Opera and Germont Pere with the Royal Opera House, Covent Garden), at the Metropolitan Opera, New York (Hamlet, Posa, Belcore, Marcello, Papageno and Count Almvaviva), the Salzburg Festival (Count Almaviva, Guglielmo and Papageno) and Salzburg Easter Festival (Pelleas), La Scala, Milan (Papageno, Count Almaviva, Belcore and Ubalde), in Ferrara (Don Giovanni), and at the Royal Opera House, Covent Garden (Billy Budd, Valentin, Pelleas, Posa, Belcore, Marcello, Count Almaviva, Don Giovanni, Guglielmo, Papageno, Hamlet and Prospero). For Billy Budd at ENO and Winston (1984) at the Royal Opera House, he won the 2006 Olivier Award for outstanding achievement in Opera. In 2007 he was given the ECHO Klassik award for male Singer of the Year, and in 2011, he was honoured with Musical America’s Vocalist of the Year Award.

He will return to the Vienna State Opera (Posa, Renato, Rigoletto and Wozzeck), the Royal Opera House (Germont Père, Macbeth and Count Almaviva) and the Bayerische Staatsoper (Eugene Onegin, Count Almaviva and Wozzeck).

Simon enjoys extensive concert work and has sung under the baton of many of the worlds’ leading conductors, appearing with the Chamber Orchestra of Europe, the Berlin Philharmonic, the City of Birmingham and London Symphony Orchestra, the Philharmonia Orchestra, the Cleveland Orchestra, and the Vienna Philharmonic to mention a few.

A renowned recitalist Simon appears regularly in most of the world’s major recital venues. He has recorded four recital discs with Malcolm Martineau, of Schubert, Strauss, Brahms, and most recently, an English song disc to be released this autumn, as well as a disc of Schumann's Lieder with Graham Johnson.

He has also recorded Des Knaben Wunderhorn under Rattle, the title role in Don Giovanni under Abbado, Carmina Burana under Thielemann, Marcello in La Bohème under Chailly, the title role in Billy Budd under Hickox, Papageno in The Magic Flute under Mackerras and Count Almaviva in the Grammy award-winning Le Nozze di Figaro under Jacobs. For Sony BMG Simon has released an orchestral arias disc, which won the Gramophone 2007 best recital award and an operetta disc with Angelika Kirchschlager.

Simon was made a CBE in 2003.