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| Born in London, Simon Keenlyside as a child attended St. John's College School, Cambridge, and toured and recorded with the school's choir. He studied zoology at Cambridge University, and, after graduation from Cambridge, resumed vocal studies at the Royal Northern College of Music in Manchester. He has had a successful career as a baritone in opera and song. |
| Simon Keenlyside and accompanist Malcolm Martineau gave a recital at the Herbst Theatre in San Francisco on April 30, 2002. The review in the San Francisco Chronicle of May 2, 2002, spoke of jet lag and "bleary, unshaven demeanor." |
| In a review of the Met's Il Barbiere di Siviglia published in the New York Times of April 16, 2002, Anne Midgette says that Simon Keenlyside was replaced as Figaro because of a motorcycle accident.. |
| "[T]his is some of the most perfect singing I've heard," wrote Anna Picard in a review dated 31 March 2002 for The Independent about a (recital) performance of Winterreise by Simon Keenlyside at Wigmore Hall. |
| Simon Keenlyside sang Rodrigo in concert performances of Verdi's Don Carlo (in Italian) with the Cleveland Orchestra in Cleveland, Ohio, on June 5 and 7, 2003. |
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| Simon Keenlyside is well known for his appearances as Papageno in Die Zauberflöte. The DVD of the Covent Garden production of Mozart's Die Zauberflöte with Dorothea Röschmann and Simon Keenlyside was released at amazon.co.uk and at amazon.de on 1 September 2003. Mozart: Die Zauberfloete, DVD, amazon.com 
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| The Tempest, a co-production with the Royal Danish Opera and the Opera du Rhin in Strasbourg, France, opened February 10, 2004, at the Royal Opera, Covent Garden. Simon Keenlyside was Prospero, Ian Bostridge was Caliban, Cynthia Sieden was Ariel in her Royal Opera debut and the opera's composer Thomas Ades conducted in his company debut. The libretto is by Meredith Oakes, and the production is by Tom Cairns.--from an Associated Press report of March 27, 2003. |
| Simon Keenlyside sang the title role in performances of Ambroise Thomas's opera Hamlet at the Royal Opera, Covent Garden, on 12, 15, 20, 23, 28, 30 May 2003 at 7pm. |
| Richard Strauss's Capriccio on DVD (with encoding for United States and Canada) with Kiri Te Kanawa, David Kuebler, and Simon Keenlyside can be ordered from amazon.com. And from amazon.co.uk (release date 1 September 2003). |
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| "Two of Britain's most distinguished concert singers, tenor Anthony Rolfe Johnson and baritone Simon Keenlyside, do the vocal honours, superbly accompanied by pianist Graham Johnson," wrote William Littler at thestar.com (Toronto Star) about this recording. |
| A Classics for Pleasure compact disc Schubert: Favourite Lieder with Simon Keenlyside was released on 1 September 2003 and can be ordered from amazon.co.uk. |
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| Le Nozze di Figaro was released at amazon.fr on 12 March 2004. amazon.co.uk. amazon.com. Le Nozze di Figaro, amazon.de |
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| "Some singers might be daunted by the part of Prospero in Thomas Adès' challenging 'The Tempest', but not baritone Simon Keenlyside. Jessica Duchen meets the king of barnstorming performances" Published: 12 March 2007, independent.co.uk |