- (1981 - 1982) Portrayed "Delahay" in Julian Mitchell's play, "Another Country", at the Greenwich Theatre, Croom's Hill, Royal Borough of Greenwich, and at the Queen's Theatre, Shaftesbury Avenue, City of Westminster, both theaters in London, England, UK.
- (2004) Also a director, he directed and starred in "Wheels Within Wheels," for TBFL productions, a documentary about cyclist Tommy Simpson, which took 4 years to complete.
- (1990) He Appeared in J.B. Priestley's play, "Time and the Conways," directed by Richard Olivier (his brother-in-law); with Joan Plowright, The Baroness Olivier, CBE (his mother-in-law); Julie Kate Olivier (his sister-in-law); and Tamsin Olivier (his wife) in the cast. Five family members in one stage production! The play was staged at The Old Vic (Theatre), London Borough of Lambeth, London, England, UK.
- (1987) He acted in Oscar Wilde's play, "The Importance of Being Earnest", at the Whitehall Theatre in London, England with Patrick Fyffe (played "Dame Hilda Brackett"), George Logan, (played "Doctor Evadne Hinge"), Robin Kermode, Kate O'Sullivan, Tara Ward, Chubby Oates and Fred Evans in the cast. Lou Stein was the director.
- (2003) Independent Short Film: "Mind Games". Starred Simon Dutton as "Bryce Reynolds", directed by Gerhard Paul Ackermann, written by Robert J Madison (as R.L. Kienbaum).
- (January-February 1986, June 1986, October-December 1986) He acted in the Royal National Theatre's Repertory Season at the Cottesloe Theatre, Lyttelton Theatre, and Olivier Theatre, all in the National Theatre complex, London, England, UK. The repertory season plays which Simon appeared in included Peter Shaffer's play, "Yonadab;" Tom Stoppard's plays, "The Real Inspector Hound," and "Dalliance;" Richard B. Sheridan's play, "The Critic;" Alan Ayckbourn's plays, "A Chorus of Disapproval," and "Tons of Money;" Howard Brenton's play, "Pravda;" Neil Simon's play, "Brighton Beach Memoirs;" William Congreve's play, "Love for Love;" George Bernard Shaw's play, "Mrs Warren's Profession;" John Webster's play, "The Duchess of Malfi,;" Stephen MacDonald's play, "Not About Heroes;" William Shakespeare's plays, "Hamlet," and "King Lear;" Athol Fugard's play, "The Road to Mecca;" Anton Chekhov's play, "The Cherry Orchard;" Bertolt Brecht and Kurt Weill's play, "The Threepenny Opera;" Sarah Daniels's play, "Neaptide;" Dusty Hughes's play, "Futurists" (its world premiere); David Wood's play, "The Pied Piper;" Richard Peaslee's play, "Animal Farm;" Franz Werfel's play, "Jacobowsky and The Colonel;" Arthur Wing Pinero's play, "The Magistrate;" David Hare's play, "The Bay At Nice;" Arthur Miller's play, "The American Clock;" Stephen Poliakoff's play, "Coming In To Land;" and Stanislaw Ignacy Witkiewicz's play, "The Mother;" with Robin Bailey, Desmond Barrit, Alan Bates, Suzanne Bertish, Brenda Blethyn, Eleanor Bron, Michael Bryant, Yvonne Bryceland, Selina Cadell, Simon Cadell, David Calder, Charlotte Cornwell, Gemma Craven, Tim Curry, Daniel Day Lewis, Frances De La Tour, Sally Dexter, Russell Dixon, Julian Fellowes, Alison Fiske, Michael Gambon, Robert Glenister, Sheila Hancock, Nigel Hawthorne, Anthony Head, Greg Hicks, Clare Higgins, Anthony Hopkins, Kelly Hunter, Geoffrey Hutchings, Jonathan Hyde, Barry Ingham, Sara Kestelman, Roy Kinnear, Leigh Lawson, Nicholas Le Prevost, Nigel Le Vaillant, Hugh Lloyd, Stephen Mackintosh, Anna Massey, Tim McInnery, Ian McKellen, Claire Moore, Stephen Moore, Wendy Morgan, Bill Nighy, Bob Peck, Edward Petherbridge, Joan Plowright, Amanda Redman, Moira Redmond, Jack Shepherd, Michael Simkins, Maggie Smith, Imelda Staunton, Patrick Stewart, Ken Stott, Zoe Wanamaker, Marcia Warren, Jane Wenham, and Irene Worth in the repertory cast.
- (June 7, 2006 - July 2, 2006) In addition to theatrical acting and directing, he is also a theatrical producer. One of his productions was "Nothing," written by Andrea Hart, from a novel of the same name by British author Henry Green, which was published in 1950. The production was co-produced with fellow actor Sophie Ward for the Brits Off Broadway festival, directed by Philip Prowse. The cast included producer Simon Dutton (portrayed John Pomfret), Candida Benson (portrayed Mary Pomfret), producer Sophie Ward (portrayed Jane Wetherby), Pete Ashmore (portrayed Philip Wetherby), playwright Andrea Hart (portrayed Liz Jennings), Derwent Watson (portrayed Richard Abbot), and Tristram Wymark (portrayed Gaspard).
- (1990) He acted in J.B. Priestley's play, "Time and the Conways," at the Old Vic Theatre in London, England with Joan Plowright, Tamsin Olivier, and Julie-Kate Olivier. Richard Olivier was director.
- (1993) He acted in for Jeffey Chiswick in Harold Pinter and Franz Kafka's play, "The Trial," in an European Stage Company production at the Young Vic Theatre in London, England with James Wilby, Peter Eyre, David Bamber, Malcolm Rennie, Guy Manning, Estelle Kohler, and Laura Cox in the cast. Lida Engelova was director.
- (1997) He acted in George Bernard Shaw's play, "Heartbreak House," at the Almeida Theatre in London, England with Richard Griffiths, Emma Fielding, Patricia Hodge, Penelope Wilton, Malcolm Sinclair, Peter McEnery, and John Bowe in the cast. David Hare was director.
- (2001) He acted in Valentine Guinness's play, "Helping Harry," at the Jermyn Street Theatre in London, England with Adrian Lukis, Jay Villiers, James Wilby, and David Michaels in the cast. Nickolas Grace was director.
- (2001) He acted in Noel Coward's play, "Semi-Monde," at the Lyric Theatre in London, England with Benedick Bates, Stefan Bednarczyk, John Carlisle, David Foxxe, Georgina Hale, Nichola McAuliffe, Ian Price, Frances Tomelty, Sophie Ward and Tristram Wymark in the cast. Philip Prowse was director.
- (2019) Played Ivor in Tom Stoppard's Rough Crossing at the Chichester Festival Theatre
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