| Year | Title | Role | Notes |
| 1995 | The Tempest | Prospero | For the New York Shakespeare Festival, with the production later transferring to Broadway |
| 1997 | Othello | Othello | The Shakespeare Theatre Company's (Washington, D.C.) "photo negative" production of a white Othello with an otherwise all-black cast |
| 2000 | The Ride Down Mt. Morgan | Lyman Felt | On 9 April 2000, Stewart opened in Arthur Miller's The Ride Down Mt. Morgan at the Broadway Ambassador Theatre. |
| 2001 | Who's Afraid of Virginia Woolf? | George | Edward Albee's play at the Guthrie in Minneapolis |
| 2001 | Johnson Over Jordan | Robert Johnson | J.B. Priestley's play at the West Yorkshire Playhouse in Leeds |
| 2003 | The Master Builder | Halvard Solness | Henrik Ibsen's play at the Albery Theatre, London |
| 2003 | The Caretaker | Davies | Harold Pinter's play in Broadway's American Airlines Theatre |
| 2006 | The Tempest | Prospero | At the Royal Shakespeare Theatre and then the Novello Theatre |
| 2006 | Antony and Cleopatra | Mark Antony | At the Swan Theatre, for the Royal Shakespeare Company as part of the cycle performing all Shakespeare's works in a year |
| 2007 | A Christmas Carol | All | By Charles Dickens. Played 40 roles in a one-man performance at the Albery Theatre in the West End of London. |
| 2007 | Twelfth Night | Malvolio | At Chichester Festival Theatre's 2007 summer festival with a Scottish accent and kilt in Philip Franks' main house staging |
| 2007 | Macbeth | Macbeth | In Rupert Goold's revival in the Minerva studio theatre. The Chichester production of Macbeth transferred to the Gielgud Theatre in London's Shaftesbury Avenue. |
| 2008 | Macbeth | Macbeth | At the Brooklyn Academy of Music in New York City |
| 2008 | Macbeth | Macbeth | At the Lyceum Theatre, New York |
| 2008 | Hamlet | Claudius and the Ghost | Alongside David Tennant as the eponymous Hamlet with the Royal Shakespeare Company in Stratford-upon-Avon. This was later made into a television play and broadcast on BBC1 on 26 December 2009. |
| 2009 | Waiting for Godot | Vladimir (Didi) | Alongside Ian McKellen as Estragon (Gogo) |
| 2010 | Bingo: Scenes of Money and Death | William Shakespeare | By Edward Bond at the Chichester Festival Theatre, transferring to the Young Vic Theatre in February 2012. This was a role he had first performed in 1976 at The Other Place, Stratford. |
| 2011 | The Merchant of Venice | Shylock | In Rupert Goold's production |