Ives played the role of "the chain-smoking English teacher who coached the track team (while smoking)", and he wrote and performed a song.
This school experience, along with seeing a production of Edward Albee’s A Delicate Balance, starring Hume Cronyn and Jessica Tandy, were two early events that inspired his interest in theatre.
Ives wrote three full-length plays: St. Freud (1975), The Lives and Deaths of the Great Harry Houdini, and City of God.
In 1983 Ives was playwright-in-residence at the Williamstown Theatre Festival in Massachusetts where The Lives and Deaths of the Great Harry Houdini was produced.
[9][11][12] Ives' All in the Timing, an evening of six one-act plays, premiered at Primary Stages in 1993,[9] moved to the larger John Houseman Theatre, and ran for 606 performances.
[9][16][17] Ives’ full-length play Don Juan in Chicago premiered off-Broadway in New York at Primary Stages, on March 25, 1995.
cried Hamlet’s father's ghost in exasperation, and I couldn't agree more ..."[31][32] His translation of Georges Feydeau's farce A Flea in Her Ear was produced at Chicago Shakespeare in 2006, and won the Joseph Jefferson Award for "new adaptation".
[33] New Jerusalem, concerning the excommunication of Baruch Spinoza, opened Off-Broadway in January 2008 (previews from December 2007) in a Classic Stage Company production.
[37] Also in 2011 his adaptation of Jean-Francois Regnard’s Le Legataire universel premiered at the Shakespeare Theatre Company in Washington, D.C. under the title, The Heir Apparent.
[38][39] Venus in Fur opened Off-Broadway at the Classic Stage Company in January 2010 with Nina Arianda and Wes Bentley.
[45] The plays are: Enigma Variations, The Mystery at Twicknam Vicarage, Babel's in Arms, Soap Opera, Lives of the Saints, Arabian Nights, and Captive Audience.
[46] The Lives of the Saints was produced with five of the plays at the Berkshire Theatre Festival, Stockbridge, Massachusetts in August and September 1999.
[49] In April 2018, Red Bull Theater presented the New York premiere The Metromaniacs, his "translaptation"[50] of a rediscovered French farce by Alexis Piron at The Duke on 42nd Street directed by Michael Kahn.
series of American musicals in concert, starting with Out Of This World in 1995, Du Barry Was A Lady in 1996, and working on two or three a year until 2012.
adaptation of Wonderful Town moved to Broadway's Al Hirschfeld Theatre in 2003, directed by Kathleen Marshall.
He adapted David Copperfield's magic show, Dreams and Nightmares, which premiered on Broadway at the Martin Beck Theatre in December 1996.
[60] He co-wrote the book for Irving Berlin's White Christmas, which premiered in San Francisco in 2004[61] and then went on to tour across the United States.
[63] Ives began collaborating with Stephen Sondheim on a new untitled musical based on two films by Luis Buñuel, initially set to premiere in 2017.
[68] Renamed as Here We Are, the musical collaboration inspired by The Discreet Charm of the Bourgeoisie and The Exterminating Angel would have a limited engagement world premiere in September 2023, running through January 2024 at The Shed.