In 1994, Dickens turned to playwriting from acting when he developed advanced glaucoma.[4] He was commissioned by Die In Debt Theatre to write a new version of Seneca's Oedipus .[2] After writing the piece and winning a Dora Award, Dickens wanted to further explore the story of Jocasta, Oedipus's mother. He then became fascinated by "the aftermath of Oedipus's downfall."[4] After six years, Dickens had expanded Oedipus to become a trilogy and decided to "dramatize the entire history of Thebes."[4] In total, the series took 15 years to write.[5] To support himself during this time, Dickens taught public speaking to politicians and worked in construction, injuring his hand in an accident.[5]
In May 2009, Dickens's seven-play cycle, City of Wine, debuted at Toronto's Theatre Passe Muraille.[6][7] The play involved 233 student actors, 172 professional actors, and 110 theatre artists[6] and was produced by Nightswimming, an independent theatre company.[5] In its entirety, the play's running time is 12 hours. Robert Kushman, in the National Post, described it as a "dizzyingly ambitious feat of producing and a dizzying achievement."[6]