06/08/2026
John Herbert was convicted of indecency after he was robbed in Toronto while dressed as a woman.
His time in prison inspired him to write a play about his experience. It became the most-widely produced play in the history of Canadian theatre.
This is his story.
John Herbert was born on Oct. 13, 1926 in Toronto.
In the 1940s, he began to compete in drag pageants.
One day while out in Toronto, he was the victim of an attempted robbery. Instead of being seen as the victim, he was considered a perpetrator.
As he was dressed as a woman, his assailants falsely claimed he had solicited them for s*x. Herbert was convicted of indecency and sent to a youth reformatory in Guelph.
After his release, he worked odd jobs around North America to make money.
He returned to Toronto in 1955 and studied at the National Ballet School of Canada.
Wanting to document his time behind bars, he wrote Fortune and Men's Eyes in 1964. The character of Queenie represented himself during his time in prison.
In 1965, the play was staged at the Young Actor's Workshop at the Stratford Festival and was directed by Bruno Gerussi but festival directors refused to stage it publicly.
Due to the subject matter, no theatre company would mount a full production in Canada.
Herbert sent it to theatre critic Nathan Cohen, who then gave it to David Rothenberg. He recommended it to Dustin Hoffman who workshopped the play at the New York Actors Studio in 1966.
It premiered off-Broadway at the Broadway Actor's Playhouse on Feb. 14, 1967.
The play explored the themes of homos*xuality through Smitty, a 17-year-old sent to a youth reformatory. The title refers to the opening line of Shakespeare's Sonnet 29.
In 1969, the play was directed by Sal Mineo at the Coronet Theatre in Los Angeles. Don Johnson played the lead role.
A film adaptation was released in 1971, it won two Canadian Film Awards.
It also led to the formation of the Fortune Society.
Herbert continued to write plays and worked as a dancer, acting teacher and theatre director.
He died on June 22, 2001 in Toronto.
The typewriter he used to write Fortune and Men's Eyes was placed in the Canadian Le***an and Gay Archives.
I hope you enjoyed that look at John Herbert.
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