Herbert was born in Toronto on October 13, 1926. After completing high school, he worked in the advertising department of
Eaton's and began competing in
drag pageants. After being convicted, Herbert served time in a youth
reformatory in
Guelph, Ontario. Herbert wrote ''
Fortune and Men's Eyes'' in 1964 based on his time behind bars. He included the character of Queenie as an authorial
self-insertion. The play was first staged as a
Stratford Festival workshop directed by
Bruno Gerussi, in 1965, but Herbert was unable to find a theatre company willing to mount a full production in Canada. Because of his past conviction, Herbert faced difficulties entering the United States to attend productions of his work. The play had a profound impact on producer David Rothenberg. Rothenberg went on to found the
Fortune Society, a nonprofit advocacy organization that supports incarcerated and formerly-incarcerated people reintegrate into society. A selection of manuscripts, letters and personal papers were donated to the University of Waterloo Library in 1982. ==Selected works==