As the founder and director of the Emerald Hill Theatre Company in Melbourne, Victoria, Cherry gained a reputation in the early 1960s for innovative programming and bold productions, particularly of Australian plays.
[2] He was also a champion of Bertolt Brecht, both for his plays and his contributions to theatre theory (especially the so-called "alienation effect" or Verfremdungseffekt).
In its first year, the fledgling Drama Department at Flinders had a staff of only two (Cherry and ex-ABC Radio man George Anderson), but Cherry's energy and high-profile drove significant expansion, and by the mid-1970s, the department had over a dozen staff, teaching drama as both an academic discipline, and as training for professional careers in theatre and film, a unique approach at the time.
In that position, he drove significant changes in the direction of the company, but his objective of a continuing close link between the SATC and the Flinders Drama Department was never realised.
On-campus, in 1971-2 he wrote and directed a play, Horrie's Alibi, with a student cast augmented by a number of professional actors.