Gregory has been working in professional theatre for over 20 years as an actor, writer and director. He began his career at The Court Theatre in Christchurch and wrote some of their earliest school holiday productions. His children’s plays have had seasons at The Court, Downstage, and Fortune Theatre as well as touring schools throughout Australasia with New Zealand Playhouse & Australia Playhouse.
He co-wrote and performed in the highly acclaimed The Complete History of New Zealand (Abridged) and has also co-written The Complete History of Christchurch, NZ Rocks! (The Complete History of NZ Music) and The Complete History of World Rugby. His one man show MAMIL (Middle Aged Man In Lycra) starring Mark Hadlow toured in 2014 and 2015 with sell-out seasons throughout the country.
He co-wrote That Bloody Woman, a punk-rock musical about the life of Kate Sheppard, which premiered at the Christchurch Arts Festival in 2015. Auckland Theatre Company and The Court Theatre will co-produce seasons of That Bloody Woman in 2016. His latest play The Streaker will also have seasons at The Court and Centrepoint Theatre in 2016.