Gregory has been a professional actor, writer and director for over 25 years. He began his career at The Court Theatre in Christchurch and wrote and directed some of their earliest school holiday productions. Since then his children’s shows have been produced and toured by numerous companies including The Fortune Theatre, New Zealand Playhouse and Australia Playhouse.

Gregory also co-wrote and directed the New Zealand tours of The Complete History of New Zealand and The Complete History of World Rugby for the Real New Zealand Festival as part of the Rugby World Cup celebrations in 2011. He also co-wrote and directed The Complete History of Christchurch that played to over 25,000 people in Hagley Park as part of the Christchurch City Council Summer Theatre season in 2012

In 2014 he wrote and directed Mark Hadlow’s one man show MAMIL (Middle Aged Man In Lycra). Since then the show that has been performed over 250 times nationwide with interest from Australian and UK producers to take offshore. He was also commissioned by the Royal New Zealand Navy to write The Complete History of the Royal New Zealand Navy for their 75th Anniversary Celebrations in 2016.

In 2015 he co-wrote That Bloody Woman, a musical about Kate Sheppard that played to capacity audiences at the Christchurch Arts Festival, Auckland Theatre Company and The Court Theatre before touring nationwide.

In 2016 his latest show The Streaker was staged by The Court Theatre and Centrepoint Theatre in Palmerston North.

Most recently Gregory has directed Steel Magnolias and O Le Malaga Fa’a’atua (The Journey of The Gods) for The Court Theatre and has also been commissioned to write a new main stage show entitled The United States of Aotearoa.