Gregory’s career began at The Court Theatre in 1993. His previous Court Theatre credits include The Complete History of New Zealand, The Underpants, The Hound of the Baskervilles, Niu Sila, Uncle Vanya, Easy Money, A Christmas Carol, Elling, Les Liaisons Dangereuses, and The Wind in the Willows.
His other theatre credits include The Complete History of Christchurch, The Complete History of World Rugby, Howzat! The Complete History of Kiwi Cricket (CCC Summer Theatre season), Le Sud (Auckland Theatre Company), Niu Sila (Fortune Theatre), and The Complete History of the Royal New Zealand Navy (RNZN).
He wrote MAMIL (Middle Aged Man in Lycra), MAMIL 2: GOMIL (Grumpy Old Man In Lycra), The Streaker, Mr & Mrs Macbeth, and co-wrote the suffragist rock musical That Bloody Woman. His directing credits include MAMIL, GOMIL, Mr & Mrs Macbeth, Steel Magnolias (Court Theatre), 2Graves (LAF), and the pantomimes Cinderella and Beauty & The Beast (GMG Productions).
Court Shows
- 2025 - The End of the Golden Weather - Firpo
- 2024 - Mr and Mrs Macbeth of Heathcote Valley Road - Director
- 2022 - Flagons and Foxtrots - Understudy – Sid Jenkins
- 2020 - Lysander's Aunty - Theseus
- 2019 - The Wind in the Willows - Ratty
- 2019 - O Le Malaga Fa’a’Atua (The Journey of the Gods) - Director
- 2019 - Les Liaisons Dangereuses - Azolan
- 2019 - Elling - Frank Asli, Poet
- 2018 - A Christmas Carol - Actor
- 2018 - Roger Hall's Easy Money - Nigel de Lacy
- 2017 - Steel Magnolias - Director
- 2017 - Hamlet: The Video Game (the stage show) - Director
- 2017 - Uncle Vanya - Telegin
- 2016 - That Bloody Woman - Co-writer
- 2016 - The Streaker - Playwright
- 2015 - MAMIL - Writer / Director
- 2015 - Niu Sila - Peter Burton
- 2014 - Rumpelstiltskin - Playwright
- 2014 - The Hound of the Baskervilles - Sherlock Holmes + others
- 2014 - The Emperor's New Clothes - Playwright
- 2013 - A Very Merry Scriptless - Director
- 2013 - Beauty and the Beast - Playwright
- 2010 - Two Fish ’n' a Scoop - Director
- 2009 - Rumpelstiltskin - Playwright/Director
- 2009 - Poe - Edgar Allan Poe
- 2008 - Pulp William - Director
- 2004 - The Underpants - Benjamin Cohen
- 2001 - Dr. Pussyfinger Says No To Tomorrow - Writer, Actor
- 2000 - I Scream - Charles
- 2000 - Sick - Actor
- 1998 - The Complete History of New Zealand (abridged) - Actor