[4] Two years later, he played the recurring role of Garrett Burns, a love interest for Rachel Kinski (Caitlin Stasey), in the soap opera Neighbours.
[2][8] Of his role as Danny in the film, Gregory told Sacha Molitorisz of The Sydney Morning Herald "I always seem to be playing a weird, freaky kid.
"[2] For his portrayal of Danny, Gregory earned a nomination for Best Young Actor at the 2009 Australian Film Institute Awards.
[9] Gregory was cast in the regular role of JB Deekes in the children's television series The Elephant Princess in 2008.
[3] In June 2008, Gregory joined the cast of the dark comedy film Accidents Happen,[8] which is based on a semi-autobiographical screenplay by Brian Carbee.
[8][13] In April 2012, it was announced Gregory had re-joined the supporting cast of Neighbours as "mathematics genius" Ed Lee.
[16] He also stars as a struggling artist amidst the American heroin epidemic in the 2018 drama film Shooting in Vain.