Gregory made his feature film debut in Jon Hewitt's Acolytes. He played Mark, a teenager who becomes involved in murder and violence. Principal photography on the film began in April 2007 in Queensland. Gregory's band, Menace, had two songs featured on the Soundtrack. Shortly after, Gregory was cast in Beautiful a film by writer-director Dean O'Flaherty. 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. But there's something really beautiful about Danny." Molitorisz said Gregory "delivers a powerfully understated performance in the film." For his portrayal of Danny, Gregory earned a nomination for Best Young Actor at the 2009 Australian Film Institute Awards.