Gregory got his start acting in the teen ghost comedy The Heavenly Kid (1985) with Voyager guest Mark Metcalf, which remains to this day as Gregory's sole film work. Gregory then found himself only working in guest roles. The first was on the medical drama St. Elsewhere starring Ed Begley, Jr., Bruce Greenwood, and Norman Lloyd in "Getting Ahead" (1987), followed by the teen crime drama 21 Jump Street in the interestingly titled "Next Generation" with fellow TNG guest Michael Ensign. Gregory's last single guest appearance was on the short-lived Houston Knghts in "Bad Paper" with Nicholas Worth.