He has starred in several films including Fallen Dreams, Suzie Gold, Green Street, Stoned, Tristan + Isolde, Perfect Creature, The Mark of Cain, Daylight Robbery, Act of Grace, Cass, Revert, The Big I Am, Throne: Scaredycat, Big Fat Gypsy Gangster, Wild Bill, Payback Season, One in the Chamber, All Things to All Men, Top Dog, The Hooligan Factory, The Ninth Cloud, Northmen – A Viking Saga, and more. Gregory has also appeared in episodes of the TV series Jewels, EastEnders, Menace, Above Suspicion, Silent Witness, Mrs. Biggs, Law & Order: UK, The Team, and more. In 2006 he was nominated for an Empire Award for Best Newcomer for Stoned.