Freeman's first role was playing Chris Longworth in children's school soap Grange Hill. After leaving Grange Hill, when Emmerdale decided to recast the character of Scott Windsor from incumbent Toby Cockerell in 1998, Freeman won the role of the womanising car mechanic Scott. Following Emmerdale, Freeman took to the stage, playing the part of The Prince in Romeo and Juliet, Warner in the final cast of Legally Blonde and Norman in Dreamboats and Petticoats, both in London's West End. On 29 October 2012 he opened in Wicked in the West End playing the role of the love interest Fiyero. He left the show on 16 November 2013 and immediately joined the UK touring cast of a new musical version of Happy Days playing the role of The Fonz. The tour finished in July 2014.