Educated at the London Academy of Music and Dramatic Arts, Head began his career on stage; his extensive theater work has included Joseph and the Amazing Technicolor Dreamcoat, Godspell, Chess, The Pirates of Penzance, and appearing as Dr. Frank N Furter in the London revival of The Rocky Horror Show. His television career began in 1979 with an appearance in the ITV series Enemy at the Door. Following the success of the Taster's Choice adverts, Head began to look for more work in the United States. In 1995, Head appeared in the shortlived American drama series VR-5. It was this role, plus his stage work, that led to his winning the part of Rupert Giles in 1997.