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Head left the regular cast of Buffy during the show's sixth season and subsequently appeared several times as a guest star through the conclusion of the series.
In July he appeared as Captain Hook at the Children's Party at the Palace, a live pantomime staged in the grounds of Buckingham Palace as part of Queen Elizabeth II's 80th birthday celebrations.
In 1991 Head's rendition of "Sweet Transvestite" was released as a single by Chrysalis Records.
Head played the role again in the summer of 1995 at London's Duke of York's Theatre, a tribute show at London's Royal Court Theatre, and a 14 October 2000 production at the Hard Rock Hotel and Casino, Las Vegas, Nevada.
Success on the stage and a number of brief appearances on American television, such as in the short-lived VR.5, led to accepting the role of Rupert Giles in Buffy the Vampire Slayer in 1997.
For this role he lived full-time in the United States during the late 1990s and early 2000s, although his family continued to live in the UK.
After seeing Anthony Head in the Buffy musical episode, "Once More With Feeling", Saw director Darren Lynn Bousman cast him in his 21st century rock opera, Repo! shortly before the film's release on 7 November 2008.