[9] Head played Frank N. Furter in the 1990–91 West End revival of The Rocky Horror Show at London's Piccadilly Theatre, with Craig Ferguson as Brad Majors.

Head left the regular cast of Buffy during the show's sixth season and subsequently appeared several times as a guest star until the conclusion of the series.

[13] In 2002, he co-starred in the BBC Two television series Manchild, a show revolving around four friends approaching their fifties who try to recapture their fading youth and vitality while dealing with life as 'mature' men.

[15] He appeared in the fourth series of the British hit sitcom My Family in 2003, playing one of the main characters' (Abi's) father in the episode "May the Best Man Win".

[15] Head had previously auditioned for the role of the Eighth Doctor for the 1996 television film, but lost out to Paul McGann.

The same year he filmed a pilot for a new show entitled Him and Us, loosely based on the life of openly gay rock star Elton John, for American TV channel ABC, co-starring Kim Cattrall.

In 2007, he portrayed Stockard Channing's gay brother in the English film Sparkle,[12] and appeared as Mr. Colubrine in the ITV1 comedy drama Sold.

[15] 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!

He also had a significant recurring role in the last two series (2011–13) of the Radio 4 sitcom Cabin Pressure as Hercules Shipwright, a romantic interest for the airline CEO played by Stephanie Cole, and returned for show's two-part finale in 2014.

Head also provided voice-over work for the Nintendo Wii video game Flip's Twisted World, developed by Frozen North Productions.

[12] From 2020 to 2023, he played former Richmond F.C owner Rupert Mannion, in Ted Lasso alongside Jason Sudeikis and Hannah Waddingham.

[15] For his role in the final season, Head was nominated alongside the rest of the cast for the Screen Actors Guild Award for Outstanding Performance by an Ensemble in a Comedy Series.

[22] Head reprised his role as Giles in the Audible exclusive audio series Slayers: A Buffyverse Story alongside his former Buffy co-stars James Marsters, Charisma Carpenter, Amber Benson, Juliet Landau, Emma Caulfield Ford, James Charles Leary and Danny Strong.