[5] In the 1962–63 television season of Our Man Higgins, Holloway was cast in his first major acting role as Quentin in four episodes.

[7] In the 1970's British police drama The Sweeney,[7] episode Big Spender, Holloway appeared as John Smith, the brains of an organized crime family who involve themselves with two dishonest employees of a car park company in an elaborate fraud.

[7] His films include Young Winston (1972),[7] Porridge (1979),[7] The Great Rock 'n' Roll Swindle (1980),[7] A Christmas Carol (2009) and The Rum Diary (2011).

[6] In 1991, he performed the part of Captain Zed in Captain Zed and the Zee Zone and as Bradford Milbanks in James Bond Jr..[7] He also voiced Siegfried Fischbacher in Father of the Pride (2004), Prime Minister Almec in several episodes of Star Wars: The Clone Wars (2008–2020), and main antagonist Odlaw in Where's Waldo?

[7] Holloway also performed as a vocal artist for video games including Pirates of the Caribbean: At World's End and Medal of Honor: European Assault.