Halliwell attended Huddersfield College of Art as an art student, but was expelled for a time from the institution, and later switched to acting at RADA. It was there that Halliwell first met Mike Leigh. According to Leigh, the other students "were mostly posh kids and it was terribly old-fashioned and twee, not like it is now, but there was a scruff element. John Hurt was there, David Warner was there. Me, Halliwell, Ken Campbell and a few other renegades." In the early 1960s he worked as an actor in rep and was a stage manager at the Nottingham Playhouse for a time.
''Little Malcolm and His Struggle Against the Eunuchs''
His experiences at the Huddersfield College were the basis for his earliest produced and best remembered play, Little Malcolm and His Struggle Against the Eunuchs. In this play Malcolm Scrawdyke, a Hitlerite figure, plots revenge against authority for his college expulsion by forming the Party of Dynamic Erection with his three acolytes. "The Nazis made a big impression on people of my age", Halliwell recalled. "They almost destroyed Europe. But as well as being pretty threatening they were also seen as a laughing stock even during the war." The play won Halliwell the Evening Standard's Most Promising Playwright Award in 1967. Malcolm's premier production at the Unity Theatre in 1965 was directed by Mike Leigh with Halliwell himself in the central role of Malcolm. Lasting six hours in this version, the production's run was short. Taken up by West End producerMichael Codron, reduced to a more manageable length, John Hurt now featured as the character in a West End production and on Broadway where the play was retitled Hail Scrawdyke! A feature film version followed, Little Malcolm, again with Hurt in the lead. A successful revival in 1999 starred Ewan McGregor.
Later work
In 1968 Halliwell jointly set up a company named Quipu which performed at various London theatres until 1973. Its stated aim reflected the radical politics of the time: "a new kind of organisation in which the means of production are owned, controlled and developed by the artists whose work is being produced". Quipu, "the first lunchtime theatre club in London", allowed the tryout of short plays. It was a form of "devised theatre" which Mike Leigh, recalling Halliwell in 2015, thought his friend's personality was incompatible: "His relationship with the actors wasn’t about growing and enabling, but about dictating, so the plays were always somewhat inorganic. The writer was there, though. He had great ideas – perceptive to the highest degree and witty, too." Halliwell's later stage plays include Who's Who of Flapland and K.D. Dufford. Halliwell researched the professional relationship of Maurice Wilkins and Rosalind Franklin, both involved in the discovery of DNA, in the 1980s, but his work was not completed, although the recordings of people he interviewed have been preserved. He contributed several television scripts to several of the BBC's anthology series, including Play for Today, and wrote for Doctor Who.