On one of his prison stretches he learned the game of chess from a cellmate, Harry the Brighton Fox. Finding that he had a special aptitude for the game, he decided to give up drinking, and with the help of his probation officer Clive Soley (now Clive Soley, Baron Soley) he made his first moves back into normal life. He has remained sober since.

His chess career continued for ten years and despite the ravages of his years on the street he became a highly rated player, capable of conducting four games at once, blindfolded.

Having given up his ambition of becoming a Grand Master, Healy retired from tournament chess and began to write his life story, which was published in 1988 by Faber and Faber. The Grass Arena was instantly recognised as a classic of the memoir genre, and won many awards including the J R Ackerley Award for Literary Autobiography. Reviews include the following:'Terrific' (Harold Pinter),'Brilliant' (The Guardian newspaper),'A Masterpiece' (Irvine Welsh),'The only book which even begins to evoke a real comparison in English is William Burroughs' Junkie ... Beside it, a book like Orwell's Down and Out in Paris and London seems like a rather inaccurate tourist guide' (Professor Colin McCabe),'Time and again one is appalled by the pleasure The Grass Arena furnishes as literature, when it is so very clearly not fiction. And this sense of the reader's dilemma as a privileged observer in a world of casual savagery that is palpably real is a troubling and thoroughly enriching one.' (Literary Review).

His second book, the novel Streets Above Us, fared less well and is currently out of print.

In 1990 the book was filmed, and the film, also titled The Grass Arena , won many awards, principally the inaugural Michael Powell Award for Best British Feature at the Edinburgh Film Festival .

A documentary about Healy's life and work, titled Barbaric Genius, directed by Paul Duane and produced by Screenworks Film and TV & Passion Pictures, is due to be premiered in 2010.

Following a dispute with Faber and Faber in 1991, the book went out of print in the UK, and remained so until 2008. It remained in print, however, in France, where it is published by Gallimard.

Republished in 2008 with a new introduction by actor Daniel Day-Lewis, the book has once again been accorded classic status by a new generation of readers.