His financial means being insufficient Head was taken from college and bound apprentice to a "Latin bookseller" in London "attaining to a good Proficiency in the Trade", as Winstanley put it.
Being a translation of part of Sinibaldus, his Geneanthropeia, and a collection of some things out of other Latin authors, never before in English (London: Philip Briggs, 1658).
Head moved – or fled – to his homeland Ireland, where he gained esteem with his first comedy Hic et ubique, or, The Humors of Dublin – printed with a dedication to James Scott, 1st Duke of Monmouth at his return to England in 1663.
Its tales of drastic adventures were based on the model of Spanish rogue stories (such as Lazarillo de Tormes 1554), which were fashionable due to the contemporary publication of Scarron's Roman Comique (or Comical Romance, so the English title which established the genre), and savoury with the events Head could claim to have based on his personal experience.
Its German title was Simplicianischer Jan Perus, dessen Geburt und Herkommen, kurtzweiliger Lebens-Lauff, unterschiedliche Verheyrathung, Rencke, Schwencke, Elend, Reise, Gefängnuß, Verurtheil- und Bekehrung (1672), – the title being designed to sell the English work on the very market Hans Jakob Christoffel von Grimmelshausen had recently created with his Simplicius Simplicissimus (1666–1668).
Numerous imitations of Head's rogue story followed on the English market such as The French Rogue: or, The Life of Monsieur Ragoue de Versailles (1672) (identified in several library catalogues as another of Head's works); the most famous descendant is today probably Daniel Defoe's The Fortunes and Misfortunes of the Famous Moll Flanders (1722).