The most important primary source on Head’s life is William Winstanley's biographical entry published in his Lives of the most famous English poets (1687) — a credible if not reliable source insofar as Winstanley could claim to have been personally acquainted with Head. According to Winstanley, Head was a minister’s son, born in Ireland. His father was killed in the Irish rebellion of 1641, the incidents seem to be reflected in Head's English Rogue, the satirical romance he published in 1665. His mother took him to England where she had relatives in Barnstaple. They later moved on to Plymouth, to Bridport and to Dorset where Head is known to have attended the town's grammar school in 1650. Head was eventually admitted to the same Oxford College his father had attended (possibly New Inn Hall, from which a John Head graduated in 1628). 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.

“His genius being addicted to Poetry” he published his first poetical and satirical piece which Winstanley recorded as Venus Cabinet Unlock’d. This may be a reference to Giovanni Benedetto Sinibaldi's The cabinet of Venus unlocked, and her secrets laid open. 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 married around that time. A second addiction to gambling cost him the profit he made as an author and with his shop.

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 the Duke of Monmouth at his return to England in 1663. The Duke’s recompense remaining below expectations Head had to survive as a bookseller with shop addresses (so Sidney Lee) in Little Britain, and (so Gerard Langbaine) in Petty Canons Alley, off Paternoster Row and opposite Queen's Head Alley. Winstanley located him in Queen's Head Alley. If his reports are trustworthy, Head gathered some wealth in little time only to gamble it away again a little later.

The English Rogue (1665) solved some of his financial problems. 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 savory with the events Head could claim to have based on his personal experience. The censor, so Winstanley reported, rejected the manuscript as “too much smutty”. The softened book edition sold brilliantly and created a complex publishing history: The first edition published by Henry Marsh sold out within the year. Marsh died that very year, Francis Kirkman the business partner, to whom Marsh had been indebted, secured the rights and sold Head's title in four further editions between 1666 and 1667. It remains unclear how the ensuing volumes two, three, and four, published in 1671, 1674 and 1680, came to be written (a fifth was promised and never appeared). Winstanley speaks of Head as the author indiscriminately. In the dedication to his Proteus redivivus (1675) Head, however, explicitly denies a hand in any part but the first. Kirkman asserted nonetheless that he and Head were responsible for the third and fourth parts. The preface to the latter is signed by both men — facts which make Head's belated disclaimer suspicious.

Head's imprint as a publisher is found on several titles. Works from his pen appeared until 1677. Winstanley reports that Head drowned on a journey to the Isle of Wight; the report itself was made in June 1686, and this generally accepted as the date of his death, even though more accurately it is a terminus ante quem.

Richard Head's English Rogue became the first work of English prose fiction to be translated into a continental language. 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 Defoes The Fortunes and Misfortunes of the Famous Moll Flanders (1722).