Baptised at Irstead, Norfolk, 27 April 1765, he was only son of Henry Headley, rector of that parish to 1768, and then vicar of North Walsham to his death on 6 October 1785, at the age of 57; his mother, Mary Anne Barchard, married (on 21 September 1789), after her first husband's death, Anthony Taylor of Gorleston, Great Yarmouth, and died 13 October 1818, at age 85.
With a letter of recommendation from William Windham he was admitted into the house of Lewis de Visme at Cintra, but his strength declined.
An elegant inscription, composed, at the widow's request, by William Benwell, for a monument to his memory, was made public by Henry Kett in 1790.
[1] The Critical Remarks of the late Henry Headley, which were added to an edition of Phineas Fletcher's Purple Island in 1816, were extracts from the Select Beauties.
A writer in Blackwood's Magazine in 1835 drew attention to wholesale plagiarism from Headley's notes and criticisms in Robert Anderson's Collection of the Poets.
It was included in Bowles's Sonnets and other Poems, was prefixed, with the lines by Henry Kett, to a reissue of Select Beauties.
[1] Headley published anonymously in 1785 a volume of Fugitive Pieces, all of which were written at the age of 19, and most of which had previously appeared in print.
[1] To the Olla Podrida of Thomas Monro, a close friend at school and college, Headley contributed a number on the horrors depicted by the authors of modern tragedies' and he is said to have been one of the writers in The Lounger's Miscellany, or the Lucubrations of Abel Slug, Esq., which ran to twenty numbers in 1788 and 1789.
[1] During his vacation visits from Oxford to his friends in Norfolk, Headley fell in love, with a woman referred to in his poems as Myra.