He went into business early in Mary's reign in partnership with John Tisdale, in Holborn.
His address was the Half-Eagle and Key in the Barbican, and in one of the Marprelate tracts it is stated that as printer to the Earl of Arundel he had a press in the Charterhouse.
He was known to be one of the ring-leaders of the gang of printers who printed copies of texts to which they had no rights.
Charlewood obviously hoped that this stratagem would provide easier and increased sales for these books, which would allow the printing of a larger and more profitable edition.
His hopes were apparently not realised since none of them were reprinted in Italian in Great Britain until modern times.