[18] In 1617, Draper became a barrister at Gray's Inn and released Ogilby, who by then was highly accomplished as a dancer and a teacher, from the apprenticeship, allowing him to set up as a master in his own right and to take part in theatrical performances.

According to Ashmole's horoscope, in 1625, Ogilby suffered from a "double quotidian ague" – a form of malaria – [20] he most probably contracted while fighting in the Low Countries under Colonel Sir Charles Rich.

[22] From June to November 1627, Ogilby was one of the few survivors of the ill-fated English Siege of Saint-Martin-de-Ré, returning to England as acting Captain of a supply ship.

[26] In 1637, as a consequence of this enterprise and to discourage competitors, Wentworth appointed Ogilby Master of the Revels for Ireland, with power to permit and forbid performances.

[30][31] The manuscript of his Virgil translation, which he had carefully placed in waterproof wrapping,[32] survived the incident and was published in October 1648 with the sponsorship of Royalist gentlefolk and nobility.

[38] During the next few years, Ogilby learnt Greek with the intention of creating and publishing a new translation of Homer's Iliad; he planned it to be a magnificent undertaking with an estimated production cost of £5,000.

[37] During the Great Fire of London in 1666, Ogilby's house in Shoe Lane, together with its printing works and most of his stock, was destroyed; he estimated he had lost £3,000.

[49][i] After the Great Fire, the Corporation of London appointed Ogilby and his wife's grandson William Morgan as "sworn viewers", members of a group of four trustworthy gentlemen directed by Robert Hooke,[50] to plot disputed property in the city.

[61] The cost of the survey and the resulting maps is not known but in a prospectus, Ogilby quotes a preiminary estimate made by the "Lords Referees" – advisors to the Privy Council – as £14,000 (equivalent to about £2.9 million today).

[68] The value of his estate is not recorded but the British Museum has a copy of an announcement by Robert Morden, a factor, of a sale of "undisposed" books and maps from Ogilby's collection with an asserted value of £517.50 (equivalent to about £115,000 today).

[69] In the years that followed his death, Ogilby's reputation as a poetic translator suffered from attacks made on him by John Dryden in his satirical work MacFlecknoe, and by Alexander Pope in The Dunciad.

Following their lead, Scottish philosopher David Hume used Ogilby's work to illustrate the idea that common sense frequently appeals to a "standard of taste" in aesthetic matters: Whoever would assert an equality of genius and elegance between Ogilby and [John] Milton, or [John] Bunyan and [Joseph] Addison, would be thought to defend no less an extravagance, than if he had maintained a mole-hill to be as high as Teneriffe [sic], or a pond as extensive as the ocean.

[70]Other writers were even more critical; Ogilby's entry in the Encyclopaedia Londinensis (about 1800) reads: The chief merit of his Homer consists in a commendable and uniform fidelity to the sense of his author.

As a poet, his pretensions to praise of any kind can scarcely be supported: he has neither animation of thought, accuracy of taste, sensibility of feeling, nor ornament of diction.