- The Lady of May – This is one of Sidney's lesser-known works, a masque written and performed for Queen Elizabeth in 1578 or 1579.
- Astrophel and Stella – The first of the famous English sonnet sequences, Astrophel and Stella was probably composed in the early 1580s. The sonnets were well-circulated in manuscript before the first (apparently pirated) edition was printed in 1591; only in 1598 did an authorised edition reach the press. The sequence was a watershed in English Renaissance poetry. In it, Sidney partially nativised the key features of his Italian model, Petrarch: variation of emotion from poem to poem, with the attendant sense of an ongoing, but partly obscure, narrative; the philosophical trappings; the musings on the act of poetic creation itself. His experiments with rhyme scheme were no less notable; they served to free the English sonnet from the strict rhyming requirements of the Italian form.
- The Countess of Pembroke's Arcadia – The Arcadia, by far Sidney's most ambitious work, was as significant in its own way as his sonnets. The work is a romance that combines pastoral elements with a mood derived from the Hellenistic model of Heliodorus. In the work, that is, a highly idealised version of the shepherd's life adjoins (not always naturally) with stories of jousts, political treachery, kidnappings, battles, and rapes. As published in the sixteenth century, the narrative follows the Greek model: stories are nested within each other, and different storylines are intertwined. The work enjoyed great popularity for more than a century after its publication. William Shakespeare borrowed from it for the Gloucester subplot of King Lear; parts of it were also dramatised by John Day and James Shirley. According to a widely-told story, King Charles I quoted lines from the book as he mounted the scaffold to be executed; Samuel Richardson named the heroine of his first novel after Sidney's Pamela. Arcadia exists in two significantly different versions. Sidney wrote an early version (the Old Arcadia) during a stay at Mary Herbert's house; this version is narrated in a straightforward, sequential manner. Later, Sidney began to revise the work on a more ambitious plan, with much more backstory about the princes, and a much more complicated story line, with many more characters. He completed most of the first three books, but the project was unfinished at the time of his death—the third book breaks off in the middle of a swordfight. There were several early editions of the book. Fulke Greville published the revised version alone, in 1590. The Countess of Pembroke, Sidney's sister, published a version in 1593, which pasted the last two books of the first version onto the first three books of the revision. In the 1621 version, Sir William Alexander provided a bridge to bring the two stories back into agreement.<Evans, 12-13> It was known in this cobbled-together fashion until the discovery, in the early twentieth century, of the earlier version.
- An Apology for Poetry (also known as A Defence of Poesie and The Defence of Poetry) – Sidney wrote the Defence before 1583. It is generally believed that he was at least partly motivated by Stephen Gosson, a former playwright who dedicated his attack on the English stage, The School of Abuse, to Sidney in 1579, but Sidney primarily addresses more general objections to poetry, such as those of Plato. In his essay, Sidney integrates a number of classical and Italian precepts on fiction. The essence of his defence is that poetry, by combining the liveliness of history with the ethical focus of philosophy, is more effective than either history or philosophy in rousing its readers to virtue. The work also offers important comments on Edmund Spenser and the Elizabethan stage.
- The Sidney Psalms – These English translations of the Psalms were completed in 1599 by Philip Sidney's sister Mary.
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