Philip Sidney

The Gentleman-Poet of Elizabethan England

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Harrison W. Mark
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published on 29 May 2025
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Sir Philip Sidney (by Unknown Artist, Public Domain)
Sir Philip Sidney
Unknown Artist (Public Domain)

Sir Philip Sidney (1554-1586) was an English poet, scholar, soldier, and courtier, one of the most prominent figures at the court of Queen Elizabeth I of England (r. 1558-1603). During his lifetime, he was revered as the ideal Elizabethan gentleman and was viewed as a beacon of hope for Protestants in Europe, who dreamt of English involvement in a Protestant League. After his untimely battlefield death at the age of 31, his poems were published and became wildly popular, influencing the development of literature during the English Renaissance. His works include the pastoral poem Arcadia, the sonnet cycle Astrophel and Stella, and the essay The Defense of Poetry.

Early Life & Family

Philip Sidney was born in Penshurst Place in Kent, England, on 30 November 1554, the eldest son of Sir Henry Sidney and Lady Mary Dudley. His birth marked the end of a tempestuous time for the country and, indeed, for his own family. A little over a year before, his maternal grandfather, John Dudley, Duke of Northumberland (1506-1553), had been executed after his coup to install Lady Jane Grey (1537-1554) on the English throne ended in failure. In the wake of Northumberland's treason, his sons were attainted and imprisoned in the Tower of London – the youngest, Lord Guildford Dudley, was executed alongside Jane Grey, his wife, in February 1554, and the four others were condemned to die. Though related to the traitorous Dudleys by marriage, Sir Henry Sidney avoided their fate because his sisters were favorites of the new Queen Mary I of England (r. 1553-1558). Sir Henry secured his position further by cozying up to Queen Mary's consort, King Philip II of Spain (r. 1556-1598); it was partly because of this friendship that the surviving Dudley brothers were eventually pardoned and released. In his gratitude, Sir Henry named his firstborn after the Spanish king, who was also the boy's godfather.

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In May 1572, 18-year-old Sidney left England for a tour of the Continent, carrying a license from Queen Elizabeth.

In 1558, Queen Mary died, and her Protestant half-sister ascended the throne as Queen Elizabeth I. The rise of the new queen saw the Dudley family return to royal favor; one of Northumberland's sons, Robert Dudley, had been Elizabeth's close friend and, if rumors could be believed, her lover. In 1564, Dudley was created Earl of Leicester, with benefits extending to the rest of the family – Sir Henry Sidney was made Lord President of the Marches of Wales, and later, he was appointed Lord Deputy of Ireland, while his wife, Lady Mary Dudley, became one of the new queen's ladies-in-waiting. Lady Mary was often by Elizabeth's side, and when the queen fell dangerously ill with smallpox in October 1562, she helped nurse her back to health. Lady Mary contracted the disease herself, which greatly disfigured her face; thereafter, she was said to have always worn a mask when attending court to hide her scars, though this story may be apocryphal. Years later, Philip Sidney could have been thinking of his mother when writing his Certain Sonnets, four of which deal with a beautiful face disfigured by "the monster called Pain".

In October 1564, 9-year-old Philip was enrolled in Shrewsbury School, an excellent grammar school within the jurisdiction of his father's governance. A naturally studious boy, Sidney thrived at the school, mastering his studies of grammar, mathematics, rhetoric, Latin, French, and Greek, and grew into a handsome and athletic boy. Despite his fragile health, he was a talented horseman, fond of tilting at tournaments. After graduating from grammar school in 1568, Sidney enrolled at Christ Church College at Oxford, where he would study for the next three years. He stayed at Oxford under the guidance of his uncle, the Earl of Leicester, who introduced him to the queen. During this time, a marriage was proposed between Sidney and Anne Cecil, the daughter of one of England's most powerful families. However, the marriage was eventually broken off because Sidney's family was judged to be too poor, and the girl was married off to Edward de Vere, 17th Earl of Oxford, instead. In 1571, Sidney left college without finishing his degree.

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Travels

In May 1572, 18-year-old Sidney left England for a tour of the Continent, carrying a license from Queen Elizabeth that allowed "her trusty and well-beloved Philip Sidney, Esq., to go out of England into parts beyond the seas" (quoted in Poetry Foundation). He arrived in Paris in June, where he was welcomed by Sir Francis Walsingham (1532-1590), Elizabeth's ambassador to France. Sidney stayed in the French capital for the rest of the summer, partaking in the festivities that marked the signing of the Treaty of Blois, and befriending important officials like the Huguenot (Protestant) diplomat Hubert Languet (1518-1581). In early August, Sidney was even honored by King Charles IX of France (r. 1560-1574), who created him 'Baron de Sidenay'; however, since Elizabeth mistrusted foreign titles, Sidney never styled himself this way in England. The end of his stay in Paris was marked by the horrific events of the St. Bartholomew's Day Massacre, in which thousands of French Huguenots were slaughtered by Catholic mobs, the latest outbreak of violence in the ongoing French Wars of Religion (1562-1598). During the massacre, Sidney likely sheltered with Walsingham in the English embassy outside the city walls. Although he and Walsingham were Protestants, it is unlikely they were in any danger, as there is evidence that the French Catholics were careful not to harm English visitors.

Hubert Languet
Hubert Languet
Martin Bernigeroth (CC BY-NC-SA)

Sidney left France shortly thereafter and went to Frankfurt, where he was reunited with Languet, who had only narrowly escaped the bloodshed in Paris. The two men struck up a close friendship – Languet saw a lot of potential in the young man and likely hoped to use him as an instrument to advance the cause of Protestantism in Europe. As time wore on, Languet seems to have taken a personal interest in Sidney; their correspondence, written in Latin, contains hints of homoeroticism. In early 1573, Sidney stayed with Languet at his home in Vienna, before abruptly leaving to spend several months in Hungary; in a letter, Languet scolded his young companion for being away so long, writing: "When you left, you said that you would not be gone for more than three days. But now, like a bird that has forced its way through the bars of its cage, your delight makes you restless, flitting hither and yon, perhaps without a thought for your friends" (quoted in Poetry Foundation).

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In November 1573, Sidney arrived in Venice and spent most of the following year studying there and in Padua. In a 1574 letter, he promised to send Languet a portrait of himself "because this shows the sweet and long known love you have for me" and told his mentor that their friendship "puts in the shade all ordinary affections, as the sun with the lesser lights" (quoted in Duncan-Jones, 279). While in Venice, Sidney immersed himself in Italian culture to the point where Languet grew concerned that he might convert to Catholicism. In August 1574, he returned to Languet's house in Vienna, where he fell seriously ill. After recovering, he received a letter from his uncle Leicester, bidding him to hurry back to England. He arrived in London in May 1575 shortly after the tragic death of his 10-year-old sister Ambrosia.

Courtier

For the rest of the year, Sidney remained at court, serving as the queen's cupbearer; he reveled in the pageantry and festivities of court and often titled in the tournaments. During this time, he befriended powerful figures such as Walter Devereux, 1st Earl of Essex (1541-1576). Sidney accompanied Essex to Ireland in 1576; not long afterward, Essex contracted dysentery and died. On his deathbed, Essex announced his desire for his daughter, the 12-year-old Penelope, to marry Sidney when she came of age. "He is so wise, so virtuous, so goodly," the dying Essex said of Sidney, that "he will be as famous and worthy a gentleman as England ever bred" (quoted in Poetry Foundation). While in Ireland, Sidney helped his father – still serving as Lord Deputy – fight the Irish rebels. Thirsting for military glory, he even advocated an invasion of Catholic Spain, although this never materialized.

With his political ambitions frustrated, Sidney began to write poetry in earnest.

In February 1577, Sidney was sent as an emissary to the court of Rudolf II, Holy Roman Emperor (r. 1576-1612), his first political appointment. He met with several leading European Protestants, discussing the possibility of creating a Protestant League to combat Catholicism on the Continent; it was hoped that Sidney could leverage his influence with the queen to draw England into such an alliance. Upon returning to England, Sidney wrote a masque for the queen entitled The Lady of May to mark her visit to Leicester's estate in 1578. If this was meant to curry favor for her support of a Protestant League, it did not work; Elizabeth was hoping to pit Catholic Spain and France against one another, and did not want to risk upsetting her plans by forming an alliance of Protestant states.

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Sidney once again involved himself in politics in 1579, when he penned an open letter opposing a proposed marriage between the queen and the Catholic Duke of Alençon; such a match, Sidney feared, would invite civil war. Though the marriage never came to fruition, the letter brought Sidney into conflict with the Earl of Oxford, who had favored the marriage. Tempers between the two men, which were already high after Oxford had stolen Sidney's potential bride years earlier, boiled over during a tennis match, when Oxford ordered Sidney off his court, calling him a 'puppy'. Enraged, Sidney challenged Oxford to a duel, which was avoided only through the intervention of the queen herself. After this fiasco, Sidney retired from court for a year, spending most of his time at his sister's home in Wilton. It was during this withdrawal, his political ambitions frustrated, that Sidney began to write poetry in earnest.

Works

It is likely that Sidney never intended his poetry to be published; indeed, in the opening of his pastoral poem Arcadia, he asserts that it was only written to entertain his sister Mary Herbert, Countess of Pembroke (hence the poem's full title The Countess of Pembroke's Arcadia). He probably began writing Arcadia in 1580 – the work follows two young noblemen, Musidorus and Pyrocles, in their romantic adventures across the Arcadian countryside, conveying themes of love, chivalry, and virtue. Comprised of some 180,000 words, the poem is by far Sidney's most ambitious work; in 1583, he would totally revise it, creating a new version (the versions are distinguished from one another by the titles Old Arcadia and New Arcadia). Published posthumously in 1590, Arcadia would prove immensely popular and would spark a fad for pastoral poetry; Elizabethan poets inspired by this work include Robert Greene, Thomas Lodge, and, most notably, William Shakespeare (1564-1616), whose comedy As You Like It was written in the style popularized by Arcadia.

Penelope Devereux, Lady Rich
Penelope Devereux, Lady Rich
Nicholas Hilliard (Public Domain)

In 1581, Sidney returned to court where he was reintroduced to Penelope Devereux, Essex's daughter to whom he had once been betrothed. Now 18, Penelope was soon regarded as the most beautiful woman at court, and Sidney fell passionately in love with her. But despite previous promises, their romance was never to be; in March, Penelope was married to Baron Robert Rich (later the Earl of Warwick), seemingly against her will. Their marriage proved unhappy, and Sidney seems to have loved Penelope for the rest of his life. In his sonnet sequence Astrophil and Stella (1582), the character of Stella is widely believed to have been based on Penelope; indeed, the sequence recounts a courtier's passion for a woman he cannot have, ending in his abandonment of his suit in order to devote himself to the 'great cause' of public service. Written in the Petrarchan rhyme scheme, this sonnet sequence was likely circulated in manuscript form prior to Sidney's death, meaning Penelope probably read them. The first sonnet in the sequence remains one of the best-known of Sidney's poems:

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Loving in truth, and fain in verse my love to show,

That she, my dear, might take some pleasure of my pain,

Pleasure might cause her read, reading might make her know,

Knowledge might pity win, and pity grace obtain,

I sought fit words to paint the blackest face of woe:

Studying inventions fine, her wits to entertain,

Oft turning others' leaves, to see if thence would flow

Some fresh and fruitful showers upon my sunburned brain.

But words came halting forth, wanting Invention's stay;

Invention, Nature's child, fled stepdame Study's blows;

And others' feet still seemed but strangers in my way.

Thus, great with child to speak, and helpless in my throes,

Biting my truant pen, beating myself for spite:

"Fool," said my Muse to me, "look in thy heart, and write!"

Sidney's sonnets, which often dripped with melancholy and put love on a pedestal, were published in 1591 when sonnet-writing was much in vogue; his sonnets are often regarded as among the greatest of the era, behind only those of Shakespeare. His final major work was a critical essay, The Defense of Poetry (circa 1583), in which he elegantly argues that poetry combines the liveliness of history with the ethical focus of philosophy and is therefore more effective at bringing its readers to virtue than either of the aforementioned disciplines. Sidney's essay became a key piece of Elizabethan literary criticism and inspired such poets as Edmund Spenser (1552-1599), who was friends with Sidney. Along with these major works, Sidney composed other poems and translations of Psalms.

Later Years & Military Endeavor

As he continued to write, Sidney still hungered for glory and longed for an important post from the queen. Unfortunately, most of his duties around this time were purely ceremonial. In January 1583, he was knighted, but only to give him the necessary qualifications to stand in for a friend, Prince Casimir, who was being inducted into the Order of the Garter but was unable to attend the ceremony. In September, he married Frances Walsingham, the daughter of Sir Francis Walsingham, who was now the queen's secretary of state; certainly, Sidney hoped the marriage would improve his chances of advancement at court. The couple had one daughter, named Elizabeth after the queen. In 1584, he was elected to Parliament from Kent, beginning what promised to be a bright political career.

But then, trouble began to brew in the Netherlands. In July 1584, William the Silent, Prince of Orange (r. 1544-1584), was assassinated, shortly after being branded an outlaw by the King of Spain. When war broke out between the Protestant Dutch rebels and the Catholic Spanish, Queen Elizabeth decided to intervene on the side of the Dutch. In December 1585, she sent an army to the Low Countries under the command of Sidney's uncle, Robert Dudley, 1st Earl of Leicester. Sidney, jumping at the opportunity to finally win some martial glory, was given command of the English garrison at Flushing (Vlissingen). Sidney saw no combat but was hard-pressed to maintain the morale of his poorly supplied troops; in early 1586, he wrote to his father-in-law that while his own resolution was steadfast, his soldiers were likely to desert if the queen did not pay them soon. While he was in Flushing, Sidney received tragic news; his father, Sir Henry, died in May 1586, and Lady Mary three months later.

The Fatal Wounding of Sir Philip Sidney
The Fatal Wounding of Sir Philip Sidney
Benjamin West (Public Domain)

Death & Legacy

In June 1586, Sidney got his first taste of action when he led a daring nighttime raid on Spanish forces near the city of Axel. In September, Leicester's army began laying siege to Zutphen, a town of great strategic significance to the Spanish; upon learning that the Spanish were sending a well-guarded baggage train to Zutphen to relieve the garrison, Leicester decided to set an ambush, which Sidney volunteered to lead. At the Battle of Zutphen (22 September 1586), Sidney attacked the baggage train and led his men in three charges against the enemy lines. According to legend, he noticed that his men were poorly armored – in order to encourage them forward, Sidney stripped off his own armor before leading the third charge. This proved to be a fatal decision, as his thigh was shattered by a musket ball. The wounded Sidney was taken off the battlefield; according to another story, he had called for water before noticing another soldier who was wounded even worse than he was. As chivalric as ever, Sidney gave his water to the other man, telling him, "Thy necessity is yet greater than mine." Sidney's wound turned gangrenous, and he died 26 days later on 17 October 1586, at the age of 31.

His body was returned to England and interred in Old St. Paul's Cathedral in February 1587; he was lauded as a military hero, and his funeral procession nearly bankrupted Sir Francis Walsingham, who paid for it. Sidney was already regarded as the ideal Elizabethan gentleman, but the publication of his poems in the 1590s cemented his legacy as one of the era's greatest poets; his works popularized the pastoral genre and contributed to the sonnet trend, and he influenced most of the great Elizabethan dramatists that came afterward, including Robert Greene, Edmund Spenser, and, of course, William Shakespeare. Though he is less known today than many of his contemporaries, Sidney was undoubtedly one of the most important Elizabethan poets, who helped shape the course of English Renaissance literature.

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About the Author

Harrison W. Mark
Harrison Mark is a graduate of SUNY Oswego, where he studied history and political science.

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Questions & Answers

Who was Sir Philip Sidney?

Sir Philip Sidney (1554-1586) was an English poet, scholar, soldier, and courtier, who wrote some of the most influential poetry of the Elizabethan Era. He was also noted as the ideal Elizabethan courtier.

What were Sir Philip Sidney's major works?

Sir Philip Sidney's major works include his pastoral poem 'Arcadia', his sonnet sequence 'Astrophel and Stella', and his critical essay 'The Defense of Poetry'. All of these works were published posthumously but became wildly popular in the 1590s.

How did Sir Philip Sidney die?

Sir Philip Sidney was mortally wounded while leading a charge against the Spanish at the Battle of Zutphen and died 26 days later on 17 October 1586.

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Mark, H. W. (2025, May 29). Philip Sidney. World History Encyclopedia. Retrieved from https://www.worldhistory.org/Philip_Sidney/

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