Like Lord Southampton, Lord Pembroke, and others in the reign of Queen Elizabeth, Sir William always maintained a company of stage players to present masques and plays on festivals and days of solemnity, the actors, when the play was ended, always praying (as the custom was) for the Queen's Majesty, the Council, and our worshipful good master Sir William Holles.1 On the anniversary of this time of rejoicing one may see with the mind's eye, or read in Spenser’s Fairy Queen, of such a scene, which none could describe so well as “the prince of poets,” who was a contemporary of Sir William’s, and may himself have been present on some one or other of these occasions, when the good knight was seated in state, surrounded by his family and chosen friends, on a raised dais in the centre of the great hall, where—

...“round about the walls yclothed were
With goodly arras of great majesty,
Woven with gold and silk so close and rare
That the rich metal lurked privily,
As feigning to be hid from envious eye”—

while on the floor his dependents and poorer neighbours were grouped around watching the performance by his band of players of some story of Robin Hood, a play by Nash or Kyd, or, perchance, looking with loud merriment at the rude gambols of the hobby-horse, or should it be in the latter days of the good Lord of Haughton, he might be delighting his friends with one of Marlowe’s stirring plays.

Good natured as he was, there was ever within the breast of the worthy knight a firm determination never to be anything less than the head of his own family. His daughter Gertrude, of whom mention has been made, is said to have possessed great personal attractions, and was sought in marriage by Lord Clifford, afterwards Earl of Cumberland, but to this proposal Sir William's consent could not be obtained. His friends, anxious that he should reconsider his decision, suggested the great advancement it would be to the young lady to be matched with one so high in position. To this he answered with his usual exclamation: “Sake of God! I do not like to stand with my cap in hand to my son-in-law; no, I will see her matched to an honest gentleman with whom I may have friendship and conversation.” This resolution he carried out; she married Mr. Walter Stanley, a gentleman of great worth and merit, a younger son of the Earl of Derby.2

Scarcely any occasion could prevent his attendance at religious worship. Twice every day, even to his last illness, he would proceed with his whole family across the river to his chapel, which stood at some distance from the house, to hear divine service celebrated according to the liturgy of the Church of England. Gervase Holles sums up his account of Sir William by saying: “This love to God’s House he bore with him to his grave, making it his last care, and leaving it his first charge in his will, to his heirs, ‘forever to uphold, repair, and maintain the said chapel, as oft as need shall require,’ which, how well it hath been performed, I grieve to think, it being left wholly ruinous; a habitation to which nothing but bats and owls repair.”

Sir William died on the 18th of January, 1590. His eldest son, who was named Denzil, married Eleanor, daughter of Edmund, Lord Sheffield, and was settled at Irby in Lincolnshire. He died about nine months before his father; the estates consequently passed to John Holles, his eldest son, who, from the account given by his biographer, must when a child have shown great precocity in learning, for when he had barely attained his thirteenth year he was sent by his father to Cambridge, “and on the Master of the College posing him in grammar and Greek, he received such unexpected satisfaction to every question that he caught the boy up in his arms, and kissing him, said to those who were by:  ‘This  child, if he lives, will prove a singular honour and ornament to this kingdom.’”

From the University he was sent to Gray’s Inn, that by the study of the law he might fit himself for the service of the Commonwealth, and there he remained for some years. He then served as a volunteer in the war in the Netherlands under his kinsman Sir Francis Vere, and was also in the famous sea fight against the Spanish Armada. He had the honour to be chosen by Queen Elizabeth one of the company of Gentlemen Pensioners.

But when he attained the age of twenty-six years this fair inheritance devolved upon him, together with the care of several brothers and sisters. His two brothers were sent to the University, and from there the elder, Sir George, and afterwards the younger brother, Thomas, joined the army in the Netherlands.

Though Holles proved himself in many respects well qualified to advance the fortunes of the family, he was of a restless, adventurous disposition, and owing to his quarrelsome nature was often embroiled, even with some of the most eminent of his contemporaries. Four months after he inherited the estate he married Anne, daughter of Sir Thomas Stanhope, of Shelford, in Nottinghamshire. By her he had six sons, only two of whom came to maturity, and four daughters. This marriage, although it brought him all the happiness that could be hoped for in a wife, led to deep and lasting animosity with his great neighbour Gilbert, Earl of Shrewsbury, the son of his grandfather's especial friend. It was on the occasion of the christening of his second son, Denzil Holles (afterwards Lord Holles of Ifield), at Haughton, that a duel occurred between Sir John Holles and Gervase Markham, when the neighbourhood was raised in arms.3

It appears to have been in some measure owing to the many powerful enemies who were incensed by his conduct that Holles spent a great part of several years after his marriage in travel and military adventure. He served under the Lord Deputy Sir William Fitzwilliam, in Ireland, where he so greatly distinguished himself against the rebels that he received the honour of knighthood. For about two other years he was in Hungary fighting against the Turks, and travelling in France and Italy. His last military expedition was made under the Earl of Essex to the Terceras in 1597

1 Gervase Holles.
2 Gervase Holles.
3 An account of this quarrel, which took place in Sherwood  Forest between Sir John Holles, afterwards first Earl of Clare, and one Gervase Markham, a distant connection of the Markhams of Gotham and Ollerton, although not the celebrated writer of that name, is of some interest.
“It seems there had been a treaty between the old Earl of Shrewsbury and Sir William Holles, concerning a marriage between his grandson John and a kinswoman of the Earl. To which motion, whether he meant it in earnest or pretending it only for fear of displeasing his grandfather, he seemed not unwilling, so that every one thought that he would have proceeded. But after the decease of them both (for George, Earl of Shrewsbury, and Sir William Holles died in the same year), liking Mrs. Stanhope better, he married her, and relinquished the Earl’s kinswoman.
“This the Earl took as the greatest affront, the rather because Sir Thomas Stanhope and the Earl were great enemies. The process of this difference caused a great deal of trouble and some loss of life; for first Roger Orme, who was then Sir John Holles’ servant, though afterwards a captain in Ireland and the Low Countries, fought a duel with one Pudsey, gentleman of the horse to the Earl of Shrewsbury, in which Pudsey was slain. And this quarrel arose upon the ground of the difference between their masters. The Earl eagerly prosecuted Orme’s life, but Sir John Holles got him conveyed to Ireland, and maugre the Earl’s power, procured his pardon of Queen Elizabeth.
“Upon Orme’s business followed that of his own with Gervase Markham, so much talked of yet in these parts. Gervase Markham was a great confidant of the Countess of Shrewsbury, and was usually in those days termed her champion. A proper handsome gentleman he was, and of great courage. He, after Pudsey was slain, let fall some passionate words accusing Sir John Holles as the cause of that quarrel, and as being guilty of his death. This coming to the ears of Sir John, he sends him a cartel to this effect:—
“‘For Gervase Markham,—Whereas you have said that I was guilty of that villainy of Orme, in the death of Pudsey; I affirm that you lie, and lie like a villain, which I shall be ready to make good upon yourself, or upon any gentleman my equal. John Holles.’
“Markham returned for answer that he accepted ‘the challenge, and would accordingly give a meeting at such an hour alone, or with either of them a boy of fourteen or under, the place, Worksop Park, and the weapons, rapier and dagger.’ Sir John Holles, allowing of the other circumstances, excepted against the place, being the park where his mortal enemy, the Earl of Shrewsbury, then lived, which he thought neither reasonable for himself to admit, nor honourable for his enemy to propose, and therefore urged that a more equal place be assigned. Markham taking advantage of this, as if he declined the encounter, published it accordingly to his disgrace. Finding this unworthy dealing, Sir John Holles resolved to take that opportunity which fortune should next offer him; and such a one shortly offered him, on the following occasion. To the christening of his second son, Denzil Holles, the Lady Stanhope, his mother-in-law, was invited as godmother, after which performed she returned from Haughton to Shelford, and Sir John Holles accompanying her part of the way over the forest of Sherwood, it fortuned that Gervase Markham and others in his company met them and passed by. So soon as he saw that Markham was passed, he took leave of the Lady Stanhope, galloped after and overtook him, when, observing how unworthily he had dealt with him, they both alighted and drew their rapiers. I have heard him say that upon the first encounter he used these words: ‘Markham, guard yourself better, or I shall spoil you presently’ (for he said he laid as open to him as a child); and the next pass he run him through the middle of the guts up to the hilt, and out behind towards the small of the back. With this wound Markham fell, and was carried off the ground by those in his company, while Sir John Holles with his servant Ashton, and a groom, who only were with him, returned to Haughton. The news coming to the Earl of Shrewsbury, he immediately raised his servants and tenants to the number of one hundred and twenty, with a resolution to apprehend Sir John Holles as soon as he should know that Markham’s wound was fatal; which Edmund, Lord Sheffield, afterwards Earl of Mulgrave, understanding, he speedily repaired to Haughton, with three score in his retinue out of Lincolnshire, to assist his cousin-german in case the Earl should attempt anything. ... ‘I hear cousin,’ says Lord Sheffield, ‘that my Lord of Shrewsbury is prepared to trouble you; take my word, before he carry you, it shall cost many a broken pate;’ and he went in and remained at Haughton until they had certain account that Markham was past danger; who indeed recovered, and lived after to be an old man.”
Twenty-eight years after this duel, another incident occurred which brought Sir John (then Earl of Clare) and Gervase Markham into contact. Gervase Markham, being then Sheriff of Nottingham, was robbed of about £5,000 during his absence from home, by two of the Soubyes and others. But pursuit being made after them, they hid about £2,000 of the money in Gamelston Woods (a lordship of the Earl of Clare’s), which was found, and brought to the Earl as lord of the fee, to whom as felon’s goods, it escheated: but he presently sent the whole back to Gervase Markham, from whom it was stolen; scorning to advantage himself by the spoils of his enemy. This act more enraged Markham than the loss of his money, because it imposed upon himself an obligation to his adversary. Yet, after he had curst and sworn like a beggar, he enforced upon himself so good manners as to come to the Earl at Haughton to give him thanks, which, from the time of their combat, was the only occasion during their lives that they had seen one another (Gervase Holles, quoted by Collins).