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William Shakespeare (baptized April 26, 1564, died April 23, 1616) is arguably the greatest writer in any language. Shakespeare’s classical poetry is not only one of the most exalted examples of what an immortal sense of creative identity can accomplish, it is a symbol of the artist’s immortality, and timelessness itself. As today’s coronavirus crisis brings the question of our mortality to the forefront of daily life, let us use this crisis as an opportunity to reflect upon a question even more daunting than our mortality, our immortality.

Shakespeare’s 154 sonnet cycle offers us one of the most intimate, rigorous and intense accounts of an individual’s journey to immortality. Given the richness and the density of ideas found in the cycle, the author has attempted to compile a list of Shakespeare’s 10 greatest sonnets. While myriad websites list a “top 10” of Shakespeare’s sonnets, and no two lists are likely the same, picking 10 of the poet’s greatest sonnets requires selecting those which reveal the higher order of meaning woven through the series as a whole—the higher hypothesis underlying each individual piece. It means selecting those sonnets which best capture the depths of Shakespeare’s insight into the nature of man, and also the skill with which he is able to demonstrate this insight. It also means considering what is often overlooked by popular or academic readings of Shakespeare.

Too often, Shakespeare readings are weighed down by over-romanticized or sentimental readings, or by narrow academic analysis which tends to focus on the sonnets as isolated pieces. The result is that each sonnet loses the shadow of a higher idea that Shakespeare communicates.

This list does not take up the sonnets in numerical order, but instead chooses the sonnets that best convey the higher order of meaning governing the entire cycle. We will identify specific recurring themes and subjects, and their developing relationships at key moments in the cycle. In this way, we will map out the principle governing the whole—just like a star that governs the orbits of all its planets and their moons.

10. Sonnet #1
From fairest creatures we desire increase,
That thereby beauty’s rose might never die,
But as the riper should by time decease,
His tender heir might bear his memory:
But thou contracted to thine own bright eyes,
Feed’st thy light’s flame with self-substantial fuel,
Making a famine where abundance lies,
Thy self thy foe, to thy sweet self too cruel:
Thou that art now the world’s fresh ornament,
And only herald to the gaudy spring,
Within thine own bud buriest thy content,
And, tender churl, mak’st waste in niggarding:
Pity the world, or else this glutton be,
To eat the world’s due, by the grave and thee.

In Sonnet I, Shakespeare begins by speaking to all those people who are persuaded that beauty is only skin deep. From the first two lines, he says skin-deep beauty fades, that even the fairest of creatures is no match for time. We are all attracted to beauty and long for it, “from fairest creatures we desire increase,” to reproduce, yet in recognizing that this kind of beauty fades, Shakespeare prepares us to discover an even higher order of beauty: the power to create new beauty! Herein lays the germ of Shakespeare’s entire theme as he develops it throughout the series. He warns us that to be preoccupied with our own beauty is to be blind to this higher order of beauty, which lies in the future.

Thus from the outset, Shakespeare confronts us with the question of beauty, mortality and the contemplation of what comes after us. He begins with this question because he knows that it is the only way in which we can be brought to contemplating a higher idea: our immortality.

9. Sonnet #130
My mistress’ eyes are nothing like the sun;
Coral is far more red, than her lips red:
If snow be white, why then her breasts are dun;
If hairs be wires, black wires grow on her head.
I have seen roses damasked, red and white,
But no such roses see I in her cheeks;
And in some perfumes is there more delight
Than in the breath that from my mistress reeks.
I love to hear her speak, yet well I know
That music hath a far more pleasing sound:
I grant I never saw a goddess go,
My mistress, when she walks, treads on the ground:
And yet by heaven, I think my love as rare,
As any she belied with false compare.

By turning hyperbole on its head, Shakespeare develops a metaphor that allows us to contemplate a completely different quality of beauty, one that goes beyond simple sense perception. Shakespeare is going beyond the tendency of many Romantic poets who too often (not always) contented themselves with simply titillating the senses and reveling in a thousand pretty images of nature or of the beloved—Shakespeare’s love resides in a higher realm.

How might this higher realm be attained?

8. Sonnet #17

The creation of beauty, as opposed to obsession with one’s own beauty as some fixed thing, becomes a self-developing process. It becomes the higher hypothesis of our existence. This theme is thoroughly developed from sonnets 1through 16, but in sonnet 17, something begins to happen—there is a singularity, a change, regarding the hypothesis that came before:

Who will believe my verse in time to come,
If it were filled with your most high deserts?
Though yet heaven knows it is but as a tomb
Which hides your life, and shows not half your parts.
If I could write the beauty of your eyes,
And in fresh numbers number all your graces,
The age to come would say ‘This poet lies;
Such heavenly touches ne’er touched earthly faces.’
So should my papers, yellowed with their age,
Be scorned, like old men of less truth than tongue,
And your true rights be termed a poet’s rage
And stretched metre of an antique song:
But were some child of yours alive that time,
You should live twice, in it, and in my rhyme.

Despite procreation, Shakespeare fears that beauty may still not survive, or that he wishes he could better protect it against time. Thus, Shakespeare introduces a new element into the process of generating beauty, saying “But were some child of yours alive that time / You should live twice, in it, and in my rhyme.” We are now witnessing a doubly connected hypothesis where the creation of beauty becomes twofold. There is another level he is defining here, a higher level of cardinality, where art itself plays a role. It is a theme that John Keats would later take up and develop to new heights with his “Ode on a Grecian Urn.”[1] We will come back to the sonnets following #17 later in the list.

7. Sonnet 116
Let me not to the marriage of true minds
Admit impediments. Love is not love
Which alters when it alteration finds,
Or bends with the remover to remove:
O, no! it is an ever-fixed mark,
That looks on tempests and is never shaken;
It is the star to every wandering bark,
Whose worth’s unknown, although his height be taken.
Love’s not Time’s fool, though rosy lips and cheeks
Within his bending sickle’s compass come;
Love alters not with his brief hours and weeks,
But bears it out even to the edge of doom.
If this be error and upon me proved,
I never writ, nor no man ever loved.

Sonnet 116 is often read at weddings and considered the quintessential poem on love and marriage. It develops the idea of love as something that transcends time and space. Man and woman, through love, assume a kind of strength which is un-vanquishable and can in a certain way overcome all elements. Love in this sense partakes in the Eternal, the One, and so through love, we also may participate in that Eternal, that One. As Shakespeare says:

Love’s not Time’s fool, though rosy lips and cheeks
Within his bending sickle’s compass come;

However, he starts the sonnet by saying something rather peculiar for the discerning reader:

Let me not to the marriage of true minds
Admit impediments.

The significance becomes much clearer in a proper recitation, where one is challenged to communicate the intent of the first two lines: Why would Shakespeare be an impediment to the marriage of true minds? Which minds is he referring to? If we don’t confine ourselves simply to sonnet 116, but also read the preceding sonnet, and the one that follows, a richer and more complex sense of irony becomes possible. As we shall see, some relatively new scholarship may help to shed light on some of the questions that arise when trying to communicate the genuine intent and sense of the individual lines.

While some might insist it doesn’t matter, and that the sonnet can be read standing alone, without knowing its circumstances and meanings, in this case, with relatively new scholarship that identifies Shakespeare’s “Dark Lady,” (found in sonnets 127-154) we have the possibility of accounting for the ambiguity mentioned above (and many others). The conclusion would give the sonnet a real biting irony.

Hildegard Ham­mer­­schmidt-Hum­mel, a German Shakespeare scholar, known for exceptionally scrupulous rigor in her scholarly work, bringing together elements of literary scholarship, iconography, forensic sciences, along with the use of botanical and medical expertise, put forward the hypothesis that this dark lady is none other than Elizabeth Vernon, the wife of Henry Wriothesley, the Earl of Southampton.[2] Only ten weeks after her marriage, Elizabeth gave birth to a girl.

Dr. Ham­mer­­schmidt-Hum­mel goes through some rather compelling evidence, using portraits from that time, including a famous one known as “The Persian Lady,” along with a previously lost sonnet (which she argues is the last and final sonnet in Shakespeare’s series) and inscriptions from the portrait. In terms of all the possible people Shakespeare might have been addressing (accounting for Shakespeare’s connection to the Earl of Southampton), she concludes that this child was most likely Shakespeare’s daughter. It would also explain certain intrigues around that time.

It is not our purpose to try and convince people of these findings. That being said, availing ourselves of such a hypothesis to situate the context of this later series and account for the irony at the beginning of sonnet 116 proves to be surprisingly useful. It helps us picture the possibilities and scenarios which speak to the kinds of sub-narratives Shakespeare explicitly refers to throughout many of the sonnets in the series. Moreover, it gives meaning to the two opening lines, which we’re otherwise forced to believe are just some superfluous rhetorical device that otherwise has nothing to do with the rest of the sonnet. In case Hammerschmidt-Hummel’s hypothesis is relatively correct, then sonnet 116 becomes a formidable example of that biting irony which is so characteristic of the Bard.

Any reader should at least give the sonnet a genuine reading aloud and try to play around with the different possibilities involved in its recitation. In this light, it becomes interesting to follow this sonnet with 117:

Book both my wilfulness and errors down,
And on just proof surmise accumulate;
Bring me within the level of your frown,
But shoot not at me in your wakened hate;
Since my appeal says I did strive to prove
The constancy and virtue of your love.

– Sonnet 117

In sonnet 116, Shakespeare asserts the constancy and eternal nature of love. However, he opens ironically with “let me not an impediment to true minds be” as if he were a potential obstacle to the proof of such love, i.e. Elizabeth Vernon and the Earl of Southhampton. In the following sonnet 117, he speaks of having tried to prove the constancy of the lady he addresses. In sonnet 115, Shakespeare speaks of love being “a babe” and suggests giving “full growth to that which still doth grow.”

Is Shakespeare addressing the woman he loves—the woman pregnant with his child—who has chosen to marry someone else, the Earl of Southhampton? Many theories about the meaning of such lines could be proposed, but as in scientific work where the effects and intended consequences of a given hypothesis can be put to an experimental test, here, the hypothesis for these sonnets can be tested through a live recitation. One does not have the luxury of simply reading the piece, one must know what they are reading, and make the intention verbally transparent. Dr. Hammerschmidt’s hypothesis proves exceptionally helpful in providing context for what we are reciting and it gives these sonnets an ironic richness which is so characteristic of Shakespeare.

6. Sonnet #129

By sonnet 129, the declarations on the nature of love, constancy, have been left behind as the theme of the “Dark Lady” is advanced. In 129, we have a denunciation of lust, its effects:

The expense of spirit in a waste of shame
Is lust in action: and till action, lust
Is perjured, murderous, bloody, full of blame,
Savage, extreme, rude, cruel, not to trust;
Enjoyed no sooner but despised straight;
Past reason hunted; and no sooner had,
Past reason hated, as a swallowed bait,
On purpose laid to make the taker mad.
Mad in pursuit and in possession so;
Had, having, and in quest to have extreme;
A bliss in proof, and proved, a very woe;
Before, a joy proposed; behind a dream.
All this the world well knows; yet none knows well
To shun the heaven that leads men to this hell.

Shakespeare is reflecting on the conflicting battle of infatuation with beauty, the feeling of being enthralled by it, and the strong desire to “possess” it as though it were some object he wishes to claim. The woman he loves has perhaps chosen another course for her life, but he cannot seem to let go (whether the Elizabeth Vernon narrative be entirely accurate or not); he is conflicted with the different feelings of desire, fear, loss. He is sharing all this with us. He is an open book, and in saying all this he is warning the reader to look beyond his immediate feelings, his impulses, no matter how noble they may seem—not be so blind as to not recognize “the heaven that leads men to this Hell.”

Thus the struggle with sense perception, and of overcoming even the greatest sense of power which our unbridled feelings might have, leads us to the contemplation of mind and its role in true happiness. Whether the Hammerschmidt’s Elizabeth Vernon hypothesis is fully correct or not, it is in this case secondary to understanding the sonnet in its context, however it does help to serve as a kind of predicate, or device by which to imagine the sort of circumstances under which this kind of series of hypotheses and of conflicting emotions might have arisen. It also helps to humanize Shakespeare, and helps us to not be so vain as to imagine some great individual above all human folly and error.

In our estimation, it is not deprecatory to speculate on these kinds of issues about Shakespeare. Instead, it is all the more complimentary to consider that such a human being, who struggled with many of the complexities of life which many of our fellow human beings struggle with, was yet able to overcome himself, through his commitment to creativity, and ascend to awesome heights as the immortal bard. This series is the record of his journey.

See sonnets 147-150 for a full depiction of the battle between sense and mind, between the commitment to truth and love, and the deceptions of lust and ego—

Oh me, what eyes hath Love put in my head
Which have no correspondence with true sight!
– Sonnet 148

5. Sonnet #55
Not marble, nor the gilded monuments
Of princes, shall outlive this powerful rhyme;
But you shall shine more bright in these contents
Than unswept stone, besmear’d with sluttish time.
When wasteful war shall statues overturn,
And broils root out the work of masonry,
Nor Mars his sword, nor war’s quick fire shall burn
The living record of your memory.
‘Gainst death, and all oblivious enmity
Shall you pace forth; your praise shall still find room
Even in the eyes of all posterity
That wear this world out to the ending doom.
So, till the judgment that yourself arise,
You live in this, and dwell in lovers’ eyes.

In Sonnet 55, Shakespeare asserts the primacy of his poetic power as a force that defies a purely mortal nature—it is immortal. In the context of epic historical changes, of harrowing battles and of the crashing down of monuments, through a sweeping depiction of the vicissitudes of life, despite this, Shakespeare’s rhyme partakes of something higher, which these monuments, these stones, these princes cannot, because they do not possess creativity.

Of all the subjects he chooses to write about, he chooses love, and as a show of his love, his rhyme becomes the vehicle by which to immortalize it. On a higher level, this also demonstrates the power of love itself, of Agape—selfless love—and of love for mankind, which is that force which moves one to create that which overcomes all worldly obstacles.

4. Sonnet #18
Shall I compare thee to a summer’s day?
Thou art more lovely and more temperate:
Rough winds do shake the darling buds of May,
And summer’s lease hath all too short a date:
Sometime too hot the eye of heaven shines,
And often is his gold complexion dimmed,
And every fair from fair sometime declines,
By chance, or nature’s changing course untrimmed:
But thy eternal summer shall not fade,
Nor lose possession of that fair thou ow’st,
Nor shall death brag thou wander’st in his shade,
When in eternal lines to time thou grow’st,
So long as men can breathe, or eyes can see,
So long lives this, and this gives life to thee.

Arguably the most famous in the sonnet cycle, Shakespeare makes a series of comparisons whose power lies in their delicate treatment. He starts by asking whether he should compare his love to a summer day and gives reasons for why his love trumps such comparison, “rough winds do shake the darling buds of May,” “sometimes too hot the eye of heaven shines.” While there is great beauty in each image, there is also a sense of limitation. Each image alludes to the imperfections of the material world, of our mortality. We are left more vulnerable and open to the idea of our own fragile nature, but it is in precisely that vulnerability that we are compelled to seek that which lasts, that which allows us to transcend our delicate mortal coil.

3. Sonnet #59
If there be nothing new, but that which is
Hath been before, how are our brains beguil’d,
Which labouring for invention bear amiss
The second burthen of a former child.
Oh that record could with a backward look,
Even of five hundred courses of the sun,
Show me your image in some antique book,
Since mind at first in character was done,
That I might see what the old world could say
To this composed wonder of your frame;
Whether we are mended, or where better they,
Or whether revolution be the same.
Oh sure I am the wits of former days,
To subjects worse have given admiring praise.

Shakespeare here contemplates the possibility of knowing whether something as beautiful as his love has not already been written? Right from the beginning, he alludes to the biblical phrase, “there is no new thing under the sun” (Ecclesiastes 1:9), creating a sort of crisis. Are his efforts in vain? If only he had a way to “prove” his love is different. Yet he concludes, as an artist, a creator, he is in a very real sense a “co-creator”: “Oh sure I am the wits of former days / To subjects worse have given admiring praise.” Shakespeare stands at the point of a new Renaissance, he stands in the shadow of classical Greece, and in the shadow of the Italians whose sonetto form he has fitted to the English language in order to communicate a new paradigm of “profound ideas concerning man and nature.” However, like many of the sonnets, they often come in pairs, like paired electrons or diatomic molecules, and here 59 is one which serves to set up the next one:

2. Sonnet #60
Like as the waves make towards the pebbled shore,
So do our minutes hasten to their end;
Each changing place with that which goes before,
In sequent toil all forwards do contend.
Nativity, once in the main of light,
Crawls to maturity, wherewith being crown’d,
Crooked eclipses ‘gainst his glory fight,
And Time that gave doth now his gift confound.
Time doth transfix the flourish set on youth
And delves the parallels in beauty’s brow,
Feeds on the rarities of nature’s truth,
And nothing stands but for his scythe to mow:
And yet to times in hope, my verse shall stand
Praising thy worth, despite his cruel hand.

In this counterpart to sonnet 59, Shakespeare asserts the primacy of the artist, of the creative mind, and his ability to create something “new under the sun.” This becomes fundamental for recognizing Shakespeare’s acknowledgement of where he stands in history, that despite 500 courses of the sun, he is creating something new. Moreover, not only is he creating something new, but he is actually redefining the directionality of clock time, where rather than fade with the passing of time. In times to come, his “verse shall stand/Praising thy worth, despite his cruel hand.” In fact, not only would it stand, it would increase in greatness; rather than wear his rhyme out, each 500 new courses of the sun has increased its worth, by 500 courses of the sun. Thus Time increases its worth! This is true immortality, in which every individual human being may partake.

1. Sonnet #65
Since brass, nor stone, nor earth, nor boundless sea,
But sad mortality o’ersways their power,
How with this rage shall beauty hold a plea,
Whose action is no stronger than a flower?
O! how shall summer’s honey breath hold out,
Against the wrackful siege of battering days,
When rocks impregnable are not so stout,
Nor gates of steel so strong but Time decays?
O fearful meditation! where, alack,
Shall Time’s best jewel from Time’s chest lie hid?
Or what strong hand can hold his swift foot back?
Or who his spoil of beauty can forbid?
O! none, unless this miracle have might,
That in black ink my love may still shine bright.

Here the balance of historical time, clock time, is counter-posed with the most delicate images: how can such things hold a plea, when even the greatest of monuments must yield to time? This is a question all mortals must ask in contemplating the purpose of their lives.

In this sonnet, along with sonnet 18, one sees how Shakespeare uses the most fragile images, those most vulnerable to the indiscriminate blows of fate and nature, ironically, to move us in the most powerful of ways, because they invoke in us the greatest sense of humanity. In having gone through a series of hypotheses, from physical beauty, the belief in sense perceptions, the trappings of lust and the gluttony of Time; having considered the crashing down of monuments, the fortunes of princes, a legacy carried on by offspring, the vicissitudes of mortality and our desire for all things that must ultimately flee, we are yet compelled to ask: “how shall beauty hold a plea?” This becomes the most important question; what great agency, what saving grace, what power, can overcome time?

O! none, unless this miracle have might,
That in black ink my love may still shine bright.

The power of Love and creativity combined are the force, which can in a very real sense move mountains, and have the power to accomplish that which seems impossible. Were Shakespeare just another skilled versifier, moved by nothing other than his wish to titillate our senses with finely written lines and relish in a thousand beautiful images of his beloved, his poetry would have none of the power it has today. The reason for this is simple:

Though I speak with the tongues of men and of angels, and have not charity, I am become as sounding brass, or a tinkling cymbal.

– Corinthians 1:13

Shakespeare understood this in its most profound sense.


Shakespeare’s work is not some sentimental romanticizing of his love; nor is it really a love of an individual in the strict sense of the word; just as Petrarch’s Laura (meaning “laurel”) and Dante’s Beatrice (meaning “she who blesses”), they are archetypes, predicates, by which to elaborate a qualitatively higher conception of love which is truly universal, i.e. Agape. Though this love can be expressed towards another individual, the difference is Shakespeare is not coming from a place of Eros, of wanting to possess such a love. In fact, he’s had to break free from the prison of his senses and grieve that loss. The source of his inspiration derives from what the ancient Greeks referred to as Agape, self-less love, which came to be translated as “charity” in the first English versions of the Bible. It comes from the power Shakespeare has to address his fellow man, demonstrating through the work of his own creative process, his working through of the paradoxes of love, loss, mortality, and the pursuit of happiness—it is the selfless act, which Shakespeare puts before his audience.

Shakespeare should not be approached as some towering immortal God who stands above us all. Quite the opposite: he is our fellow mortal. The essence of Shakespeare’s work, the hypothesis which underlies the higher hypothesis, is the acceptance of his mortality. It is the realization of those paradoxes that define the mortal life, our passions, and our desires to possess, whether it be people, things, or love; it is the world that opens up as we come to the ultimate realization of having to let go of all these things—that is Shakespeare, and that is life.

If we wish to know him, we need only undertake this same journey.

This essay was first published here in April 2020.

The Imaginative Conservative applies the principle of appreciation to the discussion of culture and politics—we approach dialogue with magnanimity rather than with mere civility. Will you help us remain a refreshing oasis in the increasingly contentious arena of modern discourse? Please consider donating now.


[1] Daniel R. Leach, “John Keats’ “Great Odes” & the Sublime,” The Imaginative Conservative, June 12, 2019.

[2] Hildegard Hammerschmidt-Hummel, Das Geheimnis um Shakespeares ‘Dark Lady’: Dokumentation einer Enthüllung, Wiss. Buchges., 1999.

The featured image is a portrait of William Shakespeare (1610) by John Taylor (1585-1651) and is in the public domain, courtesy of Wikimedia Commons.

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