Shakespeare's sassiest moments

Miriam Sallon 12 November 2021

Drama and tragedy are synonymous with Shakespeare and so too is sass and downright rudeness—here are some of the best examples

It's well-known that Shakespeare contributed an obscene amount to the English vernacular, creating countless idioms now so commonplace we don’t even think to credit them. “Too much of a good thing” (As You Like It), for example, or “vanishing into thin air” (Othello). Or even something so banal as “all of a sudden” (The Taming of the Shrew).

Indeed, many of his contributions have been so wholly swallowed by the English language, you might think him without any edges at all, his works merely a stuffy reference book sandwiching pedestrian phrases with completely implacable speeches by dead kings.

But don’t let him mislead you! Shakespeare wasn’t all reverence and twee poetry. He also knew how to take someone down with a single line, to “make a laughing stock” of them (The Merry Wives of Windsor). But beware, this article is not for the “faint-hearted” (Henry VI. Sorry, that’s the last time we’ll do that!)

So, here’s a list of Shakespeare’s most cutting insults, and sassiest one-liners:

“Villain, I have done thy mother”—Titus Andronicus 4.2

Perhaps the first noted “your mum” joke in history, delivered in a slightly more literal context than is now considered polite.

“Item, I give unto my wife my second-best bed”

Arguably his shadiest moment, found in his will and testament. Scholars now claim this wasn’t such an unusual bequeathment, the first-best bed generally being saved for guests where the second-best was the matrimonial bed. But it’s also generally agreed that most people would mention their spouses more than just the once in their testament. And knowing how capable Shakespeare is of a double-meaning, we’re taking this personally, on poor Anne’s behalf.

“I must tell you friendly in your ear, sell when you can, you are not for all markets”—As You Like It 3.5

Delivered by a woman disguised as a man trying to insult a woman who grows more and more attracted to him/her the ruder he/she is. Both of whom would have been played by men. Classic Shakespeare. It’s the added “friendly” that makes this so particularly cutting.

“Would thou wert clean enough to spit upon”—Timon of Athens 4.3

“I’ll beat thee but I would infect my hands”—Timon of Athens 4.3

“I do wish thou were a dog, that I might love thee something”—Timon of Athens 4.4

All delivered in a single act, Shakespeare really packs in the punches here. Classic one-liner insults that would still wound today. Please don’t try these at home!

“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”—Sonnet 130

One of his best-known sonnets, this is really the original “My Funny Valentine”, and the ultimate backhanded compliment. Noting her ordinariness and ugliness over and again, he waits until his mistress's ego is at its very lowest before remarking that, indeed his “love is rare”. Pff.

“Thou whoreson zed, thou unnecessary letter!”—King Lear, 2.2.65

Brilliant in its seeming innocuousness. The letter “z” was in even less usage in Shakespeare’s day, having been excluded from the Latin alphabet in the fourth century BC and only reintroduced much later. So, it hung idly at the end of the alphabet, having little to no use, much like Oswald according to the Earl of Kent in King Lear.

“More of your conversation would infect my brain... I will be bold to take my leave of you.”—Coriolanus 2.1

This comes at the end of a serious slating from Menenius who berates Brutus and Sicinius for not caring about the common people of Rome. While they point out that he’s hardly a perfect civil servant, Menenius gets the last line in and then exits. Mic drop.

“I do desire we may be better strangers.”—As You Like It 3.2

Who doesn’t know someone they wish they could say this to? So polite, so calm, just a simple, “I wish I didn’t know you”. How do you argue with that, besides slinking away, mortified? Except that it’s said by Orlando in response to Jaque’s “Let’s meet as little as we can.” So let’s say, no-one wins this one.

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