The 10 Most Devastating Insults of All Time

By:
The French call it "l'esprit d'escalier," or "staircase ghost." To the rest of us, it is known simply as the comeback, that divine and tender coincidence of all the universe's comedic forces at the perfect moment. A truly good comeback can instantly turn tables, elevate the terminally zinged to the status of champion, and reduce the zinger to a stuttering fool. Sadly, many of us will go our entire lives without scoring a decent comeback, doomed to pause awkwardly and mutter some pathetic variation of "your face ” for the rest of our miserable lives. For us, it must be enough simply to marvel at the comebacks of the better equipped, and possibly memorize them for later personal use. After all, you never know when you're going to have to take that bitch Lady Astor down a peg.

John Wilkes vs. John Montagu (AKA The Earl of Sandwich)

The Players: Most sources credit this exchange to John Wilkes and John Montagu, the Earl of Sandwich, although occasionally it’s also credited to British Prime Ministers Benjamin Disraeli and William Gladstone. I’m going to assume Sandwich said it, because it’s less satisfying to make fun of a guy who is considered the precursor of the modern politician than a guy who invented putting stuff in bread. Setting the Scene: When not revolutionizing the consumption of sliced meats and cheeses, Montagu was known for his incompetence, cruelty, lechery, and Satan-worshipping. The Earl was a member of The Hellfire Club, a “satanic” group dedicated to amoralistic hedonism, which totally explains all the sandwiches. There’s not a lot more seductively evil than a hot pastrami on rye. He was also responsible for commanding the British navy at the time of the American Revolution, and his incompetence at doing so is considered by historians to have been a large deciding factor in the war, so much so that when he died a popular proposed epitaph was “Seldom has any man held so many offices and accomplished so little.” Posthumous zing! Basically, the Earl of Sandwich was exactly like that Jack in the Box commercial made him out to be.
John Wilkes, another politician and member of The Hellfire Club, apparently pointed this out to him at some point, because the two were mortal enemies for most of their lives. Wilkes even famously Punk’d him by releasing a baboon dressed in a cape and horns at a meeting of THC while Sandwich was “invoking Satan.” It’s said to be this incident that inspired Sandwich to clutch his fear-soiled robes about himself and declare-- The Zing: “Sir, I do not know whether you will die on the gallows or of the pox.” To which Wilkes replied-- The Comeback: “That will depend, my lord, on whether I embrace your principles or your mistress.” Then the baboon clawed Sandwich’s face off while the real Satan appeared and congratulated Wilkes on the burn.
What We Would Have Said: “Well I do know. I will die on the gallows…for murdering thee--in the face!”

Related: The Insane Life of the Man Who Killed John Wilkes Booth

Winston Churchill vs. Lady Astor

The Players: Winston Churchill, one of Britain’s best-loved Prime Ministers, helped lead the nation to victory in World War II by sitting on his fat ass, smoking cigars, and delivering more quotable lines than an entire staff of Simpsons writers. Churchill was such a powerful force in English politics that his death ensured work for ugly British actors for at least the next millennia. During his time in Parliament, he often had the occasion to square off against the conservative Lady Astor, first female member of Parliament and renowned wit. Whether Astor’s penchant for attacking Churchill was due to his being a heavy drinker, occasionally sexist, or simply a worthy sparring partner, their scuffles proved that if there’s anything politicians do well, it’s talk some serious shit.
Setting the Scene: I should actually say “scenes.” Astor, who eventually became a Christian Scientist, didn’t much cotton to Churchill’s habit of smoking cigars by the case while double-fisting whiskey sours. Churchill may have started the rivalry when he compared Astor’s election to Parliament to be “like being intruded upon in the bathroom.” To which Astor replied “you’re not handsome enough to have such fears.” Reportedly Churchill then choked on a lungful of cigar smoke, eyed her through the haze, and muttered “it’s on now.” And on it was, with such exchanges as: Churchill: “What disguise would you recommend I wear to your costume ball?” Astor: “Why don’t you come sober, Prime Minister?” Astor: “If you were my husband, I’d poison your tea.” Churchill: “Madam, if you were my wife, I’d drink it.” But perhaps the best-loved Astor/Churchill battle is the following, made doubly impressive by the fact that, by the admission of both parties, Churchill was visibly drunk at the time--
The Zing: “Mr. Churchill, you are drunk!” The Comeback: "Yes, and you, Madam, are ugly but tomorrow I shall be sober and you will still be ugly." What We Would Have Said: “I won World War II, Ass-turd, so shut it. You know, Nazis? Hitler? Your face .”

Related: Gangstas vs. Rednecks: Weirdly Similar Subcultures

Dorothy Parker vs. Clare Boothe Luce

The Players: Dorothy Parker and Clare Boothe Luce are the type of women destined to make this list. Both were renowned for their incisive wit, both were prolific and award-winning writers, and both loved a good old-fashioned cat fight. Parker was one of the founding members of the Algonquin Roundtable, a group of writers, editors, and intellectuals who met for lunch every day to say quotable things and laugh urbanely about how much smarter than the general public they all were. Luce, aside from being a playwright, served as U.S. Ambassador to Italy and a Congresswoman, thereby posthumously zinging the hell out of Lady Astor.
Setting the Scene: By the time these two fulfilled their comedic destinies, they had a lot to be pissy about. Parker had become a left-wing activist, picketing for Sacco and Vanzetti, penning the disillusioned Oscar-winner A Star Is Born, and promptly getting blacklisted by the McCarthy machine. Meanwhile, Luce had converted to Roman Catholicism and become more conservative than ever, as well as one of the leading voices against the “growing threat of Communism.” Basically, they did everything they could to become exact opposites of one another, short of Parker getting a sex change. Thus, when they arrived simultaneously at the front door of the Waldorf-Astoria hotel to attend a party, both had to get a dig in. Luce began the proceedings by holding the door for Parker and intoning--
The Zing: “Age before beauty.” Parker then ended the proceedings by stepping through the door and shooting back-- The Comeback: “Pearls before swine.” Luce’s Bible then burst into flames, burned its way out of her purse onto the ground, and flipped open to that particular verse while the Pope, who had been arguing with the guy at the check-in counter, started to high five Parker repeatedly. What We Would Have Said: “More like beauty before age! Which is why I’m going first, because I’m the most beautiful, and also the oldest. So yes, age and beauty both first, together. Fuck you and your stupid face.”

Related: 6 Famous Quotes You See On Facebook (That Are Crazy Fake)

Buddha vs. Random Asshole

The Players: Not a lot of religious figureheads are known for their sharp wit. Jesus kind of painted himself into a corner with the whole “turn the other cheek” thing, and Jehovah’s idea of a comeback was killing your entire town in a rain of brimstone and blood. Not exactly Friar’s Club Roast material. Meanwhile, Mohammed’s pathetic attempts at insult are the stuff of legend, and while Joseph Smith once said something about Vishnu winning an “arms race,” the reference was lost on most in attendance. Yes, in the religious world, Siddhartha “The Buddha” Guatama is the undisputed king of zing. Raised in a palace and educated as a prince, he had the broad knowledge base required for improvisational mockery. And, as a proponent of balance in all things, he’s one of the few religious figures who can justify the use of a withering comeback. After all, what better way to balance out an insult than an insult of equal force in the opposing direction? This concept encompasses all the teachings of Buddhism (there’s some Newtonian physics mixed in there too).
Setting the Scene: Buddha was meditating beneath a tree, as he is wont to do, and presumably wondering why he found it so difficult to shed those few extra pounds of belly fat (hint: try standing up some time). Naturally, this made The Buddha cranky, so when some random asshole started hurling petty insults at him, he decided to get all Socratic on his ass a full century before Socrates was even born. The lesson goes something like this-- The Zing: Asshole: “Buddha, you are one fat piece of work. Wow. I hope you eat some bad pork and die.” Buddha: “If a man offered a gift to another but the gift was declined, to whom would the gift belong?" Asshole: “To the one who offered it…but I really don’t see where you’re going with—“
The Comeback: Buddha: “Then I decline to accept your abuse and request that you keep it for yourself.” The asshole was then spontaneously reincarnated as the lowest form of life, a list-based comedy writer. What We Would Have Said: “You’ll be sorry when I’m Enlightened! Then you’ll pay…then you’ll all pay, right through your stupid faces.”

Related: Gangstas vs. Rednecks: Weirdly Similar Subcultures

Winston Churchill vs. George Bernard Shaw

The Players: Churchill you may remember from several minutes ago. At this point in our story, he’s still the British Prime Minister, still drinks and smokes like a fish’s chimney, and still seems to spout off horrendous burns like some kind of reverse fireman. This time, the target of his fire hose is George Bernard Shaw, Irish playwright, author of
Pygmalion, and Socialist extraordinaire. Shaw spent most of his life crusading for the working class, even going so far as to donate the monetary portion of his Nobel Prize in literature to the effort to translate Swedish works of literature into English. This also qualified him for the Nobel Prize in Most Obscure Donation, the financial proceeds of which he used to build a gold statue of himself.
Setting the Scene: When Shaw’s play Major Barbara went up (or by some accounts Pygmalion), he decided to invite Winston Churchill to the opening via personal telegram. Shaw and Churchill had what could be termed a “friendly rivalry” going on, insofar as both had at one point publicly called the other vastly overrated. But since Nobel Laureates are “above” expressing rivalry by punching each other mercilessly in the shoulder, Shaw’s telegram read--
The Zing: “Have reserved two tickets for opening night. Come and bring a friend—if you have one.” Churchill wired back-- The Comeback: “Impossible to come to first night. Will come to second night—if you have one.” Churchill then chuckled at his own telegram, rolled over in bed, and helped Lady Astor sneak out the fire escape. What We Would Have Said: “Request another ticket, as I am bringing two friends--my balls. Will introduce them to your face.”

Related: 4 Noble (Yet Goofy) Attempts To Make The English Language Less Of A Trainwreck

Calvin Coolidge vs. Dorothy Parker

The Players: Calvin Coolidge isn’t known for a lot. He’s one of those Presidents you tend to shuffle into the Pearce/Taylor/Hayes/Garfield category, and even Garfield inspired a fat cartoon cat. Any cartoon character inspired by Coolidge would likely be “cold, distant, silent and detached,” as papers of the day described him. And while I personally would find a cold and detached cartoon cat to be an awesome concept for a comic strip, no brave artist has as yet stepped up to the plate. Until then, we’ll have to satisfy ourselves with this anecdote, which will probably have a more lasting impact on the nation than anything else “Silent Cal” did while in office.
Setting the Scene: Coolidge earned his reputation for silence at a string of lavish dinner parties thrown by New York and Washington’s high society. When asked why he attended so many of these parties, despite seeming to be a general downer at them, he shrugged and said, “Got to eat somewhere.” So you get an idea of what a great guy he was. At a particular party, Dorothy Parker—the pearls/swine lady from before—decided that devouring the soul of Clare Boothe Luce wasn’t enough; she wanted the President. Turning to him, she said-- The Zing: “Mr. Coolidge, I've made a bet against a fellow who said it was impossible to get more than two words out of you.”
The Comeback: “You lose.” Coolidge continued staring into his soup, spoon poised, waited for a proper amount of awkward silence to pass, then slurped continuously for upwards of twenty seconds. Although Parker still got Coolidge in the end, famously responding to the news of his death by asking “How can they tell?” Posthumous zing number two! What We Would Have Said: “Your face.”

Related: 6 Overlooked Details That Turn Beloved Characters Into Jerks

Winston Churchill vs. Francis Crick

The Players: Yes, the estate of Winston Churchill is sponsoring a large portion of this article. In case you’ve forgotten, he’s the UK PM with Hitchcock’s physique and Castro’s capacity for oral tobacco intake. Francis Crick, along with his loyal manservant Watson, sleuthed the basic helical structure of DNA and single-handedly foiled the evil Professor Moriarty. Setting the Scene: When Cambridge put in a chapel in the early 60’s, Crick, who at that time was keeping busy nailing the hell out of his bio students and driving around in a Beemer with the vanity plate “ACGT,” became morally outraged and resigned his post. As it is a British the custom to grind salt into the wounds of fellow celebrities by mail, Winston Churchill wasted no time in sending Crick a letter “consoling” him for the loss he suffered due to his stubborn ideals.
The Zing: Churchill’s letter urged Crick to take back his old job and try not to mind about the church. After all, he argued, “its mere existence should be of no consequence, as no one will be forced into it against his will.” The Comeback: “Dear Mr. Churchill. Enclosed are ten guineas towards the construction of a brothel at Cambridge. Its mere existence should be of no consequence, as no one will be required to enter it against his will.” Crick then performed his patented victory move, “The Helix,” though as the insult had been delivered through the mail, much of the effect was lost. What We Would Have Said:
“Here’s ten guineas, ugly. Go fix your face.”

Related: 5 Great Scientists Who Believed Wildly Unscientific Things

Oscar Wilde vs. Lewis Morris

The Players: Oscar Wilde, author of The Importance of Being Earnest and The Picture of Dorian Gray, was a renowned Irish playwright and wit who wore fur coats in public, had catty feuds with other poets, and just went around generally acting so gay that he was ultimately put on trial and imprisoned for his homosexuality. His works and legacy are still going strong, despite tremendous efforts to silence his “indecency” in his own time, although his is still occasionally mistaken for actor Gene Wilder, probably because he’s as close to Willy Wonka as any living human’s ever been. Lewis Morris was another poet and friend of Oscar’s who wasn’t nearly as gay and has therefore rightly been forgotten.
Setting the Scene: It seems Mr. Morris was a bit of a Kanye, as one evening found him bitching to his friend Wilde about his narrowly missing being appointed Poet Laureate of the United Kingdom. In fact, as it’s probably his association with Wilde that cost him the appointment, we should imagine the complaints to be suitably passive-aggressive. At the time, Wilde was probably organizing his legal defense, which ended up being so eloquent it was later adapted into a popular play.
The Zing: More of a whine, actually. But Morris reputedly complained-- “There's a conspiracy against me, a conspiracy of silence; but what can one do? What should I do?" Wilde shuffled in his satin robe, roused from a deep Opium dream, and answered--
The Comeback: “Join it.” Then came his signature fluting laugh, and the chorus of naked boys burst into scattered applause. Then Calvin Coolidge appeared from beyond the grave to give him a Presidential thumbs up. What We Would Have Said: “Here’s a poem, you emo prick: Ace of Base, shut your face.”

Related: Sorry, Governor Zack Morris Is Probably A Republican

Neils Bohr vs. Albert Einstein

The Players: Albert Einstein, a Nazi defector, is best known for the series of posters he appeared on with his tongue sticking out. He also invented radiation, daily exposure to which tragically caused him to always have “static electricity hair.” This obvious physical defect led to his name becoming synonymous with idiocy or buffoonery (i.e., “great job irradiating my turtles, Einstein; they’ve transformed into man-sized ninja monsters”). Neils Bohr was a Nobel Laureate physicist with the Manhattan Project who provided powerful insights into atomic structure and early quantum mechanics. His mother was from a wealthy political family, his father had a molecular function named after him (the “Bohr shift”), and his brother was an Olympian. He is considered to be one of the fathers of modern physics, and was considered “adequate” by his parents.
Setting the Scene: When quantum mechanics first introduced the idea of probability wave functions, a lot of physicists were like “what? I don’t even know what that is.” Then when it was explained that this basically implied a certain amount of indefinable and inscrutable uncertainty on the atomic level, most were still confused, but some started to get pissed off. One of these some was Einstein, a religious man, who proclaimed quantum theory bunk on the grounds that--
The Zing: “God does not play dice.” Bohr, being better acquainted with God’s gambling habits, offered the following advice-- The Comeback: “Don’t tell God what to do with his dice.” Two large dice then crashed down from the heavens, killing Einstein and proving God’s existence once and for all. The people rejoiced.
What We Would Have Said: “Yeah he does, ass! That’s exactly what I’m saying!”

Related: 7 Quotes By Famous Geniuses (That Everyone Gets Wrong)

Keith Moon vs. Jimmy Page

The Players: Keith Moon, of The Who, is one of the greatest drummers and rock stars to ever grace a stage. His unique style of drumming like a goddamned madman and insisting that the drums be treated as a lead instrument paved the way for 32-piece, revolving drum sets everywhere. Further, his habit of utterly trashing hotel rooms, throwing TV sets out of windows, and blowing up toilets got him personally banned from no less than three major hotel chains and basically started the trend. He was a tortured, bizarre little man who hit his women, forced enough drugs through his system to mildly discomfort Keith Richards, and made some of the best noises in the history of rock. I’d tell you who Jimmy Page is, but that kind of gives away the comeback, so I’ll act like you’ve lived under a rock for forty years and have no idea.
Setting the Scene: One night, Robert Plant, John Entwhistle, Page and Moon were partying together at Moon’s house. We can safely presume both were high out of their minds, and at this point in the night had wearied of driving cars into pools full of groupies. Plant took the edge off by telling Moon all about his concept for a new rock band of tight-jeaned, open-shirted, long-haired men singing ten minute songs in falsetto about goblins raiding Middle Earth. Shaking off the effects of the horse sedatives he’d just taken rectally, Moon pulled himself out of the haze long enough to analogize-- The Zing: “That idea will go over like a lead zeppelin.”
The Comeback: The entire Led Zeppelin discography, not to mention the fact that more people associate Jimmy Page with the hard-rockin’ lifestyle than even know who the hell Keith Moon was. What We Would Have Said: “Is that girl’s pubic hair on fire? Seriously, Keith, what the hell is going on man? I’m really worried about you. Also, you’ve got some food on your face.”
When not writing for Cracked, Michael finds it increasingly difficult not to read a Churchill biography as head writer and co-founder of Those Aren't Muskets!

Related: That Story About Robbie Williams And Jimmy Page Is Likely BS

Join the Cracked Movie Club

Get your weekly round-up of the latest movie and TV coverage from Cracked and be entered for our digital projector giveaway!

Recommended For Your Pleasure

Forgot Password?