The 16 Sickest Burns of All Time

History is teeming with pithy insults, snide asides, and mic-drop moments so sick you can’t help but respect their inventors—whether you feel sorry for their targets or not. From a story of Truman Capote responding to indecent exposure with a withering comeback to the time when Virginia Woolf compared James Joyce’s Ulysses to pimple-popping, here’s a list of legendary burns from history, adapted from an episode of The List Show on YouTube.

1. Roger Ebert’s Review of Mad Dog Time

Roger Ebert skewered dozens of awful movies during his decades as a film critic, but his review for Larry Bishop’s 1996 crime comedy Mad Dog Time, with a cast that included Jeff Goldblum and Ellen Barkin, just might be his most creative takedown. He wrote that “Mad Dog Time is the first movie I have seen that does not improve on the sight of a blank screen viewed for the same length of time. … Watching [it] is like waiting for the bus in a city where you’re not sure they have a bus line.”

It gets better. And by better I obviously mean worse. Ebert closed his critique with a suggestion for the film:  “Mad Dog Time should be cut into free ukulele picks for the poor.”

 2. Truman Capote’s Diss of a Rude Bar Patron

One night at a packed bar in Key West, Florida, a woman approached Truman Capote and asked him to autograph her napkin. He was happy to oblige, but the request irritated the woman’s inebriated husband. 

As Capote later recalled, “he staggered over to the table, and after unzipping his trousers and hauling out his equipment, said: ‘Since you’re autographing things, why don’t you autograph this?’”

A hush fell over the area as other bar patrons waited to see how Capote would respond. He didn’t disappoint. “I don’t know if I can autograph it,” he said. “But perhaps I can initial it.” Yet another reason to keep your pants on in public.

 3. Vinegar Valentines

Behind the posh facade of Victorian society were certain impolite customs—like vinegar Valentines. These cards featured catty rhymes that insulted anyone from an unwanted admirer to the worst singer on your street. Here’s part of one that does just that, titled “You are a nerve-destroyer.”

“When a pig’s getting slaughtered, the noise that it makes
Is sweeter by far than your trills and your shakes;
And the howling of cats in the backyard at night,
Compared with your singing’s a dream of delight.
Your squalls and your bawls are such torture to hear, 
A man almost wishes he had not an ear.”

The tradition lasted well into the 20th century and crossed the pond to the U.S., too. Here’s the poem from one Vinegar Valentine that shows a slick-haired suitor about to smooch a donkey:

“Hey, lover boy, the place for you
Is home upon the shelf,
’Cause the only one who’d kiss you
Is ... A jackass like yourself!”

Imagine finding that in your locker on Valentine’s Day.

 4. Elizabeth Taylor’s Dig at Her Male Co-Stars

As far as we know, Elizabeth Taylor never sent a caustic holiday card to any of her human male co-stars. But she did diss most of them in a 1981 interview for The Times of London, saying, “I reckon some of my best leading men have been dogs and horses.”

Granted, Taylor was a lifelong animal lover. She owned a number of dogs during her life, and she even handpicked the horse she rode in the 1944 film National Velvet. But since animals are generally considered to be the worst possible co-stars—along with kids—Taylor’s comment seems pretty shady.

 5. Virginia Woolf’s Takes on Ulysses

Virginia Woolf was more than shady when criticizing James Joyce’s novel Ulysses. In a 1922 diary entry, she expressed that the first few chapters had “amused” and “charmed” her. For the rest of the first 200 pages, she was “puzzled, bored, irritated, & disillusioned as by a queasy undergraduate scratching his pimples.”

But the pimple parallel ventured beyond her private diary. She used it again when sharing her thoughts on that first chunk of Ulysses with fellow writer Lytton Strachey. The third through sixth chapters, she wrote, were “merely the scratching of pimples on the body of the bootboy at Claridges.​​” Woolf, added (charitably?), “Of course genius may blaze out on page 652 but I have my doubts.”

 6. Gore Vidal and Norman Mailer’s Talk Show Zingers

Woolf was far from the only 20th-century writer to critique their contemporaries. Gore Vidal and Norman Mailer did it right in each other’s faces—on national television. In 1971, the two appeared on The Dick Cavett Show some time after Vidal had published a piece in The New York Review of Books in which he’d accused Mailer of misogyny and likened him to Charles Manson.

The segment (above) was more of a verbal boxing match than an interview. At one point, Mailer said, “It’s hard when you have a lot in your head to write something that’s true. Gore has never encountered this problem.”

Vidal’s response? “What did you say? I wasn’t listening.”

Mailer had actually headbutted his opponent backstage before the show—and it wasn’t the last time the feud turned physical. At a party years later, Mailer threw his drink in Vidal’s face and also punched him. Vidal kept his cool, delivering some version of this mic-drop moment: “Norman, once again words have failed you.”

 7. H.G. Wells and Henry James’s Literary Barbs

H.G. Wells and Henry James were frenemies, too. They started out as friends, but both began to feel like the other’s work fell short of expectations. In a 1912 letter to Mary Ward, James described Wells as having “so much talent with so little art.” 

He didn’t stop there. In the same letter, he said of Wells: “I really think him more interesting by his faults than he will probably ever manage to be in any other way.”

Wells, meanwhile, shared his thoughts on James’s work in his 1915 satirical novel Boon, writing, “It is like a church lit but without a congregation to distract you, with every light and line focused on the high altar. And on the altar, very reverently placed, intensely there, is a dead kitten, an egg-shell, a bit of string … ”

He also didn’t stop there: “It is a magnificent but painful hippopotamus resolved at any cost, even at the cost of its dignity, upon picking up a pea which has got into a corner of its den.” This round goes to Wells. 

 8. William Faulkner’s Ernest Hemingway Diss (And Hemingway’s Hit Back)

In 1947, a creative writing student at the University of Mississippi asked William Faulkner to rank the leading writers of the era, himself included. Faulkner awarded himself second place, behind Thomas Wolfe. Ernest Hemingway came in fourth—not too shabby, until you hear what Faulkner had to say about him:

“He has no courage, has never crawled out on a limb. He has never been known to use a word that might cause the reader to check with a dictionary to see if it is properly used.”

According to A.E. Hotchner’s 1966 memoir Papa Hemingway, the slight eventually made its way to Papa himself. He shook it off with a string of very powerful small words.

“Poor Faulkner. Does he really think big emotions come from big words?” Too bad the two never got to face off in Scrabble.

 9. William Faulkner’s Mark Twain Barb

Faulkner had been dissing other authors since the ‘20s. In one piece he called Mark Twain “a hack writer who would not have been considered fourth rate in Europe, who tricked out a few of the old proven ‘sure fire’ literary skeletons with sufficient local color to intrigue the superficial and the lazy.” Not only an affront to Mark Twain, but also to anyone who liked his work. But before you feel too sorry for Samuel Clemens, you should know that Faulkner did later recognize his genius. 

 10. Mark Twain’s Anti-Austen Stance

Twain dished out some even harsher insults during his heyday. In an 1898 letter to fellow writer Joseph Twichell, Twain complained that he couldn’t bring himself to critique Jane Austen’s work. Not because he loved it—but because he loathed it so much that he couldn’t “conceal my frenzy from the reader.”

And then he wrote this creatively horrifying barb: “Every time I read Pride and Prejudice I want to dig her up and beat her over the skull with her own shin-bone.”

 11. Theodore Roosevelt Versus The World

While the Huck Finn author was busy harboring resentment toward Austen, Theodore Roosevelt was penning poison about, well, everyone else. Usually in private correspondence, but still.

He called author Henry James a “little emasculated mass of inanity.” Woodrow Wilson’s secretary of state, William Jennings Bryan, was labeled “a professional yodeler, a human trombone.” And Postmaster General John Wanamaker was “an ill-constitutioned creature, oily, but with bristles sticking up through the oil.”

But nobody got the Bull Moose treatment quite as bad as William Howard Taft. TR basically hand-picked Taft to take over the Oval Office after him—and Taft succeeded in getting elected. Unfortunately, TR’s one-time protégé failed to live up to expectations, and so became the inspiration for some of TR’s most biting burns. He called him a “puzzlewit,” a “fathead,” and a “flubdub with a streak of the second-rate and the common in him.”

Teddy was also fond of measuring people’s intelligence in units of what he called “guinea pig power”—a creative spin on using horsepower to talk about engine output.

According to TR, British ambassador Sir Mortimer Durand had “a brain of about eight-guinea-pig-power.” It wasn’t a compliment, but compared to Roosevelt’s assessment of Taft—“brains less than a guinea pig”—it might as well have been.

 12. H.L. Mencken’s FDR Diss

Journalists have also done their fair share of roasting politicians over the years. In 1936, H.L. Mencken wrote an article in The American Mercury lambasting Franklin Delano Roosevelt for, in Mencken’s view, being a shameless opportunist: “If he became convinced tomorrow that coming out for cannibalism would get him the votes he so sorely needs, he would begin fattening a missionary in the White House backyard come Wednesday.”

The piece was so inflammatory that someone at a White House press conference asked Roosevelt himself for a response. He said he hadn’t read it. But according to Mencken’s biographer Marion Elizabeth Rodgers, Mencken didn’t believe that.

13. George Orwell’s Critique of Stanley Baldwin

Meanwhile, across the pond, Conservative politician Stanley Baldwin was serving his third and final stint as the UK’s prime minister. In George Orwell’s opinion, which he shared in a 1941 essay titled “The Lion and the Unicorn: Socialism and the English Genius,” Baldwin royally botched the country’s foreign policy. As Orwell wrote, “one could not even dignify him with the name of stuffed shirt. He was simply a hole in the air.” 

 14. Dorothy Parker’s Calvin Coolidge Diss

Critic Dorothy Parker had similar feelings toward Calvin Coolidge, though hers were more about personality than policy. The 30th president could apparently be conversational and witty behind closed doors. But in public he often seemed taciturn, earning him the nickname “Silent Cal.”

In January 1933, Parker was reportedly at a theater performance when she found out that Coolidge had just died. Her response? “How can they tell?” Some sources cite Parker’s remark as “How do they know?”—which was also reportedly how playwright Wilson Mizner responded to the news of Coolidge’s death. The possibility that two people uttered this same sick burn makes it twice as rough—and twice as fortunate that Coolidge, at least, never heard it.

15. Dorothy Parker’s Girl O’ Mine Review

The creators of the Broadway musical Girl O’ Mine, on the other hand, probably did find out what Parker had to say about their project. Her not-so-glowing review was printed in the April 1918 issue of Vanity Fair. Parker wrote, “Girl O’ Mine is one of those shows at which you can get a lot of knitting done. I turned a complete heel without once having my attention distracted by anything that happened on the stage. … By all means go to Girl O’ Mine if you want a couple of hours’ undisturbed rest. If you don’t knit, bring a book.” 

 16. Mariah Carey’s “I Don’t Know Her”

But as Mariah Carey taught us, saying basically nothing can sting worse than even the most inspired insults. While talking to German media outlet Taff in the early 2000s (above), Carey gushed about Beyoncé. “I love Beyoncé,” she said, calling her “fabulous” and “a great writer, a great singer,” among other things. When asked for her opinion on Jennifer Lopez, the Queen of Christmas delivered the most scathing four-word retort in pop star history: “I don’t know her.”

The moment has gotten the meme treatment ever since, and Carey has leaned into it as part of her legacy. Upon seeing a fan sporting an “I don’t know her” shirt at a concert, she snuck the words “I still don’t know her” into the song “Love Takes Time.”

The diva also sort of hinted at how the beef began in her 2020 memoir The Meaning of Mariah Carey. When Carey divorced Sony executive Tommy Mottola and left the label in the late 1990s, she was already working on the soundtrack for her 2001 movie Glitter. The first single, “Loverboy,” was supposed to include a sample from Yellow Magic Orchestra’s song “Firecracker.”

According to Carey, Mottola and Sony sabotaged that plan to get back at Carey for her departure. “After hearing my new song,” she wrote, “using the same sample I used, Sony rushed to make a single for another female entertainer on their label (whom I don’t know).”

That single was “I’m Real” by Jennifer Lopez. According to Sony producer Cory Rooney, who worked on “I’m Real,” it was just a coincidence that his team also chose “Firecracker.” Coincidence or not, Carey ended up replacing the sample and harboring some less-than-fuzzy feelings toward J.Lo. 

For what it’s worth, Carey has clarified that she wasn’t saying she didn’t know who J.Lo was—just that she didn’t know her well enough to share a positive opinion. In 2018, she told Pitchfork that she “was trying to say something nice or say nothing at all.”