Churchill is widely known as one of the greatest orators of all-time, and not just because his speeches were tight as hell: he also knew how to throw shade like none other.
When he bested Bessie:
One night in 1946, Churchill got particularly shithoused in the House of Commons, as British politicians are wont to do. As he was staggering his way out to head home, he literally stumbled into Bessie Braddock, a Labour MP from Liverpool.
"Winston," she bellowed, "you are drunk, and what's more, you are disgustingly drunk."
Churchill then took a good look over Bessie—a woman of ample proportions, if you know what I mean—and retorts, "And might I say, Mrs. Braddock, you are ugly, and what's more disgustingly ugly. But tomorrow, I shall be sober, and you will still be disgustingly ugly."
When he rekt Clement:
One of Churchill's most famous one-liners is his description of Clement Attlee, “a modest man with much to be modest about,” though that wasn’t actually the most devastating own Churchill unleashed upon the prime minister who unseated him after WWII. That one took place in the bathroom in the House of Commons.
After yet another parliamentary debate (classic), Churchill found himself in need of a little relief, and set out toward the Bathroom of Commons. Once inside, he noticed Attlee at-loo and chose to use a urinal at the farthest end instead of alongside the pinko politician.
Of course, Attlee took note of this and commented, "Winston, I know we're political opponents, but we don't have to carry our differences into the gentlemen's lavatory."
"Clement," Churchill replied, "the trouble with you Socialists is that whenever you see anything in robust and sturdy condition you want the government to regulate it."
When he described basically anything:
Speaking of famous one liners, some of these just need no introduction nor context, and certainly no umbrella—there’s plenty of shade here.
- On Russia: "In Russia, a man is called a reactionary if he objects to having his property stolen and his wife and children murdered."
- On John Foster Dulles, US Secretary of State from 1953-59: "Dull, duller, Dulles."
- On Charles de Gaulle, leader of the Free French during WWII and eventually president of France from 1959-70: "He looks like a female llama who has just been surprised in her bath."
When he shamed Chamberlain:
In September 1938, most of the major European powers took a trip out to Munich to see what Hitler had to say, which was like definitely not a bad idea. One of the attendees was the then-prime minister of the UK, Neville Chamberlain.
The UK had traditionally been on friendly terms with the Czechs, but this dude didn’t care so much about that as he did about getting Hitler to quit bothering everybody—so he thought. The result was the Munich Agreement, which permitted Germany to annex parts of Czechoslovakia.
When Chamberlain returned to London feeling pretty good about himself, Churchill precipitously said: “He was given the choice between war and dishonor. He chose dishonor and he will have war anyway.”
More like ChamberSLAIN, am I right?!
When he shut down (yet another) Socialist:
Churchill, being a man who preferred to do the talking himself—if there was going to be talking at all—didn't always enjoy long ass House of Commons sessions. During one particularly dull discussion launched by—of course—a Socialist, Churchill opted instead to get a little shut-eye.
Once the speaker noticed the slumbering Minister, he asked "Must the right honorable gentleman fall asleep when I am speaking?"
Like a Snorlax to a Poké Flute, Churchill suddenly awoke and replied, "No, it is purely voluntary."
When he literally shit-talked:
If it’s not already clear, Churchill was a notorious shit-talker when it came to Socialists. Arguably his best analogy with regard to that, uh... movement... came following the defeat of the Conservatives after the war, when Churchill was also suffering through a nasty bout of pneumonia.
One day while he was still bedridden, his nurse noticed that, after she removed his bedpan, he started quietly chuckling. She goes, "Mr. Churchill, I don't see anything funny about taking out a bedpan."
Churchill replied, "It's not you. I'm congratulating myself. It's the first time a movement I've backed has been carried out since the Socialist government came in."
When he tore up Lady Astor:
Despite their similar, rich as fuck upbringings, Churchill and Nancy Astor never really got along. He dragged her many times over the course of his life, but probably the most injurious of them all happened in the 1930s.
This was during a period where Lady Astor was part of a crew in the House of Commons who thought Hitler had some good points, actually. Churchill was never a big Hitler fan, but one night he was obligated to attend a dinner at Cliveden, the Astor mansion.
The lady herself chose to serve post-dinner coffee, and as she was pouring Churchill’s, she said, “Winston, if I were your wife, I’d put poison in your coffee.”
“Nancy,” Churchill said as he switched from coffee to tea, “if I were your husband, I’d drink it.”
When he dragged a whole dinner:
Say what you will about Churchill, you gotta admit that he'd be (and was) one hell of a party guest. But that didn't necessarily mean he enjoyed all of them.
He gave this particularly savage review after a friend asked him how a dinner party he'd attended in London the previous night had been: "Well, it would have been splendid... if the wine had been as cold as the soup, the beef as rare as the service, the brandy as old as the fish, and the maid as willing as the Duchess."
When he laid into his in-law:
Churchill's oldest daughter, Sarah, married a man named Vic Oliver, a music hall comedian. From the very beginning, he and his father-in-law had a tempestuous relationship, probably because what the hell is a "music hall comedian"? This forced association was only exacerbated by Oliver's bizarre habit of referring to Churchill as "Popsy."
One night during dinner at Chartwell, the Churchill family estate, Oliver asked his father-in-law: "Popsy, who, in your opinion, was the greatest statesman you have ever known?"
"Benito Mussolini," the actual greatest statesman surprisingly replied.
Obviously taken aback, Oliver responds, "What? Why is that, Popsy?"
"Mussolini is the only statesman who had the requisite courage to have his own son-in-law executed,” Churchill then says/slays.
When he came for himself:
To be a truly shady individual, one must be willing to occasionally trash oneself.
By the age of 78, Churchill had rightfully begun to give even less of a fuck than he previously had. While he was waiting to give a speech, an aide passed him a note which read, "Prime Minister—your fly is unbuttoned."
Promptly addressing the issue at hand, Churchill wrote back, "Never fear. Dead birds do not drop out of nests."