George Bernard Shaw: Have reserved two tickets for opening night, Bring a friend, if you have one. Churchill: Impossible to come to first night. Will come to second night, if you have one.
Lady Astor: Winston, if you were my husband, I’d put poison in your coffee. Churchill: Nancy, if you were my wife I’d drink it.
A Member of Parliament: Mr. Churchill, must you fall asleep while I’m speaking. Churchill: No, it’s purely voluntary.
Bessie Bradock: Winston, you are drunk! Churchill: That’s right, Bessie. But tomorrow morning I’lll be sober. And you will still be ugly.
There is also an exchange about haggling with a woman over what he could pay to sleep with her, but it has also been attributed to several other people, so I have not included it.
The Bradock insult isn’t as clever - it’s something I’m sure he’d thought of before. But the rest were all quick retorts in response to receiving an insult. A great insulting comeback is always better than a great insult.
Roger Ebert must have been well-read about Churchill. All the Ebert obits yesterday and today (e.g., this one) have been quoting a very similar thing he said, after having dissed Vincent Gallo’s film Brown Bunny.
Not an insult, and probably apocryphal, but…
At one point the Prime Minister was introduced at a function by a member of the rival party.
The member ended his introduction by marking the wall behind him just above his head, and stating: “If all the liquor Mr. Churchill has consumed over the years were poured into this room, it would reach this high.”
Winston walked up. Looked at the mark, then the ceiling, and said: “So little time. So much to do.”
The young Churchill wore a daringly fashionable mustache. A society matron (not Astor, AFAIK) took exception at a (liberal) political comment and snapped, “Young man, I care for neither your politics nor your mustache!” “Madame,” he replied, “you are unlikely to come in contact with either.”
Family Guy on time traveling and discovering Churchill’s “legendary wit”:
Lady Astor: Oh Winston, drunk again I see?
Winston Churchill: yeah? Well you’re a cunt.
(or on broadcast)
Winston Churchill: yeah? Well you’re a fat bitch.
I’ve also always liked the one where Churchill walks into the boys room, occupied at the time by his Labour Party predecessor Clement Attlee, tending to business at one end of a long row of urinals. WC takes his place at the far end. “What’s the matter?” asks Attlee. “Feeling stand offish today, Winston?” “No,” replies WC. “Frightened. You want to nationalise every big thing you see.”