Winston Churchill’s Wicked Sense of Humor: Eight Clever Remarks from the Old Chap

In lieu of the recent commemoration of Winston Churchill’s fiftieth death anniversary, let us look at another side of this great man’s personality – his wit and sharp tongue – through these eight clever comebacks, jokes and retorts that came out of his mouth.

WWII British Prime Minister Winston Churchill is greatly remembered as the greatest prime minister Britain has ever had with his indefatigable spirit which pushed the country through the tumultuous years of the Second World War. The great war leader, though, is also known for another thing — his sharp tongue. His ability to make up clever one-liners may be one of the factors why his legend is kept alive trough these long five decades after his death.

Here are the witty, funny and clever sayings from the celebrated politician himself — Sir Winston Churchill.

On Poison and Coffee

This anecdote about the prime minister’s word showdown with viscountess and known to be the first female member of the Parliament, Nancy Astor, is, perhaps, the most well-known in this “clever lines” list.

It was common fact in those times that these two figures have a mutual dislike for each other and couldn’t be in each other’s company without a battle of words ensuing.

The most familiar duel of words between Churchill and Astor happened when the latter visited Blenheim and it so happened that the WWII leader was also there. Nancy Astor was said to have commented “If I were your wife I would poison your coffee…”

To which Sir Winston Churchill promptly replied with “And if I were your husband, I would drink it”.

Firing Insult with Insult

Exchanging insults may not be the best form of entertainment but this one gets its place in this “clever lines” list because it’s amusing.

The British Prime Minister during WWII had always admitted he and alcohol had a “relationship” and this one ensued from his drinking spirits.

It was said that while Churchill was leaving the House of Commons sometime in 1946, MP Bessie Braddock hit him with an insult saying “Winston, you are drunk, and what’s more you are disgustingly drunk.”

Churchill fired back at her with an insult, too, saying “Bessie, my dear, you are ugly, and what’s more, you are disgustingly ugly. But tomorrow I shall be sober and you will still be disgustingly ugly.”

It seemed that the WWII prime minister borrowed lines from W. C. Fields in the 1934 film It’s a Gift. In this picture, when told he was drunk, Fields’ character quipped “Yeah, and you’re crazy. But I’ll be sober tomorrow and you’ll be crazy the rest of your life.”

Toilet Humor

Toilet humor, though low-class, can be hilarious and though this one’s not the funniest in this said joke genre, surprisingly, the WWII prime minister had one clever toilet one-liner of his own.

When he was disturbed from his “thinking time in the throne” by a call from Lord Privy Seal, Churchill easily responded with “Tell him I can only deal with one s*** at a time”.

On Meeting the Maker Face to Face

When asked by a reporter if he was prepared to meet his maker, the respected leader responded with an answer which bordered on the serious and the amusingly witty:

“I am ready to meet my maker. Whether my maker is prepared for the great ordeal of meeting me is another matter.”

Alcohol for Better Health?

Winston Churchill and alcohol had a rather complicated relationship. many historians reject the notion that the WWII prime minister was an alcohol “abuser” and apparently, he also was not dependent on alcohol or he wouldn’t have won his 1936 bet with Rothermere — the bet was whether he could or could not abstain from drinking hard spirits within a year.

One of Winston Churchill famous clever quips about his friendship with alcohol makes it to this list of the prime minister’s witty lines. During a reception in Washington DC while WWII was running, the British politician made this famous retort:

“All I can say is that I have taken more out of alcohol than alcohol has taken out of me.”

Chamberlain and Crocodile Feeding

The WWII prime minister was very vocal about his feelings of former British Prime Minister Neville Chamberlain’s appeasement policy with Adolf Hitler — he was against it. Nothing expressed those feelings well compared to this line – which was funny if taken into imagination – which he likened Chamberlain to a crocodile feeder.

“An appeaser is one who feeds a crocodile, hoping it will eat him last.”


Churchill’s wit were more than barbs and retorts to his detractors. The WWII leader also used his sharp tongue to deliver praises to those whom he deemed worthy of them. UK Prime Minister from 1945 to 1951, Clement Attlee, was one of these men.

When asked what he thought about the man, Sir Churchill said this famous clever line:

“A modest man, who has much to be modest about.”

Birthday Doldrums

Chamberlain, Baldwin and Churchill
Chamberlain, Baldwin and Churchill

Former Prime Minister Stanley Baldwin and WWII British Prime Minister Winston Churchill had, what we call, a love and hate relationship. Churchill had worked in Baldwin’s cabinet and the former had even asked opinions from the latter but in the end, their comradeship suffered a fallout and historians point out political and decision differences the culprits.

So, when Churchill was asked why he declined to give Baldwin a birthday card on his eightieth birthday, here was his clever quip:

“I wish Stanley Baldwin no ill, but it would have been much better if he had never lived.”

Heziel Pitogo

Heziel Pitogo is one of the authors writing for WAR HISTORY ONLINE