7 Hilarious Zingers From History’s Biggest Smartasses

We all know a smartass. You might be a smartass yourself. Since the beginning of human history, the smartass has been there, defying authority with sarcastic remarks, and making sure nothing ever gets too serious. The smartass knows how to be witty when others just get angry. We’ve gathered up 7 of the finest moments in smartass history from history’s most sarcastic assholes.

1. Diogenes


Diogenes was an ancient Greek philosopher well-known for his smartass behavior. He lived in a wine cask and had no possessions.

Smartass moment:
It was said that when Alexander the Great arrived at the city he was interested in meeting Diogenes. He saw him resting in the sunlight, introduced himself as Alexander the Great, and asked the philosopher if there was anything he could do for him. Diogenes replied, “Yes. Get out of my sunlight.”



2. Winston Churchill

Winston Churchill

Winston Churchill was Prime Minister of the U.K. and led the country through WWII. And he was also one of history’s biggest smartasses.

Smartass moment:
Churchill was once accused by a woman of being ‘disgustingly drunk’ His response? “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.”

What a burn.

3. Sparta


The Spartans were Greek’s most notorious smartasses. There are many fantastic quotes from Spartans, and their brief, witty comebacks are the reason for the word “laconic” (the area around Sparta was Laconia).

Smartass moment:
After invading parts of Greece and conquering other key cities, Philip II communicated a threatening message to the Spartans: “If I invade Laconia you will be destroyed, never to rise again.” The Spartans replied with a single word: “If”.


4. Gandhi


Gandhi led India’s independence movement from the British while practicing non-violent protest forms that influenced the entire world. Buuuut he was also kind of a smartass.

Smartass moment:
A reporter once asked Gandhi “What do you think of Western civilization?” His response: “I think it would be a good idea”.


5. Abraham Lincoln

Abraham Lincoln

The American president may be remembered more for the Gettysburg Address than his personality, but he was a classic smartass.

Smartass moment:
During the Lincoln-Douglas debates, Douglas called Lincoln two-faced. Lincoln replied, “Honestly, if I were two-faced, would I be showing you this one?”

Fair enough, Abe.

6. Arthur Wellesley

Arthur Wellesley

Arthur Wellesley was the 1st Duke of Wellington, a soldier, and a statesman. Oh, and a smartass.

Smartass moment:
A woman apologized for the rude behavior of some French officers who had turned their backs on him when he entered the room. His reply? “I have seen their backs before, Madam”.


7. John Wilkes
John Wilkes

John Wilkes was an English radical politician. And a witty one at that.

Smartass moment:
The Earl of Sandwich said to Wilkes: “Sir, I do not know whether you will die on the gallows or of the pox.” And Wilkes replied “That will depend, my lord, on whether I embrace your principles or your mistress.”


That’s it! Now go out there and be the best smartasses you can be, History Hustlers.

Be the first to comment on "7 Hilarious Zingers From History’s Biggest Smartasses"

Leave a comment

Your email address will not be published.