10 Hilarious Historical Moments of Insults and Trash Talking

History tends to remember the best qualities of historical figures. For example, most people today have no idea that Benjamin Franklin had a sharp wit and an incredible ability to tactfully insult people. Larry Bird is best remembered for his seemingly superhuman ability to shoot the basketball, but his tongue was just as sharp as his shooting form.

The art of cleverly delivering an insult is as old as humanity itself. Trash talking, one form of this art, is the act of taunting opponents with words that would be considered inappropriate in polite society. But the truly great insult is much more than that. It’s an art form where insults are mixed with humor to soften the blow or sharpened with wit to cut even deeper. From the sports arena to the halls of power, a perfectly timed put-down can win the battle before it even begins.

Let’s take a few minutes to enjoy 10 of the funniest and most fearsome insulters of all time.

Related: The 10 Most Useless Inventions in Human History

10 Benjamin Franklin’s Witty Battles with Britain

Benjamin Franklin was America’s most famous diplomat, and his greatest weapon was his unequaled wit. While living in Europe, he grew tired of the stuffy, pretentious academic societies, including Britain’s, which he felt focused on impractical and pointless questions. Instead of arguing with them directly, he decided to mock them so cleverly that it became a legendary intellectual prank, and a subtle jab at the British-influenced scientific establishment.

In 1781, in response to a call for papers from the Royal Academy of Brussels, Franklin penned a satirical essay later nicknamed “Fart Proudly.” In it, he proposed that the great scientific minds of the day stop their useless debates and focus on a practical problem plaguing mankind: the foul odor of human flatulence. He suggested research into foods and a drug that could make farts smell like perfume. The essay was one of the best historical examples of brilliant satire, using a vulgar topic to expose the absurdity of the so-called intellectual elite, thumbing his nose at the establishment from across the Atlantic.^[1]

9 Larry Bird’s Battle-Sharpened Tongue

Larry Bird is universally recognized as one of the greatest basketball players of all time. Still, his physical gifts were not what made him terrifying. He wasn’t the fastest or most athletic, but he would mentally destroy his opponents with a constant barrage of trash talk. For example, before the 1988 NBA Three-Point Contest, he walked into a locker room filled with the league’s best shooters, looked them all in the eye, and asked a simple question: “So, who’s coming in second?”

This wasn’t an isolated incident. Bird’s cruel-but-hilarious trash talk often had tactical precision. He would famously tell his defender exactly how he was going to score on him. Then he would flawlessly execute the play exactly as he had predicted. Decades after his retirement, his opponents still talk about how his words got inside their heads, with a combination of respect and awe.

It’s incredibly difficult to master the art of trash-talking. Larry Bird taught us that it takes a combination of factors: an incredible amount of self-confidence, being able to back up your words with action, and an extremely calm, almost bored, delivery.^[2]

8 “Nature Boy” Ric Flair: The Charismatic Wrestler with the Non-Stop Mouth

It’s extremely rare for a 44-second monologue of trash talk to get four million views on YouTube, but “Nature Boy” Ric Flair is the textbook master of the wrestling promo. His genius lay in insulting you by simply describing his own extravagant lifestyle. In the unforgettable 1980s-era video, Flair screams into the microphone about his Rolex watches, his custom-made shoes, and his alligator-skin belts—all aimed at intimidating his opponent.

Ric Flair was one of the most charismatic wrestlers of all time, and his career lasted for more than 50 years. He endured so long by developing a character so over-the-top that it was impossible to ignore him. He laid the foundation that later wrestlers such as Stone Cold Steve Austin and The Rock built upon.

This particular promo is one of Flair’s most popular of all time. In addition to being watched over 4 million times, the video currently has almost 2,000 comments. Its cultural impact was such that in 2015, NFL player Sergio Brown and his fellow Indianapolis Colts teammates replicated Flair’s performance line-for-line in their locker room.^[3]

7 Groucho Marx: The Master of the One-Line Insult

Groucho Marx was the true master of the one-line insult, and one wonders if such a cutting comedian could survive in today’s more sensitive and politically correct times. However, his delivery was so sharp and funny that his one-line antics are now legendary.

On his game show You Bet Your Life, no one who stepped on stage was safe from his sardonic wit. He treated his contestants with a loving disrespect that became his trademark, telling one woman with a perfectly straight face, “You’re one of the most beautiful women I’ve ever seen, and that’s not saying much for you.” He would pry into their lives with absurd questions, asking another, “Is it true you’re getting a divorce as soon as your husband recovers his eyesight?”

The foundation of Marx’s brilliance was that he insulted people directly to their faces, but his undeniable charm and the ever-present twinkle in his eye made it impossible to be truly offended. He wasn’t mean-spirited; he was just ridiculously quick-witted. Like Robin Williams much later, with Groucho Marx, you had to laugh because his jokes were the product of sheer comedic genius.^[4]

6 How Abraham Lincoln Skewered His Opponents with Words

Before his presidency, Abraham Lincoln was an Illinois lawyer celebrated for his wit and homespun humor. The immense strain of the Civil War might have shattered a less resilient man, but Lincoln found relief in jokes and anecdotes. Through tales and probing questions, he could make his legal opponents look foolish. He was a master of using his unassuming demeanor, disarming rivals before verbally eviscerating them in the courtroom or on the debate stage.

On one occasion, after a political adversary delivered a fiery oration, Lincoln waited for him to finish. He then rose and dismissed the entire speech by comparing its impact to the fleeting fizzle from an opened bottle of soda water. Lincoln had a way of insulting a person in an unassuming and almost gentle way. He could win a battle of wits with a single metaphor, slicing an opponent to pieces with his dry humor.

His wit was never sharper than when he turned it on himself. During a debate, his rival, Stephen Douglas, accused him of being two-faced. Instead of getting angry, Lincoln calmly turned to the crowd with a sad smile. He told them that if he really had another, better face, he certainly wouldn’t be wearing this one. The crowd erupted in laughter, Douglas’s insult was neutralized, and Lincoln once again proved that the best defense was a humble and hilarious punchline.^[5]

5 Conor McGregor: The Trash Talker Who Missed His Calling as a Stand-Up Comedian

Conor McGregor might just be the greatest trash talker in UFC history. More than just a fighter, he was a master of psychological warfare who understood that the battle began long before the first bell rang. His trash talk was infused with an incredible amount of natural humor; it was often much funnier than it was vicious. The UFC press conference became his personal stage, a comedic roast where no opponent was safe from his lightning-fast wit and devastating one-liners.

McGregor’s verbal attacks were meticulously crafted to get inside his opponents’ heads. He would mock their clothes, their fighting style, and even their manhood with a huge, infectious grin. He famously derided one opponent’s “pea-shaped head” and weak chin, and dismissed fighting others as “easy money.” He also pioneered a unique form of insult by boasting about his own immense wealth, framing a fight against him not as a challenge but as a financial lottery ticket for his rivals—a “red panty night” for their family, as he famously put it.

He understood that modern sports were as much about entertainment as they were about competition. His quick comebacks and hilarious, often absurd observations made him a global superstar, with compilations of his best moments garnering millions of views. McGregor proved that in the modern era, a fighter’s sharp tongue and ability to sell a fight could be just as powerful as a sharp left hook. Never one for humility, he perfectly captured his ethos at one of his most memorable press conferences by mockingly apologizing to “absolutely nobody.”^[6]

4 Mark Twain: America’s Great Wit and Social Critic

Mark Twain was a master of insulting people so cleverly that his insults often went over their heads. His targets were not specific rivals but grand concepts like politics, religion, and societal hypocrisy. He once demonstrated his contempt for government by suggesting that the labels “idiot” and “Congressman” were essentially interchangeable.

His chosen weapon was satire, and he wielded it with clinical precision. Through his novels, he exposed the absurdities of his time by showing society its own unflattering, but true, reflection. He offered observations that served as timeless advice and also as subtle insults, famously advising that it was far better to remain silent and be thought a fool than to open your mouth and prove it beyond all doubt.

Twain’s wit was sharpened by a difficult life filled with financial struggle and personal tragedy. This led his later work to become darker and more critical of humanity, as he evolved from a simple humorist into a biting social critic. His work has never lost its power because his insults were aimed at the foolishness of all mankind. For this reason, his words remain a masterclass in using humor to speak truth to power.^[7]

3 Oscar Wilde: The Man Who Made the Insult an Art Form

Oscar Wilde treated every conversation like a performance and every sentence like a work of art. His supreme self-confidence was his trademark. Arriving in America for a lecture tour, he famously told a customs official that he had nothing to declare but his own genius.

His insults were delivered so beautifully that the target often felt complimented. They were subtle traps, wrapped in elegant language. He once called a disastrous theatrical performance a complete success, adding that it was the audience, not the play, that had been a failure. He could summarize a man’s entire unlikable character by observing that he had no enemies but was intensely disliked by his friends. The damage was done before the victim even understood the attack.

In the high-society circles of London, Wilde’s wit was a weapon for social domination. He could dismantle a rival’s reputation with a smiling comment from across a dinner table. His verbal attacks were so clever and well-crafted that to take offense was to admit you simply weren’t smart enough to be in on the joke. He left his opponents intellectually checkmated, cementing his status as a master of the artful takedown.^[8]

2 Winston Churchill: The Prime Minister of Put-Downs

Winston Churchill’s wit was forged in the fires of political survival and World Wars I and II. His insults were brutally efficient weapons intended for immediate destruction. Leading a nation on the brink of collapse, Churchill treated Parliament like a battlefield where words had the power of artillery. He understood that a debate was a fight, and a perfectly aimed put-down could demolish an opponent’s argument, rally his allies, and project an image of unshakable strength when Britain needed it most.

His most legendary comebacks were exercises in total annihilation, leaving no room for a counterattack. The most famous example was his exchange with Lady Astor, a frequent political rival. When she cornered him with the hypothetical, “Winston, if you were my husband, I’d poison your tea,” she intended to publicly shame him. Churchill’s instant reply, “Nancy, if I were your husband, I’d drink it,” was a masterstroke of verbal warfare.

Churchill consistently turned his own perceived weaknesses into strengths. Accused by a Member of Parliament of being disgracefully drunk, he calmly admitted it. “My dear, you are ugly,” he replied, “but tomorrow I shall be sober.” He mastered taking valid criticisms and using them as a foundation for a far more permanent and vicious personal attack. Whether facing a direct assault or simply dismissing a rival, like Clement Attlee, whom he called “a sheep in sheep’s clothing,” his method was the same: end the fight quickly, strategically, and decisively. His wit was the ultimate tool of a political brawler, a man who completely mastered the art of winning.^[9]

1 Muhammad Ali: The Greatest Trash Talker of All Time

Muhammad Ali is, was, and always will be the undisputed king of the insult. He transformed talking trash into poetry, prophecy, and performance art. He mentally broke his opponents long before they ever stepped into the ring, using his rhymes, predictions, and unshakable confidence as psychological weapons. He was the godfather of modern trash talk, insulting his opponents’ skill, their looks, their intelligence, and even their humanity with a creative flair that the world had never seen before.

He told the heavily muscled boxer Sonny Liston that he was far too ugly to be the world champion, and Ali used lyrical, rhyming boasts to predict the exact round in which Liston would be defeated. Ali’s verbal attacks were a spectacle in and of themselves, filled with hyperbolic metaphors about his grace, skill, agility, and power. He famously claimed to have wrestled alligators and handcuffed lightning, painting a grandiose picture of a man so mean that he made medicine sick.

Ali may be the most creative and influential trash talker that the world has ever known. He understood that the fight began at the press conference, not at the opening bell. He invented the art of the athletic boast, and he perfected it, laying a firm foundation for future masters of the art of talking trash: Michael Jordan, Larry Bird, Conor McGregor, and others.^[10]