12 Jokes About Famous, Historical Leaders

Throughout history, people have made jokes about their leaders. The following set of jokes are focused on historical figures so don’t expect that you’ll find something on those currently in power.

And remember, “Never get into fights with ugly people because they have nothing to lose.”

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Leadership Jokes on Historical Figures

Meeting The  Pope

A man walked into Joe’s Barber Shop for his regular haircut. As he snips away, Joe asks “What’s up?”

The man proceeds to explain he’s taking a vacation to Rome.

“ROME?!” Joe says, “Why would you want to go there? It’s a crowded dirty city full of Italians! You’d be crazy to go to Rome! So how ya getting there?”

“We’re taking TWA,” the man replies.

“TWA?!” yells Joe. “They’re a terrible airline. So where are you staying in Rome?”

The man says “We’ll be at the downtown International Marriot.”

“That DUMP?!” says Joe. “That’s the worst hotel in the city! The rooms are small, the service is surly and slow and they’re overpriced! So whatcha doing when you get there?”

The man says “We’re going to go see the Vatican and hope to see the Pope.” “HA! That’s rich!” laughs Joe. “You and a million other people trying to see him. He’ll look the size of an ant. Boy, good luck on THIS trip. You’re going to need it!”

A month later, the man comes in for his regular haircut. Joe says, “Well, how did that trip to Rome turn out? Betcha TWA gave you the worst flight of your life!”

“No, quite the opposite” explained the man. “Not only were we on time in one of their brand new planes, but it was full and they bumped us up to first class. The food and wine were wonderful, and I had an attendant who waited on me hand and foot!”

“Hmmm,” Joe says, “Well, I bet the hotel was just like I described.”

“No, quite the opposite! They’d just finished a $25 million remodeling. It’s the finest hotel in Rome, now. They were overbooked, so they apologized and gave us the Presidential suite for no extra charge!”

“Well,” Joe mumbles, “I KNOW you didn’t get to see the Pope!”

“Actually, we were quite lucky. As we toured the Vatican, a Swiss guard tapped me on the shoulder and explained the Pope likes to personally meet some of the visitors, and if I’d be so kind as to step into this private room and wait, the Pope would personally greet me. Sure enough, after 5 minutes the Pope walked through the door and shook my hand. I knelt as he spoke a few words to me.”

Impressed, Joe asks, “Tell me, please! What’d he say?”

“Oh, not much really. Just “Where’d you get that awful haircut?”

Mototov The Follower

There was a time in the nineteen forties when Vyacheslav Molotov was Soviet foreign minister. He was a shrewd man and a hard bargainer but worked for Joseph Stalin, who was The Boss.He was once overheard talking to Stalin by trans-Atlantic telephone during the course of some very intricate negotiations with the West. He said, “Yes, Comrade Stalin,” in quiet tones, then again, “Yes, Comrade Stalin, and then, after a considerable wait, “Certainly, Comrade Stalin. Suddenly he was galvanized into emotion. “No, Comrade Stalin,” he barked, “No. That’s, no. Definitely, no. A thousand times, no!”

After a while, he quieted and it was “Yes, Comrade Stalin,” again. The reporter who overheard this was probably never so excited in his life. Clearly, Molotov was daring to oppose the dictator on at least one point, and it would surely be important to the West to know what that point might be.

The reporter approached Molotov and said as calmly as possible, Secretary Molotov, I could not help but hear you say at one point, “No, Comrade Stalin.”

Molotov turned his cold eyes on the reporter and said, “What of it?”

“May I ask,” said the reporter, cautiously, “What the subject under discussion was at that time?”

“You may,” said Molotov. “Comrade Stalin asked me if there was anything which he had said with which I disagreed.”

The Greats Don’t Need Hair Cuts

A young boy had just gotten his driving permit. He asked his father, who was a minister, if they could discuss the use of the car. His father took him to his study and said to him, “I’ll make a deal with you. You bring your grades up, study your Bible a little and get your hair cut and we’ll talk about it.” After about a month the boy came back and again asked his father if they could discuss use of the car. They again went to the father’s study where his father said, “Son, I’ve been real proud of you. You have brought your grades up, you’ve studied your Bible diligently, but you didn’t get your hair cut!”

The young man waited a moment and replied, “You know Dad, I’ve been thinking about that. You know, Samson had long hair, Moses had long hair, Noah had long hair, and even Jesus had long hair….” To which his father replied, “Yes, and they walked every where they went!”

Churchill and Twain

Winston Churchill and Mark Twain met for the first time in 1900, when Churchill was just coming into prominence as a young statesman. The meeting took place at a dinner in London. During the dinner, they decided to step outside for a smoke.

An observer, Sir William Harcourt, speculated that since both men tended to dominate conversations, the one who got the floor first would keep it. He told others at his table that since Twain was older and more experienced, Churchill’s voice would get the first rest it had had in a long time.

When the two return, Harcourt asked the young Churchill if he had enjoyed talking to Twain. Churchill replied with an enthusiastic “Yes.” Harcourt then asked Twain if he had a good chat with Churchill. Twain paused, then said, “I had a good smoke.”

Calvin Coolidge—A Man of Few Words

As a government function in the nineteen-twenties, a young lady approaching President Coolidge, said gushingly, “Oh, Mr. President, I have made a wager with a friend of mine that I could persuade you to say more than two words to me. Could you?” And Coolidge, without expression, said, “You lose.”

Calvin Coolidge, famous for his silence, had been to church. When he returned, he said nothing about the service. His wife prompted him. “What was the sermon about?” she asked. “Sin,” Cal answered. “Well, what did the preacher say about sin?” she asked impatiently. “He was against it,” Cal told her.

Bill Clinton: On Running a Country

So if you are having a problem with people you are not alone. President Clinton once said running a country is a lot like running a cemetery; you’ve got a lot of people under you and nobody’s listening.— in a speech at Galesburg, III.

Jack Kennedy—Buying An Election

In March 15, 1958 and young politician in his 40’s by the name of Jack Kennedy went to the spotlight. Kennedy’s opening line became part of his legend. Previously, his father John had been lampooned in the press as trying to use his family’s money and influence to buy the election. Reaching into his pocket he, pulled out a telegram he said he had just received from his dad. It said, “Dear Jack, Don’t buy a single vote more than is necessary–I’ll be damned if I’m going to pay for a landslide.”

How President’s Relax

George Bush, Boris Yetsin and Fidel Castro had a summet meeting on a cruise ship. Toward the end of the day, they adjourned and went onto the ship’s deck. Boris then pulled open a fifth of vodka, took a couple mouthfuls and threw it overboard. When the other two looked at him, he said, “In Russia, we got many fifths of vodka.” Then Fidel lit a cigar, took a couple of puffs and it overboard. When the other two looked at him, he said, “In Cuba, we got many of cigars.” George was wondering what he was going to do when he had an idea. He grabbed the first person he saw and threw him overboard. When the other two looked at him he replied, “In America, we have many illegal aliens.”

George Washington and the Cherry Tree

When Harry was a young boy in Louisiana, he was always getting into trouble. One morning while waiting for the school bus, he pushed the outhouse into the bayou and went off for school as if nothing had happened. When he returned, his father was waiting for him. He said, “Son, did you push the outhouse into the bayou?” “Yes, father,” said Harry, “like George Washington, I cannot tell a lie.” Harry’s father took off his belt and said, “All right, son, bend over. I’m going to have to whip you.” Harry tried to explain that Mr. Washington didn’t spank George when he admitted chopping down the cherry tree. “Yes, son,” said Harry’s father, “but George’s father wasn’t in the tree.”

Bill Gates in Heaven

God called three individuals to announce his intentions toward the human race. At the meeting were George Bush, Vladimir Putin, and Bill Gates. God announced that he was putting an end to the human race in 30 days and that each was to tell there followers.

Vladimir Putin goes back to his followers and tells them, “I have some bad news and some terrible news. The bad news is that our communist ideology was wrong. The terrible news is God is putting an end to everything in thirty days.”

George Bush goes back to his followers and says, “I have some bad news and good news.” The good news is our religion is correct, there is a God. The bad news is that God is putting an end to everything in 30 days.”

Bill Gates goes back to his followers and says, “I have good news and better news. The good news is that I am one of the three most important humans on the planet according to God. The better news is we won’t have to ship the next version of Windows.

Theodore Roosvelt—On Being a Republican

While delivering a campaign speech one day Theodore Roosevelt was interrupted by a heckler: “I’m a Democrat!” the man shouted.
” May I ask the gentleman,” Roosevelt replied, quieting the crowd, “why he is a Democrat?”
” My grandfather was a Democrat, my father was a Democrat and I am a Democrat.”
” My friend,” Roosevelt interjected, moving in for the kill, “suppose your grandfather had been a jackass and your father was a jackass. What would you then be?”
Alas, Roosevelt was thwarted by the quick-witted heckler, who promptly replied: “A Republican!”

Theodore Roosevelt—On Exercise

President Theodore Roosevelt’s enthusiasm for exercise posed a continual challenge to Washington’s diplomatic corps. On one White House visit, Jusserand was invited – after two sets of tennis – to go jogging. A workout with the medicine ball followed. Then, his guest’s enthusiasm apparently flagging, Roosevelt asked, “What would you like to do now?”
” If it’s all the same to you,” the exhausted Frenchman sighed, “lie down and die

Harry Truman—On Becoming a President

On April 12th, 1945, Harry Truman was summoned to the White House. Ushered into Eleanor Roosevelt’s sitting room, the vice president was gently informed that President Roosevelt had died.
” Is there anything I can do for you?” Truman asked after a moment’s reflection. “Is there anything we can do for you?” Eleanor replied. “You’re the one in trouble now!”

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