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20 of the best insurance jokes

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Even though insurance is rarely a laughing matter, that doesn’t mean that we can’t sometimes laugh at the silliness of some aspects of this business, or just laugh to melt the stress away. And, after all, the best free medicine is laughter.

Tasteful jokes can also be used as ice-breakers when meeting new people or doing a presentation. Joking tends to relax everyone and, if done right, can actually make people relate to you. Just make sure that you practice your repertoire before your presentation; you don’t want to seem too cheesy, or worse, a creepy jokester.

We searched high and low on the internet to find some of the best insurance jokes out there. Do you know some jokes that weren’t included in our list? Add them in the comments section below.


1. Statue

An insurance agent went to a museum and he accidentally hit a statue.

Museum Administrator: “That’s a 500-year-old statue you’ve broken!”

Insurance agent: “Thank God! I thought it was a new one.”


2. Happy boss

A happy insurance boss says to his employees, “You worked very hard this year. As a reward, I’ll give everyone a check for $5,000. If you work with the same zeal next year, I’ll sign those checks.”


3. The underwriter & his wife

Underwriter’s wife: “You always carry my photo in your handbag to the office. Why?”  

Underwriter: “When there is a problem, no matter how impossible, I look at your picture and the problem disappears.”  

Underwriter’s wife: “You see how miraculous and powerful I am for you?”  

Underwriter: “Yes, I see your picture and say to myself, ‘What other problem can there be greater than this one?’” 

mature and expensive


4. Woman, man & insurance

These two jokes are compliments of students in CE seminars:

Question: Do you know what a woman and insurance have in common?

Answer: They are both expensive, difficult to understand and what you get is not guaranteed.

Question: Do you know the difference between a man and a whole life policy?

Answer: A whole life policy eventually matures.


5. Confucius says…

“Needing insurance is like needing a parachute. If it isn’t there the first time, chances are you won’t be needing it again.”



6. It had to be an actuary

Three men are sentenced to die by guillotine. The first man steps up, places his head in the hole, the executioner releases the knife, and, miraculously, the knife stops inches above the man’s neck. The king says, “Under the laws of our country, if the guillotine fails to do its job, you are declared free.”

So, the first man gets up, relieved, and the second man takes his place. Again, the guillotine knife stops inches away from the man’s neck. The king says again, “Under the laws of our country, if the guillotine fails to do its job, you are declared free.”

So, the second man gets up, free. The third man, who is an actuary, puts his head in the guillotine hole, looks up, and says, “I think I see what the problem is…” 

go figure

7. When God created actuaries

What did God say when he created actuaries? He scratched his head and said, “Go figure!”

They took it literally.


8. A doctor, an engineer & an actuary

A doctor, an engineer and an actuary were arguing about which was the oldest profession. The doctor stated that God created Eve from Adam’s rib, which was of course a surgical procedure. The engineer argued that, earlier, God had created order from chaos, which was an engineering feat. “But,” asked the actuary, “Who created the chaos?”


9. An actuary and a Mafia don 

Question: What’s the difference between an actuary and a Mafia don?

Answer: The actuary can tell you how many people will die this year. The Mafia don can tell you the names of all of them.


10. Applying for life insurance

The applicant for life insurance was finding it difficult to fill out the application. The salesman asked what the trouble was, and the man said that he couldn’t answer the question about the cause of death of his father.

The salesman wanted to know why. After some embarrassment, the client explained that his father had been hanged.

The salesman pondered for a moment. “Just write: ‘Father was taking part in a public function when the platform gave way,’” the salesman said.


11. Seven insurance agents

“You ought to feel highly honored,” said the businessman to the life insurance agent. “So far today, I have had my secretary turn away seven insurance agents.” “Yes, I know,” replied the agent, “I’m all of them.”


12. Genie grants a wish

An insurance sales rep, an administration clerk and their manager are walking to lunch when they find an antique oil lamp. They rub it and a genie comes out in a puff of smoke. The genie says, “I usually only grant three wishes, so I’ll give each of you just one.” “Me first! Me first!” says the admin clerk. “I want to be in the Bahamas, driving a speedboat, without a care in the world.”

Poof! She’s gone.

In astonishment, “Me next! Me next!” says the sales rep. “I want to be in Hawaii, relaxing on the beach with my personal masseuse, an endless supply of piña coladas and the love of my life.”

Poof! He’s gone.

“Ok, you’re up,” the genie says to the manager. The manager says, “I want those two back in the office after lunch.”

Moral of story: Always let your boss have the first say. 


13. How did your grandpa die?

A life insurance agent was completing an application and got to the part on health history. He asked his client how his grandfather died. This was his client’s startling answer: “I want to die in my sleep like my grandfather…Not screaming and yelling like the passengers in his car.”


14. Don’t be jittery

A retired insurance agent, now in his mid-70′s and about to receive anesthesia, is on the operating table awaiting surgery. He insisted that his son, a renowned surgeon, should perform the operation.

The old man signaled to speak to his son.

“Yes, Dad, what is it?” asked the son. “Don’t be jittery son, perform your best, and never forget that if it fails, if something should happen to me, your mother will live with you and your wife the rest of her days.”

grim reaper

15. Three weeks

Suffering from a bad case of the flu, the outraged patient bellowed, “Three weeks? The doctor can’t see me for three weeks? I could well be dead by then!” Calmly the voice at the other end of the line replied, “If so, would you please have your wife call to cancel the appointment?”


16. The lawyers

My dinner party was headed for disaster. One man, an insurance salesman, was monopolizing the conversation with a lengthy account of recent litigation involving himself. Since two other guests were lawyers, I was becoming increasingly uneasy.

“In the end,” the salesman concluded, “you know who got all the money?” I cringed when he shouted, “The lawyers!”

There was embarrassing silence at the table. My heart was pounding until the wife of one lawyer said, “Oh, I do love a story with a happy ending!” 


17. Three wishes

An agent walking along the beach found a bottle. When he rubbed it, lo and behold, a genie appeared. “I will grant you three wishes,” announced the genie. “But since Satan still hates me, for every wish you make, your rival gets the wish as well — only double.”

The salesman thought about this for a while. “For my first wish, I would like $10 million,” he said. Instantly, the genie gave him a Swiss bank account number and assured the man that $10 million had been deposited in it. “But your rival has just received $20 million” the genie said.

“I’ve always wanted a Ferrari,” the salesman said. Instantly, a Ferrari appeared. “But your rival has just received two Ferraris,” the genie said.

“And what is your last wish?” “Well,” said the salesman, “I’ve always wanted to donate a kidney for a transplant.”


18. Be nice to your kids

Be nice to your kids. They will choose your nursing home.


19. Lose a husband

“Do you know the present value of your husband’s policy?” the life insurance agent asked his client.

“What do you mean?” countered the woman. 

“If you should lose your husband, what would you get?” asked the agent.

The woman thought for a minute, then brightened up and said, “Probably a poodle.”

train tunnel

20. Train tunnel

An underwriter, an insurance agent, an old lady and a beautiful blonde find themselves together on a train. The train passes through a tunnel and, in the darkness, a loud slap is heard. When the train came out of the tunnel and into the light, they see that the insurance agent has a red five-finger mark on his cheek.

The blonde thinks: “The insurance agent must have tried to grope me in the dark and mistakenly groped the old lady, so she slapped him.”

The old lady thinks: “That guy must have groped the blonde in the dark and she slapped him.”

The insurance agent thinks: “The underwriter must have groped the blonde in the dark and she mistakenly slapped me instead of him.”

The underwriter thinks: “I can’t wait for the next tunnel, so I can slap that insurance agent again!”


See also:

How to deliver a Hall of Fame speech

The public speaking prospector

What’s your warm-up for a presentation?