The original version of this article was published on June 11, 2015. Back when the world was young and the health insurers still thought of as a fun new thing to try.

Sometimes you have to laugh a little to ease the stress of a busy work schedule. So, come on, take a break away from the many spreadsheets or calls that are in front of you, relax, sit back and laugh along with us.

We bring you a collection of some of the best insurance jokes that you can use to amuse your coworkers, your clients, and even to break the ice during a conference (just remember to take into consideration the content, context and intent of the joke, which should never insult anyone, unless you’re presenting a roast at Comedy Central). We have also included some of our reader comments and jokes in this article.

Know any good jokes that we missed? Leave them in the comments below.

Some jokes that our readers have posted in our comments:


1. That awkward moment when you deliver a highly rated life insurance policy…

“Whenever I deliver a highly rated life insurance policy, I remind the insured that while the premium may be higher, given their health, they won’t pay nearly so long! Then I smile and chuckle a bit, they chuckle too, and they accept the policy. Deep down, pretty much all people know what their health status really is … so don’t let ‘em blow smoke at you.”

- MrWiseOwl

2. Introverts vs. extroverts, and one correction

“What’s the difference between an introverted actuary and an extroverted actuary? An introverted actuary looks at his shoes when he talks to you. An extroverted actuary looks at your shoes . . .”

- Linda

To which another reader commented: “Oldest joke in the book except it is the difference between an actuary and an accountant.” – Never gets old

3. The real question is: Can your wife really get remarried?

“I was trying to deliver a life insurance policy to a fella who kept insisting to me that his wife could always get remarried. Finally, I blurted out ‘have you looked at her lately?’ He took the policy …”

- MrWiseOwl

4. What’s Hobby Lobby got to do with it?

“Question: What do accountants use for birth control? Answer: Their personality.”

- Robert

Insurance jokes from the internet


5. It’s all about the policy…

Would Transformers buy life insurance … or car insurance?

(From Photo: Actor Jack Reynor poses for photographers during a press conference for his film “Transformers: Age of Extinction.” AP Photo/Koji Sasahara)


6. Barn and husband insurance

Larry’s barn burned down and his wife, Susan, called the insurance company. Susan told the insurance company, “We had that barn insured for fifty thousand and I want my money.”

The agent replied, “Whoah there, just a minute, Susan. Insurance doesn’t work quite like that. We will ascertain the value of what was insured and provide you with a new one of comparable worth.”

There was a long pause before Susan replied, “Then I’d like to cancel the policy on my husband.” 



7. How to start a flood

A lawyer and an engineer were fishing in the Caribbean. The lawyer said, “I’m here because my house burned down, and everything I owned was destroyed by the fire. The insurance company paid for everything.”

“That’s quite a coincidence,” said the engineer. “I’m here because my house and all my belongings were destroyed by a flood, and my insurance company also paid for everything.”

The puzzled lawyer asked, “How do you start a flood?”



8. What’s in the bucket?

A man walks into an insurance office and asks for a job.

“We don’t need any one,” they replied.

“You can’t afford not to hire me. I can sell anyone anything anytime.”

“We have two prospects that no one has been able to sell. If you can sell just one, you have a job.”

He was gone for about two hours and returned and handed them two checks, one for an $80,000 policy and another for a $50,000 policy.

“How in the world did you do that,” they asked.

“I told you I’m the world’s best salesman, I can sell anyone anywhere anytime.”

“Did you get a urine sample?” they asked him.

“What’s that?” he asked.

“Well, if you sell a policy over $40,000 the company requires a urine sample. Take these two bottles and go back and get urine samples.”

He was gone for about eight hours and then he walks in with two five gallon buckets, one in each hand. He sets the buckets down and reaches in his shirt pocket and produces two bottles of urine and sets them on the desk and says, “Here’s Mr. Brown’s and this one is Mr. Smith’s.”

“That’s good,” they said, “but what’s in those two buckets?”

“Well, I passed by the school house and they were having a state teachers convention and I sold them a group policy!”



9. Honoring the last wish…

A father told his three sons when he sent them to the university: “I feel it’s my duty to provide you with the best possible education, and you do not owe me anything for that. However, I want you to appreciate it; as a token, please each put $1,000 into my coffin when I die.”

And so it happened. The sons became a doctor, a lawyer, and a financial planner, each very successful financially. When they saw their father in the coffin one day, they remembered his wish.

First it was the doctor who put ten $100 bills onto the chest of the deceased.

Then came the lawyer, who put a $1,000 bill there, too.

Finally, it was the heartbroken financial planner’s turn. He dipped into his pocket, took out his checkbook, wrote a check for $3,000, put it into his father’s coffin, and took the $2,000 cash.



10. That’s one way to pay those hospital bills …

Mr. Smith was brought to the hospital and taken quickly in for heart surgery. The operation went well and, as the old man regained consciousness, he was reassured by a Sister of the hospital, who was waiting by his bed.

“Mr. Smith, you’re going to be just fine,” said the nun, gently patting his hand. “We do need to know, however, how you intend to pay for your stay here. Are you covered by insurance?”

“No, I’m not,” the man whispered hoarsely.

“Then can you pay in cash?” persisted the nun.

“I’m afraid I cannot, Sister,” he said.

“Well, do you have any close relatives?” the nun questioned sternly.

“Just my sister in New Mexico,” he volunteered. “But she’s a humble spinster nun.”

“Oh, I must correct you, Mr. Smith. Nuns are not spinsters; they are married to God.”

“Wonderful,” said Mr. Smith. “In that case, please send the bill to my brother-in-law.”


window washer

11. Fast customer service

Three insurance salesmen were sitting in a restaurant boasting about each of their companies’ services.

The first one said, “When one of our insureds died suddenly on Monday, we got the news that evening and were able to process the claim for the wife and had mailed a check on Wednesday evening.”

The second one said, “When one of our insureds died without warning on Monday, we learned of it in two hours and were able to hand-deliver a check the same evening.”

The last salesman said, “That’s nothing. Our office is on the 20th floor of a tall building. One of our insureds, who was washing a window on the 85th floor, slipped and fell. We handed him his check as he passed our floor.”



12. JCPenney sold insurance?!

As part of its direct marketing program, JCPenney sells life insurance over the phone. One of the oddest events these telemarketers had was when they received a phone call from a person wanting to buy life insurance. The person who answered the phone began writing the sale as she normally would, until she got to the new customer’s residence; he was on death row, due to be executed the next day. She had to decline the sale.


wild west

13. It had to be snakes

The insurance agent was questioning the cowboy who had applied for a policy.

“Ever have an accident?” he inquired.

“Nope,” the cowboy answered.

“Not even one?” asked the agent, incredulously.

“Nope,” the cowboy insisted. “Rattler bit me once, though.”

“And don’t you call that an accident?” exclaimed the amazed agent.

“Nope; the danged varmint done it a-purpose.”



14. To jump or not to jump?

An actuary and an underwriter are watching the eleven o’clock news. A story comes on involving a man on a window ledge threatening to jump.

The underwriter says, “I’ll bet you fifty bucks he doesn’t jump.”

The actuary says, “I’ll take that bet.” A few minutes later the guy jumps.

As the underwriter reaches for his wallet, the actuary says, “Never mind. It’s not fair. I saw it on the six o’clock news.”

The underwriter responds, “So did I, but I just did’’t think it would happen twice.”



15. Actuary, underwriter and salesperson riding in a car

An actuary, an underwriter, and an insurance salesperson are riding in a car. The salesperson has his foot on the gas, the underwriter has his foot on the brake, and the actuary is looking out the back window telling them where to go.



16. Lashing out

A broker, an actuary and an agent are all caught drinking smuggled liquor while staying in Saudi Arabia. Under Saudi law, simply possessing alcohol is an offense punishable by death.

However, the local prince is feeling generous that day, so he commutes the death sentence and instead sentences each to 20 lashes. After further thought, the prince does not want to offend the American government, so he also grants each a wish to ease their suffering.

The broker is punished first because he drank the most.

“What is your wish?” asks the Saudi prince.

“I’d like to have a pillow on my back,” replies the broker. So a pillow is placed on his back, and the punishment begins. The pillow holds up for about 10 lashes, after which the broker screams out in pain.

The actuary had only a few drinks, so he is punished next.

“I’d like to have two pillows on my back,” boldly states the actuary. So two pillows are placed on his back, and the punishment begins. The pillows hold up for about 15 lashes, after which the actuary screams out in pain.

Finally, the agent steps forward. Of the three, he was the only one who didn’t drink. The Saudi prince is impressed by this, and grants him two wishes.

The agent then states, “Well, for my first wish, I want to receive 100 lashes, not 20.”

“Your courage is impressive,” states the prince. “And for your second wish?”

“Strap the actuary onto my back,” replies the agent.



17. Does marrying an insurance agent prolong life?

A woman was in the hospital after feeling very ill. The doctor says to her, “I have some bad news for you. You only have three months to live.”

“Oh that’s terrible,” the woman sighs, “What am I going do?”

The doctor replies, “Marry an insurance agent.”

“Will I live longer?” asks the woman.

“No,” replies the doctor, “but it will SEEM longer.”



18. Life insurance for a centenarian?

When a marketing officer asked an actuary why he recommended selling more life insurance policies to 98-year-olds, the actuary replied, “According to our tables, very few of them die each year.”



19. Selling to a ghost?

Q: What is the hardest thing to sell to a ghoul? 

A: Life insurance! 

(From a NSFW website:


20. Spiders know best

Female spiders eat the male spiders after mating. They know collecting life insurance is easier than child support. 

(From a NSFW website:

old man

21. Waiting to exhale

My wife and I took out life insurance policies on each other — so now it’s just a waiting game. 

(From a NSFW website:


22. The changing of a light bulb

Q. How many actuaries does it take to change a light bulb?

A. How many did it take last year?



23. It’s all about GI insurance

Airman Jones was assigned to the induction center, where he advised new recruits about their government benefits, especially their GI insurance. It wasn’t long before Captain Smith noticed that Airman Jones had almost a 100 percent record for insurance sales, which had never happened before. Rather than ask about this, the Captain stood in the back of the room and listened to Jones’s sales pitch.

Jones explained the basics of the GI insurance to the new recruits. And then said: “If you have GI Insurance and go into battle and are killed, the government has to pay $200,000 to your beneficiaries. If you don’t have GI insurance, and you go into battle and get killed, the government only has to pay a maximum of $6,000.”

“Now,” he concluded, “which bunch do you think they are going to send into battle first?”



24. Je suis Canadiens?

In Canada, there is a group of people who refuse to speak English. They’re called separatists and tend to live in Quebec. In the United States, they’re called actuaries.



25. A lying machine that can’t lie

An electronics firm invented a new machine, the Excuser, designed to come up with creative and convincing excuses. Aimed at people who are perennially late for work, or forget their wives’ birthdays, or the like. This was a fairly expensive new product launch, so they took out an insurance policy against unforeseen product defects. They launched the machine with much fanfare.

Unfortunately, a problem did develop. The system would always give the boss the real reason why the person was late, and turned out to be no good at inventing false ones. This made volume sales somewhat unlikely, and so the company went to its insurer to claim for the losses they’d made. The insurance company listened to the story, and checked the policy terms. The representative came back to the electronics company and said: “Sorry, but you’re not covered for product lie ability.”



26. On getting the job …

A man was applying for a job as an insurance salesman. The form requested prior experience, so he wrote “lifeguard.” When the manager met him, he said, “We are looking for someone who can sell himself. How does working as a lifeguard pertain to salesmanship?” The man replied, “I couldn’t swim.”  

Needless to say, the man got the job.


27. Can an actuary get deactivated?

If irreverent priests are defrocked, and dishonest attorneys are disbarred, shouldn’t difficult actuaries be deactivated?



28. Off to the races!

A life insurance agent decides to take a good friend with him to the horse race track and enjoy the afternoon. When he returns home his wife asks, “How was your day and did you make any money?”

He replies, “Well, I didn’t make any money today, but my client sure learned how gambling with the numbers certainly doesn’t pay off.”



29. Playing doctor

The seven-year-old girl told her mom, “A boy in my class asked me to play doctor.”

“Oh, dear,” the mother nervously sighed. “What happened, honey?”

“Nothing. He made me wait 45 minutes and then double-billed the insurance company.”



30.  Having hundreds of clients …

An insurance agent said to a customer, “Thank you, Mr. Barricks, for your patronage. I wish I had 20 clients like you.”

“Gosh, it’s nice to hear that, but I’m kind of surprised,” admitted Mr. Barricks. “You know that I file many claims and always pay my premiums late.”

The insurance agent said, “I’d still like 20 clients like you. The problem is, I have 200 like you.”



31. Living to 100?

A grandmother was in her late 90s and decided to move to Florida. As part of the preparations, she went to see her doctor and get all her charts. The doctor asked her how she was doing, so she gave him the litany of complaints: this hurts, that’s stiff, I’m tired and slower, etc.

He responded with, “You have to expect things to start deteriorating. After all, who wants to live to 100?”

The grandmother looked at him straight in the eye and replied, “Anyone who’s 99.”



32. These are the 4 things you can’t recover in life

1) The stone………..after it’s thrown,

2) The word…………after it’s said,

3) The occasion……after it’s missed, and

4) The time………….after it’s gone.


See also:

7 more great accountant jokes

20 of the best insurance jokes

7 great accountant jokes