Top 10 Insurance Jokes

Humour is a very subjective topic. It’s the same as art — what one person finds entertaining might sound dull or even offensive to another. The insurance business in general is not an area that most people would find funny, so we took some extra time to put together something that’s really worth it!

This article is a collection of (in our opinion) the most entertaining jokes, anecdotes, and cartoons we were able to dig up. Making a top 10 was a very intensive job — there might be thousands of jokes out there that we never heard of and that are funnier than any in this article.

So if you know any insurance jokes that you feel should have been in this article or you have any kind of funny stories you’d like to share, feel free to contribute to the discussion below.

Now relax, read, and hopefully laugh. The jokes are on us!

John Morris

This is the work of John Morris, native of Wales, UK. Morris was an employee of a Birmingham car factory, later in Detroit and Cleveland. He drew cartoons in his spare time and later realized that it’s much more profitable than his full-time job. So he quit and pursued the career of a professional cartoonist. He’s widely recognized for his cartoons focused on business, and his work is known around the globe.

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?”

Robert Leighton

American cartoonist Robert Leighton is also known for his writing, book illustrations, and passion for puzzles. He is the co-founder of Puzzability, a puzzle writing company. His single-panel cartoons have appeared in The New Yorker, the Wall Street Journal, and other periodicals.

One day, an American life insurance company received a letter from a lady saying that, unfortunately, they have to cancel her husband’s life insurance policy. “We always paid it on time,” she wrote, “but since my dear husband’s sudden death last year, we have had some financial hardship. So we would like not to pay it anymore.”

Randy Glasbergen

Randy Glasbergen is probably one of the most published cartoonists in the U.S. He’s most recognized for his daily comic The Better Half. Randy is a freelancing author who began his career at age 15, and his works are well known around the world. In addition to his newspaper and magazine publishing, his work includes cartoon books, illustrations, greeting cards, and even instructional books on drawing cartoons.

If you sleep with your wife, that’s Legal and General.
If you sleep with your girlfriend, that’s Mutual Trust.
If you sleep with a prostitute, that’s Commercial Union.
If you sleep with all types, that’s Group Life.
If your wife lets you sleep around, that’s Liberty Life.

Dan Rosandich

Talented world-class cartoonist Dan Rosandich is a native of Detroit, Michigan. Throughout his career, he has contributed to magazines and newspapers like Reader’s Digest, The National Enquirer, The Saturday Evening Post, and Britain’s The Sun. He is also well recognized for his work on the Chicken Soup For the Soul book series.

A super genius goes in to see a doctor. “Doc,” the genius says, “I think I’m too smart. I’m having trouble even communicating with people because we have no common frame of reference, and it’s ruining my social life. Can anything be done?”

The doctor runs a series of tests on the genius, and indeed finds that he is too smart. He says, “Currently, your IQ is 250, which is vastly superior to an average man. This is why you are having trouble communicating. I do have a cure, however. I have a machine that will drain away some of your intelligence, leaving you with an IQ of 160. You’ll still be a genius, but you should be able to lead a normal life as well.”

The genius immediately agrees to the treatment, so the doctor straps him into the machine.

Just as the doctor turns on the device, he gets a phone call from his ex-wife. They have a heated phone conversation for several minutes before the doctor remembers his patient. He rushes back, and is shocked when he sees the IQ readout at 75.

The doctor says, “Are you all right?”

The former genius just stares blankly.

The doctor shakes him, saying, “Say something.”

The former genius replies, “Can I interest you in a life insurance policy?”

Marty Bucella

Cartoonist Marty Bucella is a former student of geography, though he never pursued this career. After a troublesome start, his career in drawing cartoons took off, and Marty’s works are well known mainly to readers of The Saturday Evening Post, where he focused mainly on medical topics. He has also been featured in various other magazines, newspapers, ads, and websites.

Last night as I lay sleeping, I died, or so it seemed,
Then I went to heaven, but only in my dream.

Up there, St. Peter met me, standing at the pearly gates,
He said, “I must check your record, please stand here and wait.”

He turned and said, “Your record is covered with terrible flaws,
On Earth, I see you rallied for every losing cause.

I see that you drank alcohol and smoked and used drugs too.
Fact is, you’ve done everything a good person should never do.

We can´t have people like you up here, your life was full of sin,”
Then he read the last of my record, took my hand and said, “Come in.”

He led me up to the big boss and said, “Take him in and treat him well,
He used to work in insurance. He’s done his time in hell.”


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  • Chuck Groot
    April 5, 2014 at 3:50 pm

    Thanks Chantal!
    We all need a good laugh and more often.
    Even at our own expense lol.

    • LSM Insurance
      April 6, 2014 at 1:56 pm

      Agreed. Glad you enjoyed it Chuck!

  • jamesfranklin
    December 12, 2013 at 1:46 am

    Last one is just amazing.. good sense of humor in financial sectors ..

    Soon we will have this kind of topic in our blog