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Using Humor In Sales Letters to Charm and Disarm

kid on turtle

Often, if you try to be funny when writing a sales letter, bad things happen.

More often than not, your jokes will fall flat, as folks tend to skim, not read, and they often just miss the information that is necessary to fully grasp your brilliant, witty prose.

As a result, the reader feels stupid, or is simply confused, and you know what that means ... into the trash bin you go.

So that’s the rule.  But since rules are meant to be broken, let’s have a look at those deft practitioners who have pulled off sales letters with humor successfully.

Below is a letter I received recently via email from a new start-up company that makes colorful pieces of plastic which wrap around your iPhone.   The goal is to get you to become their fan on Facebook.

The product itself appears to be utterly unremarkable, however, the copy that thanks you for purchasing this little slab of plastic for one penny -- Did I mention the offer was great? -- makes it seem as if you could be holding The Sorcerer’s Stone.

Let’s have a look:

Dear Early Adopter / Guinea Pig / Josh Manheimer,

Thank you for robbing DefaultCase blind by ordering an iPhone case for $0.01!

With any luck, you will receive your DefaultCase within 1 - 2 weeks. It will arrive by courier pigeon or USPS, but very soon our patent-pending teleportation technology should speed up the process to 3 days or less.

DefaultCases cost more to produce than $0.01. This is okay with us because you are cool. We know this (about you being cool) because you will have a DefaultCase and by default will become cool.

As an early adopter of our product we greatly appreciate help getting the word out. Tell your friends and family how cool we say you are and tell them how uncool they are if they do not join you in our plot to take over the iWorld.

If you do not like your DefaultCase, please destroy it using a microwave or explosives (our lawyers say nay) and tell everyone that we suck.

If you are tempted to pick up another case, go for it. Order as many as you want as long as you use them. Give them as gifts. You can use them to buy friends for less than ever before! Send us feedback and/or Ramen Noodles.

P.S. One more thing - Click "Invite Your Friends" on If you invite lots of friends you will (probably) go to heaven.


Ryan M. Pamplin
Chief Executive Officer
Ryactive Corp. (Parent of DefaultCase)

After your plastic Default Case arrives (I ordered two), you are greeted with yet another letter which piles on the charm:

default case letter

The cumulative effect of this disarming tactic?

You pat yourself on the back for buying from such a smart, hip company.  And you wonder how can these people pay for their lattes at Starbucks selling iPhone cases for one cent each?

Then you remember, this is why God invented an extra fee for shipping and handling.

And now you wonder, “Who is really having the last laugh?”


Josh Manheimer
Norwich, Vermont

P.S.  Do you have your favorite examples of humor used in sales letters?   Now is the time to share with the group.

Princess Di and a Cat With A $200,000 Trust Fund

rich kitty

Not long ago I was asked to help our nation's premiere estates attorney, Herbert E. Nass, get media recognition for his new book.  This PR pitch letter prompted Terry Savage of The Chicago Sun-Times to write back and say, "This, without doubt, gets the award for the BEST PR PITCH . . ."

Here's what I wrote ...

This is about the world's richest pets ... Princess Di's bone-headed estate-planning blunder ... how a probate judge can give all your money and possessions to YOUR WORST ENEMY ... and my friend, Herb.

Dear Terry,

Hi!  As folks make their New Year's resolutions and hope to get their financial and estate planning house in order before April 15th, your audience might like to know about ...

... the world's richest pets and their million-dollar trust funds ... the estate attorneys who represent them ... and the relatives who stand to make a fortune if--God forbid--their furry, feathered, fiduciary "friends" should come to a premature end.

(I, personally, will volunteer to soothe the ruffled feathers of the oligarch parrot who suffers from clinical depression as a result of the stock market crash, but I digress...)

Anyway, a number of years ago, my high school buddy, Herb, represented a cat named Ming with a $200,000 trust fund.

You see, Ming’s owner had passed away, and it was Attorney Herbert E. Nass’s job to make sure all of Ming’s pet food, medical care, and catnip were provided for during Ming’s lifetime.

When Ming finally went to kitty heaven at age 10, the trust dictated that the remaining funds would go to Ming’s caretaker, a doorman in Ming’s building.

However, because Attorney Nass needed to make sure Ming’s death was not the result of foul play, he arranged for an autopsy which confirmed Ming had indeed passed away from natural causes.

With the coroner's report in hand, Attorney Nass was able to deliver the substantial balance of funds to the doorman and his family.

In this case, everything went according to plan.  However, unless you know all the possible pitfalls of estate law, things can go wrong.

Really wrong.

That's why Herb has just written a new book called, "The 101 Biggest Estate Planning Mistakes" where he assembles every bone-headed blunder ... foolhardy foul-up ... and chowder-headed mistake he has seen in his renowned, 25-year career as an estate attorney for the rich and famous.

Take Hotel Queen, Leona Helmsley, who left $12,000,000 to her dog named Trouble.  Unfortunately, for the pooch, the Queen of Mean made the bone-headed blunder on page 228.  As a result, her Maltese got a $10,000,000 haircut.

Take legendary artist, Andy Warhol, who left behind an estate of $500,000,000.  Because Warhol made one common, chowder-headed mistake (found on page 180), the foundation formed after his death was allowed to open a museum to honor the legendary New York artist ... in Pittsburgh!

Take Princess Diana.  Her two sons, William and Harry, could have avoided Britain’s 40% estate tax (approximately $14 million) had the attorneys for the former Princess of Wales not made the bungling error found on page 230.

Take oil baron, John Paul Getty who requested that his body be immediately buried on his private ranch after his death.  Unfortunately, because his legion of fancy lawyers neglected to follow the steps on page 223, Getty’s body was first embalmed and refrigerated at the Forest Lawn Memorial Park cemetery ... for three years!

Take multi-millionaire Wall Street mogul, R. Theodore Ammon.  Unfortunately before he was murdered, his high-priced New York law firm did not think to update his Will to reflect his bitter divorce proceedings.  As a result his wife, Generosa, who re-married the murderer, was entitled to almost everything.  Page 105.

Note:  Generosa did not make the same mistake years later.  When Generosa passed away, her Will left her jailbird husband, nothing.  Page 109.

Which bone-headed blunder can cost your estate millions in taxes while you’re alive and thousands in penalties after you pass away?

Which foolhardy assumption practically guarantees the probate judge will throw out your Will and possibly hand your most prized possessions to ... your worst enemy!

Which bungling foul-up can cause the IRS to suck away your estate even before you die?

No doubt, your audience would love to know -- before they keel over!

And learn from Attorney Nass how to prevent disgruntled relatives from making your Will “disappear” (page 52) or ...

...the inexcusable dumb error attorneys made when drafting Anna Nicole Smith's Will (page 124) ...

Well, so far I've given you just a taste of what you'll find inside Herb's new book, "The 101 Biggest Estate Planning Mistakes."

However, if you'd like to speak with Herb yourself, well, I’ll just have to make sure he is not in with a client (at $595/hour) that growls, purrs, barks, hisses, or sits perched on his shoulder.

Alas, each year it seems the Nass clientèle gets just a little furrier or more feathery.

I look forward to hearing from you.


Josh C. Manheimer
Norwich, Vermont

Crooks Study Fermat's Theorem to Dodge Jail Time

Community Service Help

Every once in a while I'm asked to help a client get some media attention.  Rather than send out a traditional press release, I prefer to write personalized pitch letters.

Here's one recent example:

This is about how crooks, who never graduated high school, are completing their court-ordered community service by studying Medicare Sustainability, Fractional Reserve Banking, and Partial Derivatives of Vector Valued Functions from the comfort of their home computers.

Take Lou. After the judge ordered him to perform 100 hours of community service for walking out of a department store with toys stuffed down his sweatpants, he had a choice.

Clean public toilets with a thick wire brush?

Study Napoleon’s Peninsular Campaigns online?

You see, even though Lou never made it past the sixth grade, he now could stay out of the slammer by studying Fermat's Theorem, the problems with mortgage-backed securities, and why the seasons are not dictated by the earth’s proximity to the sun.

While others were picking up trash along the Interstate with a spike, Lou’s girlfriend massaged his shoulders as he kindled a new interest in colon dysplasia, the refraction of seismic waves, and the fine points of strong acid titration.

In fact, all across the United States, judges are ordering community service for DUI’s, marijuana possession, and simple assault while their defendants -- with tattoos on their massive forearms and barbells in their tongues -- are fulfilling their obligation to society by studying the American-Chinese Debt Loop and Plate Tectonics.

The mastermind behind this novel restructuring of how we mete out justice is an innovative entrepreneur named Adam Young. Today, his organization, Community Service Help, is the only entity in the United States whose sole purpose is to help you partner with a charity in your state and complete your court-ordered, community service online -- for only forty-nine bucks! To date, Young has helped thousands of individuals fulfill over 200,000 hours of service and, as a result, has raised over $50,000 for charities in the last year alone.

If you’d like me to introduce you to Mr. Young, so you can learn more about how his clients around the country have traded in a mop and a bucket for the thrill of learning carbon dating or how to measure death probability, don’t hesitate to get in touch.


Josh C. Manheimer
Norwich, Vermont

The Pilot -- The World's Best Sales Letters

It’s late.  You’re stranded between flights.  Two magic words can force the airline to book you a hotel room at their expense.  Who will tip you off to those crucial words?  Not the airline.

Did you know one of Vermont’s best restaurants is in the back of an old school bus?  Do you know where the bus is parked?

“I’m sorry to inform you,” the curator said, “but this is a fake.  Worthless.  A well-crafted forgery” -– and then he proceeded to chop a $1,000,000 painting into shreds with an axe …

Dear Direct Marketing Colleague:

Letter leads.  They can make or break your marketing campaign.

Their job is to stick like old chewing gum.  Slide down like Jell-O.  And introduce you to the offer like a Southern hostess at Christmas time.

For over 25 years, I’ve had the fun challenge of writing letter leads that grab readers by each eyeball and then … yank them right out of their sockets!

Now, with your permission, I invite you to join me as we hunt down the world’s best sales letters, hold them up to the light, examine their parts, and see how they glisten.

It’s my hope the conversation will be at a such a high level, and contain information so explosive, it should be labeled, “TOP SECRET!”

Over time, we’ll examine brush strokes from legendary copywriters of the past like Bill Jayme, Linda Wells, Hank Burnett ... and those who continue to leave their indelible mark in the present ... Judy Weiss, Richard Armstrong, Ken Sheck ...

And, of course, during the months ahead, I’ll reach into my own vault and pull out some of my controls that rocked the direct mail industry to its molten core.

Here is the now legendary lead for Rodale Press that became the most successful direct mail package in the history of their book division.

Here are the inspiring opening words for MORE MAGAZINE that became the most successful direct mail package in the history of the Meredith Corporation.

Here is the throat-grabbing lead for COOKING LIGHT that beat out the great Bill Jayme (the “Tiger Woods” of copywriters) and pulled 10.5%!

What will you get out of this adventure?

Well, if you’re an internet entrepreneur or a marketing executive, you will instinctively recognize the underlying structure behind an award-winning promotional letter and how to inspire others to creative genius.

If you’re a student of the art of written persuasion, you’ll understand with a seer’s clarity how I craft letters other copywriters brazenly steal from … and would sell their mothers to write.

“I’ve never written a fan letter to a fellow DM copywriter before,” wrote copy guru Bob Bly.  “But your new subscription letter for WRITER’S DIGEST is super.”

“Your ‘Trigger’ package is perhaps the perfect direct mail package,” wrote dm copywriter, Richard Armstrong.  “It should be in a vacuum-sealed glass case somewhere.”

So let us begin.

I will go blow the dust off some of the great controls in my file cabinet while you root out the treasures that you find in your travels.

Meet you back here soon.

Josh C. Manheimer
Norwich, Vermont