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6 Ridiculous Tax Writeoffs (That Didn’t Work)

Even reality TV doesn’t give justice to the real world and the funny, eye popping, or jaw dropping events that happen every day that very few people hear about. If your job involves working with the general public in any capacity you probably have stories that all of us would love to hear but since it’s tax season, I scoured the internet to find what I thought were some of the most “unique” (how’s that for politically correct) tax stories worth telling.

And before you start laughing, remember that given what our tax rates [3] our, it’s no surprise people are trying to reduce their liability – but claiming one of these ridiculous tax writeoffs is the wrong way to go about that!

The Condo

A lot of people have second homes, right? Especially if you’re one of those who likes Florida in the winter and northern states in the summer, two homes isn’t that odd. Bankrate [4] tells the story of the tax professional who was meeting with a couple and ask the gentlemen about the mortgage interest for the condo in Utah. Judging by the wife’s face, she didn’t know that they owned a condo in Utah. You can fill in the blanks as far as who lived there.


We would all like to think that our hobbies are write offs but in most cases, they aren’t but that doesn’t stop people from trying. A New York CPA [5] was working with a client who was a Hollywood set designer and naturally a big movie buff. According to him, buy and renting movies was research that related to his line of work. NOPE!

Depletion Allowance for That?

Unless you’re a mine, oil, or other business owner who loses money as more product is removed and sold, you probably don’t have any use for the depletion allowance. One man [6] believed that he was entitled to the depletion allowance for one of his sources of income. He was a sperm donor.

The Livestock Deduction

A Texas rancher [7] was audited by the IRS for expenses relating to 20 animals he had listed as breeding stock. The auditor asked him, “I assume you breed these animals yourself?” The old rancher answered, “No, I’ve got a bull for that.”

The Amish?

If you’re Amish, claiming your buggy [5] as a work expense is far from out of the ordinary and in fact quite common. But what if the buggy got a pimp-my-ride style makeover? The Amish way of pimping a buggy may not include pinstripping, a few subs in the back seat, and an Xbox but this buggy had a velvet interior, tinted windows, kick plates, and like the pimped cars of today, some sweet hydraulics. Hydraulic brakes! The standard cost of the buggy was a writeoff but not the “extras.”

The Home Office

Home office deductions [8] are complicated because you can only deduct the expenses that occur in the office. If the office is 10% of the total size of your home, you can only deduct 10% of the expenses. One person who worked from home wanted to deduct the cost of the toilet paper he used for his home as a home office expense. “You could do it”, said the person’s CPA, “ but you’ll need to know what percentage of each roll was an expense relating to your business”.

How about You?

Are you a tax professional? Post your funniest tax stories below. We can all use a good laugh at tax time.