The Most Outrageous and Unexpected Tax Deductions

tax16Breast Implants

In 1988, exotic dancer "Chesty Love" underwent several procedures at the urging of her agent to enhance the size of her breasts.

Although her earnings almost doubled after the procedures, her chest had become so massive -- a size 56FF -- that she suffered medical problems.

The court ruled that her plastic surgery was "incurred solely in the furtherance of the business engaged in" and "incurred in producing revenues to the business," she was entitled to deduct the cost of her implants (Hess v. Commissioner, 1994).

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tax3Nose Job

A wine store and wine bar owner from California who was having trouble smelling was able to write his nose job off as a business expense last year.

He claimed that his annual buying trips to Europe  required him to be able to smell in order to pick out the best wines for his business.

After getting the green light from his tax preparer, he was told to get a note from his doctor about the smelling condition and also a prescription for the nose job in case the IRS came around.

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Tax4Air Conditioning

Tom Walpole, a CPA from Rochester, tells the story of a client who was able to successfully write off over $10,000 for central air conditioning in his home and cottage.

The client claimed the purchase as a medical expense, deemed necessary by a condition that involved excessive sweating, which required him to have air conditioning.

Attached to this claim was a doctor's prescription stating that the loss of fluids from sweating could pose a health threat to the man.

Surprisingly, the IRS allowed the deduction.

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tax6'Work Trip'

This one is really a stretch.

The owners of a Dairy Business went on an African Safari and claimed the vacation as a business expense, justifying the visit by stating that much of the dairy's promotional activities and marketing efforts involved wild animals.

That, we get. But a safari? Come on.

The IRS deemed the trip "ordinary" and "necessary" and let it slide.

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tax20Sex Toys

Vincent Porter, a CPA from Arlington, Texas had a client who was an exotic dancer.

Through her webcam work she was able to deduct the cost of lubricant, lingerie, and a few vibrators.

"If a roofer can deduct the cost of his tools used in his line of work, then an 'actress' may deduct her 'tools' used to generate revenue as well," Porter said.

"As long as she was not doing anything illegal, then we could support the deduction."

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It's a gutsy move to claim beer as a business expense if you don't own a bar or a restaurant... or anything related to the food industry.

A gas station owner successfully wrote off the free beer he gave to customers as a business expense. He did end up in tax court but the final verdict ruled in his favor.

In an interesting and unfair twist, an Oklahoma businessman who essentially did the same thing by claiming several cases of whiskey he gave to his clients as "entertainment" was denied.

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Frustrated by a lack of interest in his failed furniture business, a Pittsburgh man decided to hire someone to burn his store down.

For the destruction of his business he pocketed $500,000 from the insurance company. He pushed his luck a step further when he deducted the $10,000 paid to the arsonist as a consulting fee.

Two years later an IRS audit resulted in both men going to prison.

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tax11Swimming Pool

A sick emphysema patient was told by his doctor that he needed to start exercising. The man decided to build a swimming pool in his backyard.

He then deducted the cost as a "necessary medical expense."

Surprisingly enough, the IRS actually agreed with the deduction and paid for the pool, cleaning chemicals, heating, and maintenance.

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tax12Cat Food

The owners of a junkyard decided to fix an ongoing rodent and snake problem by setting out bowls of cat food to attract the neighborhood felines.

The cats not only devoured the pet food, but also the undesirable creatures, making the junkyard safe for customers.

The pet food actually counted as a business expense and was successfully deducted.

(Image via Flickr)

tax17Criminal Lawyer Fees

A NYC man was pulled over on his motorcycle and arrested for carrying a knife.

He deducted his criminal lawyer fees as a business deduction, and for good reason too. It turned out he was an actor and had been on his way to a performance, in which the knife was a mandatory prop for the play.

The IRS audited his return but he won the deduction.

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