The 7 Craziest Tax Deductions

Funny, Money, Taxes

Tax season is upon us once again, which means you’re probably getting ready to break out the old TurboTax or, if you’re lucky, your mild-mannered accountant is sharpening his pencils and dusting off his calculator on your behalf. Of course, paying taxes is necessary, but most of us don’t enjoy it, and we all hope to minimize the hit on our April cash flow. This is where deductions come in.

Not all deductions are created equal, however. Most of us comfortably deduct things like business dinners and home office expenses, but some take deductions to a whole new, crazy level. Every year, people—including accountants on behalf of their clients—claim deductions for mind-bogglingly nutty things.

We would caution against trying this on your own taxes. It more often than not ends badly, and we’d hate to see you slapped with fines and possibly jail time for trying to write off the family pooch or your Maxim subscription. So, while you do your taxes the old-fashioned way, here are the seven craziest tax deductions of all time:

The Sperm Deduction

A CPA in Massachusetts recounted the story of a man in his church who apparently thought very highly of his own DNA and ability to sire future generations—he planned to deduct the cost of having his sperm banked before having prostate surgery. “His reasoning was that the gift of his sperm was such a value to humankind that he should surely be able to take a tax deduction for it,” reported the CPA. Now that’s what we call hubris.

The Boob Job Deduction

Although you probably can’t justifiably deduct your chin implants or eye lift, a few people have successfully deducted certain procedures that directly affected their ability to make a living. Take Cynthia Hess, for example, an exotic dancer who convinced the IRS to accept her deduction for the depreciation of her breast implants. “Chesty Love,” as she’s known in the biz, pumped up her breasts to a ridiculous 56FF, claiming they significantly improved her career prospects. The Tax Court bought it—at 10 lbs. per breast, they were convinced there was no way she was getting any kind of personal benefit from them.

Likewise, a New York based-exotic dancer was successfully able to deduct the yearly costs of clothes, photos, makeup, tanning, teeth whitening, false eyelashes, and other beauty treatments because she was able to prove that the expenses directly impacted her business. Eventually she was audited, but the IRS allowed the deduction.

The Pole Dancing Deduction

Your business may benefit when you are happy and relaxed, but not all relaxation activities are considered deductible, even under the heading of “meals and entertainment.” Such was the case with the man who attempted to write off the $800 he spent on pole-dancing lessons for his wife, claiming that watching her dance after work improved his job performance. Luckily, his tax preparer caught it and was able to remove the claim before it went to the IRS. They probably would not have been amused.

The Recreational Drug Deduction

Rock stars may feel like they have to meet certain lifestyle benchmarks, but the IRS doesn’t always agree—especially in the case of the band who tried to deduct their illegal drugs under “travel and entertainment.” The band’s bookkeeper reasoned that the band’s recreational drug expenses were “necessary and ordinary,” but the CPA who filed their taxes disagreed. The most mind-boggling part of the story was that they didn’t even attempt to claim the drugs were prescribed or medically necessary, which would make them both legal and legitimately deductible.

The Bodybuilding Oil Deduction

Just as businessmen need suits and office space, bodybuilders need…oil. Bodybuilder Cory L. Wheir challenged the IRS when they declined his deduction for oil to grease up his body for competitions, and won. Tax Court ultimately approved the body oil deduction, but in the same hearing, they refused his deduction for the 3 lbs. of bison meat he consumed daily for muscle building. Apparently normal people, though un-oiled, eat bison, too.

The Deadbeat Brother Deduction

Does your deadbeat brother (or cousin or neighbor or ex-friend) owe you money? There’s a provision in tax law for writing off a bad personal loan of up to $3,000. The IRS won’t just take your word for it, though—you must provide a signed promissory note, proof that you attempted to collect, and an explanation as to why you don’t think you’ll ever see it from the borrower. Though you won’t ever get the full amount owed to you, deducting bad debts could save family Thanksgivings for years to come.