Tax time can be very frustrating when you realize you’re not going to get as big of a refund as you were expecting, or worse, you’re going to have to send the IRS a check. So it’s no wonder people might ask if their pet counts as a dependent (it doesn’t) or if they can write off that new suit jacket (probably not).

Deductions are the taxpayers chance to hold on to their money and people will go to extreme lengths to justify some pretty crazy expenses. Most of these attempted write-offs fail, but sometimes the just-so-crazy-it-might-work deductions go through and make their way into tax-season legend.

Body Oil

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It’s not easy to be a professional body builder. If you want to win, you have to eat healthy, work out non-stop and, of course, oil yourself up to a brilliant shine. That’s what Corey L. Wheir argued on his tax return, at least. Since his income depended on winning competitions and oil directly enhanced his ability to earn those winnings, the tax court allowed him to include it as a deduction.

Charity Meat

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If you’re a deer hunter who’d like a few more deductions on your taxes, just move to South Carolina. The state provides for a $50 tax deduction for every deer carcass that an individual donates to charity.

Really, Really Large Breast Implants

breast implants
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Generally speaking, cosmetic surgery can not be written off. However, an exotic dancer who goes by the stage name Chesty Love was able to convince the tax courts that she should be allowed to deduct the cost of her 56N implants as a business expense, as they were necessary to increase the size of her… tips. Given the exceptional size of the implants, the IRS deemed them to be useful only for business purposes and a write-off.

Cat Food

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Your cat depends on you to feed it, so you should get to write off the cost of that Meow Mix, right? Not unless you own a junkyard like Samuel and Carol Seawright did. The Seawrights successfully argued that in order to keep their business operating, they required cats to chase the rats away, and therefore feeding cats counted as a business expense.

Clarinet Lessons

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In the 1960s, a woman successfully claimed the cost of her son’s clarinet lessons as a deduction because the child’s orthodontist claimed the lessons were helping to correct the child’s overbite. Unfortunately for parents everywhere, piano lessons and soccer practices still don’t count.

Swimming Pool

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In most cases, adding a swimming pool to your home might increase the value, but won’t increase your tax deductions. However, if you have a note from your doctor prescribing water therapy as a necessary medical procedure, you just might be able to write off that backyard beauty.

Pirate’s Ransom

'Pirates of the Caribbean'
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In case you’re attacked on the high seas and forced to pay you’re way free, don’t worry. All is not lost. You can just deduct the cost on your taxes. You will want to have back-up documentation to prove this to the IRS, of course, so if you’re able to, ask Captain Jack to draw up a treasure map of the stolen booty.

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