By Stacey Gorowitz, CPA, MBA

As the end of the year approaches, many of us are looking more intently at the things we spend money on and wondering which of them might possibly be tax deductible.

While it never hurts to scrutinize financial outlays with an eye for hidden deductions, it’s easy to stretch the bounds of realism in our zeal to minimize the tax bill we know is coming. On the other hand, maybe the dividing line between fantasy and reality isn’t where you’d expect to find it when it comes to deductibility. Here are some of the more unusual things the IRS has accepted as legitimate writeoffs in recent years.

• 

  Cat food. The resourceful couple who pulled off this one deducted the food they used to entice feral cats to their junkyard. While there, the cats also kept the facility more customer-friendly (and safer) by keeping down the population of snakes and rats that also liked the area.

• Body oil. If you’re a pro wrestler, greasing up those rippling muscles to wow the crowds during competitive events is apparently seen as a legitimate business expense. But no, you won’t be able to write off the steroids you’re secretly taking in hopes of boosting the buffness.
• Nose job. Hey, it’s for work! That’s true if you happen to be in the business of selecting and buying fine wines. The oenophile and wine store owner who successfully claimed this deduction got a doctor’s note explaining that the surgery was needed to correct a problem he was having that made it difficult to smell. How could he detect that desirable fruity bouquet with a hint of leather and a grace note of motor oil if his sniffer wasn’t in top form?
• Sex change operations. Now if you just have a hankering to view life through a different lens, this won’t count. Neither curiosity nor boredom qualify you for the deduction. However, if your doctor diagnoses you with Gender Identity Disorder, you go through the extensive therapy protocol and adopt a different gender identity publicly for the required year before the surgery takes place, you may deduct the cost of gender reassignment surgery from your taxes as a medical expense performed to correct a problem.
• Tuna fish. This brilliant maneuver involved annual fishing vacations taken in California. Each year, the savvy sportsman would deliver the hundreds of pounds of tuna he caught to a cannery that gave a religious institution the money raised by selling the fish. This qualified the fish as charitable deductions, and at the market price of around $5 a pound, that made for a very profitable series of vacations!

Considering some of the surprising things that the IRS has approved as deductible expenses, it may pay off to maintain a very open-minded stance as you look around for savings opportunities. By all means, be as creative as you can in your thinking about what might qualify, just don’t get carried away. The key is to have a fully defensible and logical reason why your desired deduction should count as legitimate reasonable business expense and to check with an extremely knowledgeable tax professional to make absolutely sure it passes muster. The last thing you want is to try to explain to an unsmiling IRS representative that “It sort of seemed reasonable at the time.”