AMF ADVISORS BLOG
Weirdest Tax Deductions Ever Approved
Cat food. Breast implants. A swimming pool. All nine of these were real deductions that a real tax court or tax authority actually approved — and every one of them is documented right down to the case number.
The rule that governs almost every business deduction — in the US, the UK, Canada, or anywhere else — boils down to a version of the same test: was this “ordinary and necessary” for your business, or was it really a personal expense wearing a business disguise? Most of the time that line is obvious. Every so often, someone takes it to court and wins in a way that sounds completely made up. It isn’t. Every case below is a real, citable ruling — not an urban legend recycled from another “weird tax facts” listicle. Read them for the entertainment, but take the underlying lesson seriously: unusual deductions are sometimes legitimate, but they need real documentation and a real business (or medical) reason behind them, not just a good story.
1. Cat Food, Deducted as Pest Control
A South Carolina junkyard had a snake and rat problem serious enough to endanger customers. The owners started feeding feral cats to keep the pests away — and deducted the cat food as an ordinary business expense. The IRS actually agreed and conceded the point: the cat food was doing a real job for the business, so it counted.
2. A Swimming Pool, Prescribed by a Doctor
Herbert Cherry’s doctor prescribed daily swimming to manage his severe emphysema. With no pool nearby that fit his schedule, he built one at home. The Tax Court allowed the pool’s heating, chemicals, insurance, and construction labor as medical expenses — though not every cost tied to it, since a couple of add-ons weren’t proven necessary for the treatment itself.
3. Posing Oil, Deducted by a Bodybuilder
Competitive bodybuilder Corey Wheir deducted the specialty posing oil that makes muscles glisten under stage lighting — a product sold only through bodybuilding trade publications, not to the general public. The Tax Court allowed it, on the reasoning that a product with no ordinary personal use is a legitimate business cost. His buffalo meat and protein shakes, on the other hand, got rejected — regular people eat those too.
4. Breast Implants, Depreciated Like Equipment
Performing under the stage name “Chesty Love,” exotic dancer Cynthia Hess deducted the depreciation on surgically enlarged implants as a business asset. The court’s reasoning was almost clinical: the implants were extreme enough to be useful only for her act, and were genuinely detrimental to her health and ordinary life — satisfying the same test used for a costume that’s unsuitable for everyday wear.
5. A Private Plane, for Checking on a Rental Property
A couple flew their own small private aircraft to inspect and manage a rental condo, then deducted the fuel and depreciation as rental-property expenses — even though it increased the paper loss on the rental. The Tax Court allowed it. It’s a good reminder that “unusual” and “disqualified” aren’t the same thing, as long as the underlying business purpose is real and documented.
6. Part of a DNA Test Kit, Deducted as Medical Care
In a genuinely modern example, the IRS ruled that the health-report portion of an at-home genetic testing kit — the part that analyzes genetic health risks — qualifies as a deductible medical expense. The ancestry-tracing portion of the same kit doesn’t count, since that’s not medical care. It’s a nice illustration that this area of tax law is still actively evolving, not just a relic of old court cases.
7. Cat-Fostering Expenses, as a Charitable Deduction
An Oakland attorney fostered dozens of cats at a time for a feral-cat rescue nonprofit and deducted around $16,000 in vet bills, food, and utilities as unreimbursed volunteer expenses. The court allowed the large majority of it — though it drew a hard line on anything over $250 without a written acknowledgment from the charity, a good reminder that even a legitimate deduction can get partly disallowed on paperwork technicalities alone.
8. Extra Food, Deducted as "Fuel" by a Bike Courier
A self-employed Toronto courier covering roughly 150 km a day on foot and by transit argued that the extra food and water his body needed was the human equivalent of gasoline for a delivery vehicle — and where a vehicle’s fuel would be deductible, so should his. Canada’s Federal Court of Appeal agreed with the principle, and the case later pushed the CRA to adopt a standard daily meal allowance for self-employed couriers.
9. Clarinet Lessons, to Fix an Overbite
One of the oldest entries on this list: a 1962 IRS ruling allowed a family to deduct their child’s clarinet lessons as a medical expense, because a dentist had prescribed the lessons specifically to help correct an overbite. It’s held up as a go-to example in tax literature ever since for just how literally the “medically necessary” test can be applied — provided you actually have the prescription to back it up.
Notice the pattern: every single one of these held up because there was real documentation and a real, provable connection to a business or medical need — not because the expense sounded odd. The same unusual deduction that wins in Tax Court with a receipt, a prescription, and a clear paper trail gets rejected instantly without one. If you’re ever tempted to write off something a little unusual, that’s exactly the moment to ask a professional first.
Not Sure What You Can (and Can't) Deduct?
You probably don’t need to deduct posing oil or a swimming pool — but you’re almost certainly missing legitimate deductions you don’t know about. AMF Advisors helps businesses across Canada, the UAE, and the UK find every deduction they’re actually entitled to.