Ah, tax season—the only time of year when people willingly do math and accountants become more sought-after than Beyoncé tickets. While most of us are busy trying to figure out whether we can deduct printer ink or that one networking coffee meeting from 2023, some people have managed to outsmart the tax code in the most bizarre ways imaginable—and won.
Yes, folks, welcome to the IRS Comedy Hour, where real people have successfully deducted everything from cat food to body oil. If you’ve ever felt guilty about writing off your home office, don’t worry—these people deducted an ostrich and got away with it.
Let’s dive into 10 of the strangest tax deductions ever approved by tax courts.
The Guard Dog Tax Break – “Ruff Returns”
One business owner successfully deducted the cost of their guard dog’s food, vet bills, and training, claiming the animal was an official “security system.” The tax court agreed, meaning you can apparently write off your pet if it looks intimidating enough.
✅ Approved! If your dog can double as a bouncer, you might be sitting on a deduction.
Body Oil for a Professional Bodybuilder – “Flex, File, Deduct”
One competitive bodybuilder managed to convince the IRS that baby oil and tanning lotion were essential business expenses—because “shiny muscles make more money.”
✅ Approved! If your job requires you to glisten like a Greek god, oil is now officially a necessity.
Cat Food for a Business Expense – “The Meow Right-Off”
A junkyard owner deducted cat food as a legitimate business expense because the feral cats he fed helped control the rat problem. The tax court ruled that if cats are working employees, they need to be fed.
✅ Approved! Meanwhile, actual employees still don’t get free lunch.
Clarinet Lessons as a Medical Deduction – “Beethoven’s Tax Loophole”
One couple successfully deducted clarinet lessons for their child as a medical expense because playing the clarinet helped correct the child’s overbite.
✅ Approved! So next time you’re debating between braces or music lessons—just buy a tuba.
Whaling Boat Repairs – “Moby-Deduction”
Believe it or not, there was once a tax break specifically for whaling captains to deduct the cost of their whaling boats. This lasted until 2004, when lawmakers finally realized “Hey, maybe let’s not reward whale hunting?”
🚫 Denied! Sorry, Captain Ahab, the IRS is no longer subsidizing your quest for revenge.
A Swimming Pool for Medical Reasons – “The Backyard Spa Deduction”
One taxpayer deducted his backyard swimming pool as a medical necessity because his doctor prescribed water therapy for arthritis. The IRS ruled that it was legit—as long as he only used it for medical purposes.
✅ Approved! So next time you throw a pool party, just tell the IRS it’s “physical therapy.”
Beer for Business – “Booze and Write-Offs”
A gas station owner successfully deducted free beer given to customers as a marketing expense because it encouraged them to buy more gas.
✅ Approved! Meanwhile, millions of business owners are now reconsidering their customer service strategy.
Breast Implants as a Business Expense – “IRS-Approved Augmentation”
A stripper successfully argued that her breast implants were a business expense because they directly increased her earnings. The tax court ruled that they were a necessary business enhancement and allowed the deduction.
✅ Approved! Somewhere, plastic surgeons are revising their invoices as “business investment opportunities.”
A $75,000 Ostrich – “Feathered Financial Planning”
One Texas rancher deducted a $75,000 ostrich as a business expense because he claimed it was for breeding purposes. The IRS didn’t believe him—until he proved that his ostrich farm was a legitimate operation.
✅ Approved! If you’ve ever wanted a giant bird but couldn’t justify the cost, now you have an excuse.
A Fake Kid – “Phantom Taxpayer”
A taxpayer once tried to claim a dependent that didn’t actually exist—a completely fake child. The IRS eventually caught on, but he got away with it for a few years before being caught.
🚫 Denied! Sorry, imaginary children are not tax-deductible.
Final Thoughts: The IRS Tax Game Is Rigged… But In Hilarious Ways
While the rest of us are panicking over whether we can write off a home office or not, some people are literally deducting their pets, pools, and body enhancements.
So, next time you’re doing your taxes, just remember: if someone can deduct an ostrich and a stripper can write off implants, your home office expenses are probably just fine.
Now, if you’ll excuse me, I need to go register my cat as a “Business Pest Control Specialist” and claim back all his meals.
Happy filing!
