Happy Friday.
People get very creative during tax season.
After years of working in taxes, I can confidently say there are two things you should never underestimate:
- The complexity of the tax code
- Humanity’s confidence in calling random things “business expenses.”
Some deductions are perfectly legitimate. Others make IRS auditors quietly stare into the distance while reconsidering their career choices.
Here are a few real examples of unusual deductions people actually tried to claim.
The “Pimped Out” Amish Buggy
An Amish businessman attempted to deduct his buggy as a business expense. But the accountant became suspicious after noticing the upgrades:
Velvet interior.
Hydraulic brakes.
Tinted windows.
A speedometer.
At some point, the buggy stopped looking like transportation and started looking like a 1998 limousine. The IRS allowed some business use but disallowed many of the luxury upgrades. Apparently, even horse-and-buggy travel has limits on what counts as “ordinary and necessary.”
The “Freakishly Large” Business Asset
In one of the most famous unusual tax cases ever, exotic dancer Chesty Love successfully deducted her breast augmentation surgery as a business expense.
Why?
Because the court ruled the implants were so unusually large that they were used strictly as part of her performance and created personal hardship outside of work. In tax court language, they were considered a “business prop.” Somewhere an IRS auditor definitely had to pause and rethink their life choices while writing that decision.
The IRS-Approved Body Oil
A professional bodybuilder successfully deducted body oil used during competitions because it enhanced muscle definition under stage lighting. But when he tried deducting buffalo meat and specialty vitamins, the IRS said no. Apparently there is a line between “professional competition expense” and “you just really like protein.”
The Cat Employee
One junkyard owner successfully deducted cat food because the cats worked full-time controlling rats and pests around the property. Meanwhile, another taxpayer unsuccessfully attempted to deduct expenses for a pet goldfish as an emotional support animal. The IRS was apparently unwilling to recognize emotional support goldfish as a qualifying business expense.
The Musical Overbite
Back in 1962, the IRS allowed parents to deduct the cost of a clarinet and music lessons as a medical expense.
Why?
An orthodontist recommended playing the clarinet to help correct the child’s severe overbite. Which means somewhere in America there was a kid practicing scales while unknowingly participating in one of the strangest tax deductions in history.
The Pizza Delivery Luxury Car
One taxpayer claimed a luxury vehicle was necessary to maintain a professional image as a pizza delivery driver. The IRS auditor decided to investigate further. Turns out the pizza company delivered entirely by bicycle. That deduction crashed faster than a teenager learning stick shift.
The Tax-Deductible Arsonist
And finally…
In perhaps the boldest example of “creative accounting,” one struggling business owner attempted to deduct money paid to an arsonist hired to burn down the business. The payment was labeled as a “consulting fee.” That deduction was denied immediately, which probably surprised absolutely no one except maybe the taxpayer.
Many people genuinely don’t understand what qualifies as a legitimate tax deduction. They hear phrases like “write it off” and assume almost anything connected to work automatically counts. Unfortunately, the IRS has very specific rules about what is considered ordinary, necessary, and properly documented. And when taxpayers get too creative, things can go sideways quickly.
That’s often when people end up receiving IRS notices, audit letters, or questions they never expected.
And if you ever find yourself wondering whether something is deductible, it’s probably a good idea to ask before claiming your emotional support goldfish. Because not every “business expense” survives an IRS audit.
Now I’m curious…
What’s the funniest or strangest deduction you’ve ever heard someone try to claim?
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