Bankrate.com recently shared their 10 craziest tax write-offs. I picked my favorite 5 and share them below. Some of them are really just failed write-off attempts but they’re all pretty funny.
1. It Went Up in Smoke
A drug dealer, facing prison time, didn’t want to serve more time for tax fraud. Therefore, he shared his dealer income with his CPA and paid the taxes on it. He then wanted to deduct some of his expenses. But, no deductions are allowed since it’s an illegal activity. The CPA said “let’s just say he wasn’t getting 1099s from his customers. He gave me a number and we paid taxes on it. I had no basis for it because he dealt in cash.”
2. Silence is Golden … and Deductible
A man in Texas was tired of his noisy neighbor so he bought the house from him, ripped it out of the ground, and donated it to a local women’s shelter. He was actually allowed to deduct some of the value of the house as a charitable contribution.
3. The ‘Zoolander’ Deduction
Apparently the Derek Zoolander types, and others in front of the camera, often try and deduct personal property and perks like wardrobes and wax jobs. Says one CPA who handles a lot of clients who are models, “models can deduct a lot of makeup and certain pieces of apparel, but it has to fit the rules. We don’t let them deduct the pedicures, manicures and back waxing for therapeutic reasons.”
4. The $50,000 “Business” Meeting
A lawyer with 300k in business income listed a $50,000 entertainment expense for one party as a tax deduction. The man said it was for his clients, but later admitted that it was his daughter’s wedding which several of his clients had been invited. Expensive: yes. Deductible: no.
5. Inflating your Assets
Lastly, the craziest and most successful deduction came from a topless dancer who “got breast implants and wrote them off as a business deduction…and was able to deduct them.” The IRS challenged the whole thing. However, she apparently went to court and won.