5 Crazy Tax Write-Offs

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.

Photos: by kk+, foto3116, No Middle Name , ulalume

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Last Edited: February 17, 2012 @ 6:30 pmThe content of ptmoney.com is for general information purposes only and does not constitute professional advice. Visitors to ptmoney.com should not act upon the content or information without first seeking appropriate professional advice. In accordance with the latest FTC guidelines, we declare that we have a financial relationship with every company mentioned on this site.
About Philip Taylor

Philip Taylor, aka "PT", is a CPA, financial writer, podcaster, FinCon Founder, husband, and father of three. He created PT Money back in 2007 to share his thoughts on money and to meet others passionate about managing their finances. All the content on this blog is original, and created or edited by PT. Read more about Philip Taylor, and be sure to connect with him on Twitter, Facebook, or Google+. Listen to the new podcast, Masters of Money!


  1. Back waxing for “therapeutic” reasons????

  2. Orange-Mocha-frappuccino!!

  3. Too funny…wish I had thought of some of these “deductions” when I was doing my taxes and got hit with a bill.

    Great blog and I will be subscribing.

  4. I think that last one is perfectly legit… 🙂


  5. I obviously need to get more creative with my tax write-offs!

    • Muy divertido … Ojalá hubiera pensado en algunos de estos “descuentos” cuando yo estaba haciendo mis impuestos, y fue golpeado con un proyecto de ley. Gran blog y voy a suscribir.http://www.agame.fm

  6. I see no problem with a stripper deducting her boob job expenses. It’s a legitimate business, fueled by tips. Her gross receipts definitely improve, which leads to a higher income. (and more taxes for the IRS!)

    My question is this:

    What weird deductions do IRS tax agents claim? Or do they pay taxes at all?

  7. All About The Ben says:

    I had a friend ask me if he could deduct hair cuts because he needed a good hair cut for an office job.

  8. As Jayle says, there are many tax deductions that are allowed especialy for business reasons. Example #5 may sound crazy but what if the young lady was a toppless dancer and she needed “bigger melons” to make more in tips, this is probably why she won in court.

    Example #4 the $50,000.00 wedding expense should have been flagged by his accountant right away. The tax department will question a $50,000 entertainment expense because it makes up 16% of this persons total income. Keep your entertainment expenses below 5% and the tax guys propbably will not ask any questions.

    Think about what you claim, if you trigger a tax audit the few thousand that you thought you were saving may end up creating a nightmare of financial problems.

  9. If I work in higher education doing high level outreach to business owners, community members alongside assisting students in a professional role, can I deduct my wardrobe and makeup expenses as it directly relates to my professional appearance in this position?

  10. I don’t think so. Ask your CPA to be sure though.