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

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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

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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

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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

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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

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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

Related posts:

  1. Don’t Forget These 10 Tax Deductions
  2. Pay Your Property Taxes and Sales Taxes Prior to Year End
  3. Black Friday is Here – This is Crazy!
  4. Tuesday Tax Tip: Tax Prep Checklist

11 Responses to 5 Crazy Tax Write-Offs
  1. courtney
    March 24, 2008 | 1:23 pm

    Back waxing for “therapeutic” reasons????

  2. teresa
    March 24, 2008 | 4:13 pm

    Orange-Mocha-frappuccino!!

  3. Andy
    March 24, 2008 | 9:23 pm

    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. Four Pillars
    March 24, 2008 | 9:27 pm

    I think that last one is perfectly legit… :)

    Mike

  5. Nivek
    March 25, 2008 | 5:49 pm

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

  6. Jayle
    March 25, 2008 | 8:19 pm

    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
    April 7, 2008 | 1:01 am

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

  8. Sanjay
    June 1, 2009 | 7:06 pm

    Does that mean I can get a penis enlargement and a liposuction if I were a male porn star? More reasons to consider a temporary career change!

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