20 amazing, outrageous and just plain weird tax deductions


Well, it's that time again. The tax deadline is just around the corner. If you're like me, you will have taken care of your taxes months ago and already be enjoying the cash your high-interest savings account is giving you on your return.

If you're smarter than me, you won't have any tax return at all. It's best to come out owing nothing and getting nothing. Evens is best here. But if you still haven't done your return, take a look at the top 20 funky, strange and outrageous deductions that folks have tried, and sometimes failed, to get away with.

It's ironic that I was sweating over the deduction of office supplies for my home business, when some folks out there are deducting breast implants and beer. As I'm often told, God Bless America.

1 - Free beer - YES
Strange but true. A gas station owner gave his customers free beer (brand unknown…I doubt it was Stella Artois though) in lieu of trading stamps. And the Tax Courts said yes, this is a legitimate business expense and tax deductible. Which makes the next entry even stranger…

2 - Free whisky – NO
How ironic. A cunning fella thought a case or two of whisky would make nice client gifts, and thus tried to deduct them on his annual tax return. The category he chose was client entertainment. However, not only was it not allowed, it was a gift that violated state laws. Ouch.

3 - Cost of hiring an arsonist – NO
Hard to believe, right? A man with a failing furniture business decided to hire someone to burn it down. The store-owner's plan was not only to collect the $500,000 insurance money, but also to deduct the $10,000 expenses of hiring the arsonist! He was denied. I’m sure it wasn’t too long before the police were also looking carefully at his return. Not a smart man.

4 - Fake Boobs - YES
This one is infamous. A stripper going by the name of CHESTY LOVE used her hard-earned savings to boost the size of her boobs, to the eye-popping size of 56-FF (do they even make bras in that size?) She figured it would get her more tips. And the write-off was allowed, being considered a stage prop essential to her act. Ha!

5 - Prostitution expenses – NO
Maybe in Amsterdam or at the Bunny Ranch in Nevada, but you can’t deduct expenses of illegal professions. Trying to deduct 4000 condoms or push-up bras are no good if you put down “prostitute” as your career. Similarly, drug dealers can’t deduct the cost of baggies or soil for Marijuana plants.

6 - Cat food - YES
Junkyard owners set out bowls of pet food nightly to attract wild cats. The wild cats also took care of their nasty snake and rat problem, making the junkyard safer for customers and providing a useful business service. Yep, you guessed it…the pet food is a business expense, it was allowed. I need to get the number of their tax attorney.

7 -Your own racehorse – NO
I can see how this would be a business expense to some people. But if you just go out and buy your own prize-winning horse, name it after yourself (the ego on some folks) and then take clients out to see your horse run, you cannot deduct this. It’s not a business expense, it’s a personal expense. But hey, if you can afford a racehorse and stables, why are you worried about the deduction in the first place?

8 - A fabulous African Safari - YES
If the IRS considers a business trip "ordinary and necessary", you can take it as a deduction. For the owners of a dairy business, this included a wonderful African Safari, because many of the activities on the trip were focused on wild animals. Please note – going to see adult shows in Vegas would not count as viewing exotic wildlife.

9 - The costs of moving…the family pet - YES
Whether you’ve got a Great Dane or a Great White Shark, your pet is considered a personal effect. And that’s great news for you. When it comes to any expenses relating to any kind move associated with a job, the tax man says yes. But I suspect hiring a Hummer Limo to move your gerbil across the state may not be looked upon favorably.

10 - A Trip to Bermuda – YES, YES, YES
I love this one. I have to find a way to do it. ANY business convention held in Bermuda can be written off without even showing there was a special reason to hold your business meeting in paradise. And it’s not the only place. Barbados, Costa Rica, Dominica, the Dominican Republic, Grenada, Guyana, Honduras, Jamaica, Saint Lucia, Trinidad and Tobago, Canada, Mexico and all U.S. possessions also fall into this special tax treatment. But outside the U.S. is a different story. I guess I can’t hold a board meeting in England so I can go see my folks then :-(

11 - Body Oil - YES
If you’re a regular Joe, body oil is a once in a blue-moon splurge. Maybe something to spice up an evening with your partner, but certainly not a write-off. However, if you’re a pro bodybuilder and need gallons of body oil to make your muscles glisten, then it is a genuine tax write-off. Just don’t turn up at a client meeting covered in oil, wearing nothing but a thong and a smile. It won’t be considered “ordinary and necessary.”

12 - A trip to the Super bowl – NO
I’d like to put this one in the ‘nice try’ category. Someone decided to take clients and their spouses to the Super bowl, but just could not prove that the shindig was in any way related to business. And even if it was, it’s an extravagant expense for a meeting and would have been disallowed anyway. Sorry bud.

13 - A Private Airplane - YES
A couple with a rental condo didn’t fancy the hassle of driving up to 7 hours to check on it. They didn’t want to be stuck to the schedule of the only daily flight available. So, they did what you ore I would do. They bought their own jet! They were allowed to deduct all expenses on the jet relating to the condo, including the high costs of fuel. That must have been some

14 - A Mink Coat - NO
And thank goodness, because I hate fur. Claiming that the Mink coat was a conversation piece when visiting clients with his wife (what was the topic…blood on the runway?) a man tried to deduct the garment. Fortunately, he was denied.

15 - Babysitting costs - YES
Believe it or not, you can deduct the cost of a babysitter as a charitable deduction, if the mother of the child is leaving the house to do volunteer work for a charity. Which, of course, we all do on a daily basis.

16 - A ‘Playmate' Party - YES!
How he got away with this one is beyond me. The owner of a nightclub promotions firm decided that a regular party wasn’t good enough for his clients. So, he brought in a bunch of scantily clad “bunnies” as decoration. The tax man said sure, it’s a valid expense. Whether or not pictures of the bunnies were attached to the return is unknown at this time.

17 - A Nuclear Fallout Shelter – NO
This one bombed (ouch, sorry…bad pun). Yup, way back in the days of the cold war and the threat of nuclear meltdown, one clever chap built a nuclear fallout shelter on his property and then decided to list it as “preventative medicine.” The IRS gave that one a big thumbs down. But who’ll be laughing if Word War 3 does happen?

18 - A beautiful swimming pool - YES
This one’s a great example of lateral thinking. After being told by his doctor that he needed to exercise (after developing emphysema), the smart fella put in a swimming pool. The deduction was put down as a necessary MEDICAL EXPENSE and was allowed, along with the various chemicals, heating, cleaning and general upkeep of the pool. Now that’s using your head.

19 - Dancing lessons – NO
Dancing With The Stars may be popular, but it’s not going down well with the IRS as the subject of a deduction. You CANNOT take dancing as a deduction for medical expenses, and the following reason are outlawed – dancing to relive varicose veins, dancing to cure arthritis and finally, dancing to alleviate nervous disorders. Try any of these and you’ll be dancing all the way to the tax courts.

20 – Sperm donation as a loss – NO
It’s one thing to make a little extra cash as a sperm donor. It’s quite another to try and claim a depletion loss on the aforementioned sperm. Unless you’re an oil well, that kind of depletion is not really going to make much of an impact.


Disclaimer: The links and mentions on this site may be affiliate links. But they do not affect the actual opinions and recommendations of the authors.

Wise Bread is a participant in the Amazon Services LLC Associates Program, an affiliate advertising program designed to provide a means for sites to earn advertising fees by advertising and linking to amazon.com.

Will Chen's picture

Sounds like a plan Paul.

Andrea Karim's picture

I'm wondering if the Playboy Bunnies as honored guests at Wise Bread Con would be a frugal decision or not, in terms of ROI?

Also, I think I might change my nom de blog to Chesty Love. "Opinionated Love" and "Snarky Love" don't have the same ring.

Bless you, Paul, for objecting to fur. Topical! I was just writing up a post about it.

Andrea Karim's picture

I thought a big bell flew in from Rome?

Guest's picture

Right, I can see how viewing those wild dairy cows on safari in Africa would be a tax deduction.

Will Chen's picture

"I thought a big bell flew in from Rome?"

A bell, thats.... oh well, you know.  =) 

"Right, I can see how viewing those wild dairy cows on safari in Africa would be a tax deduction."

Happy cows make happy steaks. 

Guest's picture

How come dance lessons won't be deducted? What if you need to learn how to dance in order to teach one of your clients so that he can test your dancing shoes?



Guest's picture

I agree.. some of these are ridiculous! I am a professional tarot reader (no bashing please, it's a service industry, I enjoy my job and I'm paid well for what I do.. it's not for everyone).

Anyway, I have a solid client base. I am able to write off the supplies for my hands and fingernails. No, I do not have those wicked long false nails.. I have natural, normal length nails. I have to keep my hands looking nice for my job. I have to also buy anti-viral hand sanitizer to use between clients. They handle my cards. Some people come in with colds/flu and have no idea that they put myself and my family at risk by exposing me to germs. If I get sick, I cannot perform my job properly.

It was a great day when my tax preparer informed me of the write offs. It gets expensive. I was then able to gauge how much I was spending on supplies and modify DOWN accordingly. To me, if you get a break like that, you should really keep track and be thankful; rather than spending UP. Personally, I like to save money here and now.. not at the end of tax season (but I am not complaining about that either).

Thanks for the article! Nice job!

Guest's picture

Can you credit your sources ... Kiplinger's had this list of allowed tax deductions researched from tax court case files for several years ... The Dolan's flagges a lot of your disallowed tax deductions.

Where did you do your research?

Guest's picture

Sorry you cannot deduct babysitting while doing charity work. Please see IRS Publication 526

"No, you cannot deduct payments for child care expenses as a
qualified organization. Even if they are necessary so you can do
volunteer work for a qualified organization."


Guest's picture

Even though that statement appeared in the document it followed the statement "If you do volunteer work for a qualified organization, the following questions and answers may apply to you." The specific details of the case above were not disclosed, so it could have been treated differently the the case addressed in the question and answer section.

/** Fix admin settings safe to ignore showing on unauthenticated user **/