8 of the most insane tax loopholes you probably didn’t know about


Tax time is here again, and that means that everyone is busy looking for ways to keep Uncle Sam from getting his grubby little hands all over their hard earned money. Naturally, this means that people tend to become, um, creative when it comes to some of their deductions. Most of these are doomed to failure – just because your cousin’s roommate’s uncle’s cellmate named Earl the Accountant said it’s cool doesn’t mean you still shouldn’t run that shit by a licensed CPA – but there are some legitimate tax loopholes that actually work even though they might sound ridiculous. And because we care about you and your financial well-being, we thought we’d help you out by letting you in on these, 8 of the most insane tax loopholes of them all.

8. Claiming Kidnapped Kids

Good news! If your kids get snatched, you can still claim them as dependents until their 18th birthday. You used to be able to claim them only the year that they were, uh, napped, but now you can just flat out lie to the government and say they still need you even though the only thing you’re providing them with are tears and prayers, which, sadly, are not tax deductible. But kids are, and I guess this is the government’s way of making it up to you since the police forces and federal investigators your tax dollars fund failed to find your kids. Call it a tax refund, I guess.

7. Pet Food

Slow down, you can’t just write off all those bags of Purina Cat Chow you’ve picked up throughout the year. Not unless you can prove that your pet is integral to your business, that is. Think guard dogs, that sort of thing. If you can prove that your pet is a legit business expense then you can write off just about anything. That’s why, once a month, I let a chimpanzee write my articles. I get the tax breaks and he gets a creative outlet beyond smearing his own poop on the walls. Everybody wins.

6. Renting Cows

In Florida there has long been a law on the books taxing farmland at a lower rate than other land. You don’t even have to turn a profit on your “farm,” you just have to prove that you’re trying to run one, no matter how shitty. In fact, all it takes to apparently prove to the government that you’re a legit farm is to rent a few cows and let them hang around for a little while, maybe take a few pictures, and, I don’t know, wait for one of them to poop or something so you can mail it to the feds. Believe it or not, companies like Disney have saved over $1 million in taxes via this loophole, which means that, yes, the government of the most powerful country on earth is routinely outsmarted by Goofy.

5. Caribbean Vacations


This doesn’t work for all countries, but there are several island nations in the Caribbean which you can visit and then claim as a “business” expense as long you make minimal effort to show that you had to attend a convention there. So, basically, just look for something, anything really, related to your line of work in Jamaica or Bermuda or several other countries, head down there, pop into the convention for ten minutes and then tell the government that you had no choice. Sure, the only thing you’ll be learning while you’re there is how to do tequila shots from between an island girl’s boobs, but you never know when that will come in handy around the office.

4. Rolling Your Own Cigarettes

In Washington state, unrolled tobacco is taxed at a much lower rate than rolled cigarettes, so a lot of stores there have started to sell loose tobacco to customers and then let them roll their own cigarettes at rolling stations they have set up complete with rolling machines. Sure, you’ll still die of some hideous lung disease and your mouth will taste like the inside of a bum’s ass, but think of those tens of dollars you’ll be saving every year! Plus, you’ll look cool.

3. Deducting Your Taxes

Wait… what? Yeah, you can deduct what you pay in taxes. Or at least certain types, anyway. You can actually federally deduct either what you pay in state sales tax or in state income tax, whichever is higher. Further, if you’re self-employed, you can deduct half of your social security contribution. That’s because companies and employees are required to each pay half of the social security deducted from your paycheck. Basically, your company matches your contribution. If you work for yourself, though, you’re stuck paying the whole share. Bummer. But, the government will let you at least deduct the half that your employer would normally pay, so… yay? It’s complicated, so ask your accountant, unless you’re comfortable telling the government that Neil from Guyism said it was cool. I’ll totally back you. Maybe.

2. Not Having Any Arms or Legs

This one just strikes me as really funny. It’s not the loophole itself – an Oregon law which allows you to claim a deduction if you’re missing any limbs – but the amount you get: $50. I mean, why bother? I have some questions, though. Do you get $50 total? Or is it $50 per limb? Because I can see how that could add up. I’m just saying, if you’re desperate for some cash, there are a lot of things that can probably be technically considered “limbs,” right? I mean, could a toe or a finger be considered a limb? That’s $1,000 right there! Could you get away with claiming your fingernails as limbs? Think it over, or at least ask the right questions, and maybe save your nail clippings. Of course, you’d have to move to Oregon, but Portland’s kind of a hipster city, and I think no one would even blink if you just had a friend wheel your limbless torso around town in a wheelbarrow. I’m just trying to help.

1. Fake Boobs


I bet this one was passed during the Clinton administration. No, but really, this is no different than pet food, in that it flies only as long as you can prove that it’s a legitimate business expense. So, ladies, I’m not saying you should start stripping, but…

Okay, maybe it’s not that simple – after all, as the years go by, you have to start accounting for depreciation and I’m not sure quite how you’d figure that one out, especially in stripper years, which I’m pretty sure involves some sort of advanced calculus – but I just respect you as businesswomen, and want to see you maximize your assets. Just remember, the bigger the rack, the more you get back. I’m pretty sure that’s in the Constitution.

Tax forms image by Shutterstock
Vacation image by Shutterstock
Breast implants image by Shutterstock