As the year comes to a close and you're bleary-eyed from present-buying and year-end tax planning, we thought we'd lighten the mood a bit. While you may not think there's much to laugh about when it comes to taxes, you might just be surprised.

We all know about the good old standard tax deductions like write-offs for charitable donations and home offices. And thousands of Americans are taking advantage of the new tax credit that Congress just extended for first-time home buyers. But there are a few breaks that you might not realize the IRS is willing to stamp "approved" that could save you money on your tax bill. And if you can't claim them on your forms this year at least you can benefit from a little laughter.

Hiring Help
Okay, not just any help. But if you need to pay for child care because you are donating time to a nonprofit organization or you are doing charitable work you can deduct that fee from your 1040 form. That's right - if you pay someone to babysit because you're working for someone for no pay, you can write it off. Admirable to be sure, but it seems like a long way to go around the bend to save a little on your tax bill.

Medically-Necessary Massages
Since this deduction was originally written into the tax code in 1962, accountants and tax lawyers have made sure their clients are keeping all their doctor's notes. The rule states that anything that your doctor prescribes as "medically necessary" can be deducted from your taxes.

That means that if your doctor tells you to get therapeutic massages you can keep the receipts and knock that expense off as deductible. The same goes for aqua therapy (backyard pool installation and maintenance anyone?) and restrictive diets (make that call to Jenny Craig).

However be aware that the IRS combs through medical deductions very carefully so don't try to get creative or it could end up costing you much, much more. (If the IRS finds errors, it will cost you. Find out how to fix them - and prevent them in the first place in Inaccurate Tax Return, Now What?)

FedExing Fido
Okay, so FedEx won't really overnight your family's pooch - but you can deduct the expenses associated with moving any of your personal effects due to a job-related relocation. And, as a personal effect, your favorite animal's transportation can be written off your personal taxes.

Attorney Fees for Illegal Activity
Wait, what?! It's true. While you are required to pay taxes on any income earned through illegal activity such as theft, bribery or drug-dealing, if you are unfortunate enough to get caught, the good news is you can write off the cost of hiring an attorney to defend you during your trial.

To Ride the Wind
Concerned about the environment? Not worried about what your neighbors think? Consider installing a wind energy system and you could get a tax write-off. Put up one of those attractive wind turbines that dot the plains and Uncle Sam will repay your environmental kindness with a nice little break on your tax return.

Houseboat Ahoy!
Most of us know that you can deduct the interest you pay on your mortgage but we typically tend to envision a neat single-family home surrounded by a white picket fence. However if you got a loan to finance a houseboat that you call home (provided it has sleeping, cooking and "toilet facilities"), you can write that interest expense off as well. I wonder if the Captain, Gilligan and his crew split the write-off?

Business Breaks
If you are a small business owner the list of potential tax breaks can sound just downright strange. Anything that is can be demonstrated to be a legitimate "ordinary and necessary" business expense can be deducted. So that means you might be able to deduct the following. (Running your own business has both personal and financial perks. Find out more in 10 Tax Benefits For The Self-Employed.)

  • Jetting Off to Jamaica
    If you decide to reward your employees with a company retreat in Bob Marley's home country, or to plan your company's next strategy meeting in sunny Barbados the tax man will allow you to write it off. In fact any business meetings held in some of the most beautiful places in this hemisphere including Barbados, Costa Rica, Dominica, the Dominican Republic, Grenada, Guyana, Honduras, Jamaica, Saint Lucia and Trinidad and Tobago - not to mention Canada, Mexico and any U.S. state or territory - can be claimed as a legitimate, and deductible, expense.

  • Captain Ahab would Approve
    To help Native American Eskimos in his home state preserve their cultural heritage and custom of whale-hunting, former Senator Ted Stevens was able to insert a $10,000 deduction for qualified whale-hunting expenses in the American Jobs Creation Act of 2004. So if you're a whaling captain recognized by the Alaska Eskimo Whaling Commission you can write off money that you shell out for whale-related work expenses like repairing your boat or buying food for your crew.

  • Shipping Sheep
    If you are a farmer and you need to pay for sheep - or any other qualified form of livestock including "fur-bearing animals" - to be shipped to your ranch, you can write if off on your taxes. For that kind of delivery, you should plan on tipping your mailman well.

The Bottom Line
While taxes might not seem like a very funny topic, hopefully some of these available deductions tickled your funny bone. At the very least, you or someone you know might benefit from one of these odd write-offs. (The receipts you cram into your wallet could be replaced with cash come tax season. Find out how you could save in 10 Most Overlooked Tax Deductions.)

Related Articles
  1. Stock Analysis

    The Best Stocks to Buy for Less than $10 before Year End

    Learn about the best stocks to buy under $10. These stocks are speculative but have considerable upside given their valuation and market conditions.
  2. Investing Basics

    10 Companies That Yuppies Love

    Learn about 10 companies loved by the modern Yuppie, including how this demographic's impressive buying power has boosted these companies' earnings.
  3. Taxes

    What's Wrong with the American Tax System

    American's are highly taxed and we still run a deficit. We explain why.
  4. Professionals

    Advisors: Warn Clients About These Audit Triggers

    There are several factors that may increase the risk of an audit, especially with high-net-worth clients.
  5. Retirement

    Top Tips for Minimizing Taxes on Social Security

    Social Security benefits are taxable under certain circumstances. Here are some ways retirees can lessen the tax burden.
  6. Professionals

    Retirement Plan Options for Small-Business Owners

    Small-business owners and self-employed individuals are responsible for funding their own retirement. The SEP-IRA and solo 401(k) are tools to consider.
  7. Taxes

    Employers: Don't Forget IRS Form 941

    Your obligations as an employer include various employment taxes. Use this form to report them.
  8. Entrepreneurship

    What's the Purpose of IRS Form 1065?

    Business partners need the information on this form to complete their own tax returns. Here are the details.
  9. Taxes

    20 Medical Expenses You Didn't Know You Could Deduct

    To lower your tax bill, be sure not to miss out on these commonly overlooked medical tax deductions.
  10. Retirement

    How IRS Form 5498 Helps You

    If you have an IRA, you'll be getting this form. Here's the useful information it contains.
RELATED TERMS
  1. Duty Free

    Goods that international travelers can purchase without paying ...
  2. Negative Option Deals

    A dubious business practice that involves supplying a typically ...
  3. G.19 Report

    A monthly statistical report from the U.S. Federal Reserve that ...
  4. Drip Pricing

    A pricing technique in which only part of a product or service’s ...
  5. Tax Deductible Interest

    A borrowing expense that a taxpayer can claim on a federal or ...
  6. Behavioral Modeling

    Using available and relevant consumer and business spending data ...
RELATED FAQS
  1. Are spousal Social Security benefits taxable?

    Your spousal Social Security benefits may be taxable, depending on your total household income for the year. About one-third ... Read Full Answer >>
  2. How do you calculate penalties on an IRA or Roth IRA early withdrawal?

    With a few exceptions, early withdrawals from traditional or Roth IRAs generally incur a tax penalty equal to 10% of the ... Read Full Answer >>
  3. Are credit card rewards taxable?

    Credit card rewards are taxable in the United States some of the time. The Internal Revenue Service (IRS) classifies credit ... Read Full Answer >>
  4. Are Social Security payments included in the US GDP calculation?

    Social Security payments are not included in the U.S. definition of the gross domestic product (GDP). Transfer Payments For ... Read Full Answer >>
  5. Are Social Security benefits taxable after age 62?

    Eligibility to collect Social Security benefits begins at age 62. Many seniors, to collect larger benefit amounts, wait until ... Read Full Answer >>
  6. What are the best free online calculators for calculating my taxable income?

    Free online calculators for determining your taxable income are located at Bankrate.com, TaxACT.com and Moneychimp.com. Determining ... Read Full Answer >>

You May Also Like

Trading Center
×

You are using adblocking software

Want access to all of Investopedia? Add us to your “whitelist”
so you'll never miss a feature!