CHICAGO - NOVEMBER 1: Current federal tax forms are distributed at the offices of the Internal Revenue Service November 1, 2005 in Chicago, Illinois. A presidential panel today recommended a complete overhaul of virtually every tax law for individuals and businesses. (Photo Illustration by Scott Olson/Getty Images)

Can I deduct this from my taxes? I always ask myself. I’m sure this thought has crossed your mind too since money is tight for many of us.

Many taxpayers have come up with a lot of zany arguments to justify their federal tax breaks. To enjoy some laughs before the 2022 tax season, here are 15 of the most creative ones that the courts decided weren’t quite successful thanks to Kiplinger’s help. Check out these 15 ridiculous things people tried to deduct on their taxes below. If you would like to see why these taxpayers’ arguments didn’t fly in court, click here.
  • 1. Investigating Daddy's Mysterious Death

    This one is wild. A CPA paid millions of dollars to private investigators and other experts to help him find out whether his father, who died when the taxpayer was a child, was murdered or committed suicide. According to Kiplinger, he believed that if he gathered enough evidence, the story could become a book or even a movie. The Tax Court categorized his activity as a hobby and nixed the write-off.

    Tombstone

  • 2. Relaxation

    Someone thought that they could use relaxing as a tax deduction. Why? Because the clients were harassing her so she occasionally booked a hotel room to relax in. On her return, she deducted the cost of this rest as a business expense.

    Pillows and a Bed

  • 3. The Idea of a Novel

    Yeah, the idea of having a book doesn’t cut it as a tax break.

    Book

  • 4. A Horse That Didn't Exist

    So this woman thought she could claim a horse breeding business…that she didn’t start yet. The IRS said no-no because well, she didn’t own any horses.

    Horse Feild

    (Photo by Mark Evans/Getty Images)

  • 5. Pageants Are Not A Tax Write-Off

    A little girl was a pageant queen and he parents tried to bank on this. She won between $1,000 and $2,000 in prize money each year that was deposited into her college savings account. The parents reported the income on their returns and also took large write-offs for the cost of travel, costumes, and other expenses.

    Beauty Pageant

  • 6. Pizza for the Children

    In Washington, D.C., a woman operated staffing and consulting business. Her three children, ranging in age from 8 to 15, helped her with tasks like shredding, stuffing envelopes, copying, and tending to the yard around her home office. Instead of paying cash, she bought her children meals, including pizza, and paid for tutoring. Tax Court rejected her claim to deduct the kids’ “wages” as business expenses.

    Pizza

  • 7. A Love Affair

    Upon discovering that his wife had an affair with her doctor, a police officer confronted the doctor and threatened legal action. The doctor eventually agreed to pay $25,000 to settle the case. According to the Tax Court, the payment of $25,000 was taxable as income because it was offered as a settlement for the doctor’s misconduct.

    Love

  • 8. Prostitutes and Porn

    In a year, a tax lawyer spent more than $65,000 on prostitutes and pornographic materials. Making a novel argument, he claimed that sexual therapy had positive health effects. The Tax Court red-lighted his write-off, saying that his conduct not only was illegal but also wasn’t for the treatment of a medical condition.

    Pole Dancer Legs

  • 9. Killer Taxes for Mom

    A wife was jailed for killing her husband. Although she was named as the primary beneficiary of his 401(k) plan, state law barred her from receiving any of the funds because of her crime. Therefore, their son was named the secondary beneficiary of the account. He claimed that his mother should be taxed on the payout as the intended beneficiary. An appeals court gave him an A for effort but an F in taxation, ruling that he owes tax on the distribution.

    Jail

  • 10. Lunch for Free? Nope!

    During lunchtime, a law firm partner discussed his practice’s business with his colleagues. Nevertheless, Uncle Sam balked at his request to pick up a portion of the tab. The Tax Court sided with the IRS, ruling that the cost of the meals was a non-deductible personal expense despite the fact that business was discussed. While the partner can have his cake and eat it too, he can’t receive a subsidy from other taxpayers for his meals.

    Photo by Robin Stickel from Pexels

  • 11. A Fish Tank

    Tax returns for a couple were filed late and had many questionable deductions, such as furniture and a fish tank. The accountant had been sent to jail for killing her husband, and the person who took over the office was incompetent, so their late filing should be excused. But they were turned down by the Tax Court.

    Fish Tank

  • 12. Credit Card Points

    Tax Court tested this proposition, in a case where an individual manipulated American Express’s rewards program and racked up the points. With his credit card, he purchased VISA gift cards, earned cash rewards for the purchases, then used the gift cards to purchase money orders that he deposited into his bank account. He also bought reloadable debit cards and money orders directly with his credit cards. Over a two-year period, he spent $6 million on these purchases and earned $300,000 in rewards. According to the Tax Court, the rewards earned through the purchase of the VISA gift cards are tax-free. But rewards earned on the direct purchase of money orders and reloadable debit cards are taxable.

    Credit Cards

  • 13. Dead Animal Collection

    Claiming a $1.43 million write-off for animal hides, skulls, horns and other hunting specimens he donated to charity is how a big-game hunter found himself in the crosshairs of the IRS. It was a no-go for this taxpayer.

    Animals

  • 14. Burning Down Your House

    Homeowners who want to tear down their homes and rebuild sometimes ask firefighters to burn them down. This training exercise serves the public good. But to get a deduction, an Appeals Court said that the homeowner must show that the value of the donation exceeded the value of the demolition services provided. Since the house in the case before the court had to be destroyed anyway to make room for its successor, its value was negligible and didn’t exceed the value of the demolition services that the owners received, so the homeowner’s charitable deduction was denied.

    Fire

  • 15. Non-Profit Lie

    After purchasing residential property, a couple wanted to tear down the existing home and build a new one. The old structure was conveyed to a nonprofit that hires disadvantaged people to deconstruct buildings and salvage materials. The conveyance was not recorded in the state’s land records by either the couple or the charity. The couple took a charitable write-off for the house’s full value. But an appeals court axed the deduction, saying the fact that the couple didn’t transfer their entire real property interest precludes claiming any deduction for the donation.

    Destroy Building