The Internal Revenue Code is packed with thousands of tax deductions, from write offs for unreimbursed medical expense to deductions for cheese baskets for clients. But because nobody wants to pay more than their fair share of taxes — and because the Tax Code is often dizzyingly complex — it’s the time of year when even honest taxpayers may find themselves considering “imaginative” deductions. Some are totally legit; others are completely ridiculous, such as when Leona Helmsley attempted to deduct the cost of underwear as a business expense.
That’s not to say that the IRS hasn’t let slide a few wacky deductions – click here to see eight offbeat tax deductions that have actually worked. Careful, though: the IRS considers each taxpayer’s situation individually — and there are many exceptions to every tax rule. If the Feds disallow your deductions you could be subject to penalties and interest charges, so consult a tax expert before you get too creative. In the meantime, enjoy these inventive deductions.
PHOTO GALLERY: The 8 Craziest Tax Deductions Approved by the IRS
A version of this piece originally ran on April 15, 2011.