In 1935, Edward A. Sparkman purchased two sets of dentures to stop a slight hiss that could have prevented him from receiving future work as an actor. (The second set was a backup so if one broke, he could still act.)
The courts ultimately said the expenditure was "nevertheless so purely personal in character" that it cannot be considered a legitimate business expense.
This is probably one of the most creative -- and shocking -- tax deductions out there.
Samuel T. Seawright and Carol A. Seawright had a little problem at their Columbia, S.C., junkyard: snakes and rats.
So the couple came up with a creative solution. They left out cat food to attract wild cats to the junk yard. Those cats would run off the snakes and rats.
So was the $300 they spent on cat food a legitimate tax deductions? Turns out it was.
Finally, we bring you one of the most obscure tax cases, which comes from Corey L. Wheir, a professional bodybuilder who tried to deduct high-protein buffalo meat, protein shakes and various kinds of body oils in 1999, 2000 and 2001.
Wheir ate three pounds of buffalo meat a day for muscle development. (If he had stuck to lower-protein beef, he apparently would have needed to consume six pounds a day.) He also consumed protein shakes.
He wrote off all that on his taxes as business expenses.
The court said "there is no doubt that buffalo meat is also consumed as food by nonbodybuilders, albeit not with the regularity and in the quantities consumed by petitioner." It ruled that his consumption was "inherently personal" and therefore not a legitimate deduction.
Additionally, Wheir used a number of oils to help him look better during competitions. The court found that the oils were a legitimate use for his business and, therefore, deductible.
So as you go through your taxes, consider some of these more unusual loopholes. As always, remember to consult a professional tax advisor. And the only reason we know about these deductions is because they all ended up in court.
With reports from Alice Gomstyn