They tried to deduct what?!

From pornography to emu feathers, here are 10 of the wackiest things taxpayers have tried to deduct. Uncle Sam and the U.S. Tax Court were not amused.

Prostitutes

Sex with prostitutes is apparently not considered a legitimate medical expense. Who would have guessed?

A lawyer from New York kept track of his visits with prostitutes in a journal and tried to deduct their "services" as medical expenses.

The whopping $65,934 may have tipped off the IRS to a problem.

He also attempted to deduct nearly $5,000 for pornography and sex therapy books and magazines.

Unfortunately for him, the United States Tax Court found that the payments he made to prostitutes were illegal, and therefore not deductible.

As for the porn, the court ruled that "those amounts were incurred for petitioner's general welfare, not pursuant to a doctor's prescription or for a specific medical condition."

Emu Feather

So, an airline pilot and a massage therapist move their mobile home to a 78-acre lot of land in Tennessee and buy 20 chickens and two emus.

It may sound like the start of a joke, but it's not.

The couple would "from time to time" sell the chicken eggs -- $1 per dozen -- and emu feathers. They decided it was a business and deducted the cost of the animals' feed and maintenance on their taxes.

Unfortunately, they didn't record the income generated from these animals. So the court ruled that they didn't have a legitimate "trade or business" and therefore the costs weren't deductible as business expenses.

Candy and Flowers

A public defender from Santa Clara, Calif., attempted to deduct the cost of candy and flowers he purchased for secretaries.

But, surprise!

The IRS viewed these items as personal expenses and not necessary for a trade or business -- especially that of a public defender.

Buffalo Meat

A professional bodybuilder from Wisconsin once tried to claim buffalo meat, "posing oil" and protein shakes as business expenses -- adding up to more than $4,000.
He claimed he ate buffalo meat for muscle development because it has more protein than other meats -- and he consumed three pounds of the meat per day, year round, according to court documents.

But the court found the meat to be a personal expense because it can be eaten by anyone.

He was, however, able to deduct oils and tanning products, including ProTan Muscle Juice Professional Posing Oil, which he applied to his skin to "enhance his appearance."

The court allowed these items because they "were marketed only through bodybuilding publications and were not generally for sale through normal marketing outlets."

Underwear

A professional musician playing for rock star Rod Stewart's band once tried to claim men's underwear as stage clothes.

In addition to underwear, he tried to deduct silk boxers, leather pants, hats and a vest -- totaling $695. While he was allowed to deduct some of the "flashy" and "loud" items, the underwear were a definite no, the court ruled.

Loofa Sponges

A pilot from Franklin, Tenn., attempted to deduct loofa sponges as business expenses for his aviation activities.

Among the other "supplies" he tried to slip by the IRS were grass seed, a shower curtain and sporting goods items.

The court found that these were personal expenses and not necessary for his job as a pilot.

Aquarium

A couple from Rock Hill, S.C., tried to deduct a $1,150, 75-gallon saltwater aquarium as a business expense. The problem? The husband was a self-employed stockbroker.

As a result, the court found the aquarium -- along with a Magic Chef electric range oven and the re-covering of a sofa -- to be personal expenses, and therefore not deductible.

Sperm Donation

A doctor from Massachusetts tried to deduct thousands of dollars in costs for donating his sperm to in vitro fertilization.

But he was denied the deduction, with the court ruling that these donations did not affect his health or body and were therefore not legitimate medical expenses.

"Petitioner had no physical or mental defect or illness which prohibited him from procreating naturally...petitioner's choice to undertake these procedures was an entirely personal/non-medical decision," the court argued.

Nail Polish Remover

You would think a tax preparer would know better than this. But a self-employed tax preparer from Atlanta attempted to deduct nail polish remover, milk, beer and underclothes as business expenses.

But the IRS wasn't fooled, flagging the so-called "supplies" as personal items.

Scientology Class

A self-employed meat-and-seafood salesman from Sacramento, Calif., tried to deduct a class taught by the Church of Scientology as a business expense, saying it was necessary for his career.

He said that, in total, the 20-day class cost him nearly $1,500 between fees and travel.

The court held that the meat man could have read the same book at home and that that particular class was not absolutely necessary for his work.