Every year, taxpayers try to slip things into their taxes as deductions, things they might deem necessary business expenses that can be written off. Some of these things fly with tax preparers and subsequently, the Internal Revenue Service, while others, say, a subscription to Playboy, just don’t.

CNNMoney presents an entertaining list of some of the craziest things tax preparers have seen through the years, from the aforementioned nudie magazines to recreational drugs for the purposes of a band’s “entertainment” expenses.

Check out a few below, and the complete list over at CNNMoney.

Carrier pigeons: One man had such a phobia of using modern technology, he refused to use a phone or computer. So of course, when he had to communicate with his business partner across town, he decided to use carrier pigeons. Turns out the deduction was fair game, said his tax preparer, as it’s the only way he talks to his business partner, and never used technology in the past for such a purpose.

Playboy magazine subscription: There’s sometimes a dearth of interesting reading material to choose from at the doctor’s office, so one physician took it upon himself to deduct the cost of a Playboy subscription as a business expense along with the normal fare like say, Highlights.

Unfortunately for him, his tax preparer found there was “no business purpose for a doctor to be reading a Playboy magazine and this is not the type of reading material you would want to leave lying out in the waiting room for patients — perhaps even children — to read.” Deduction denied!

Victoria’s Secret lingerie is not protective clothing: A man who owned a tree-cutting business wrote off a few hundred dollars worth of ladies unmentionables from the popular store, as well as his normal protective clothing for the job. Unfortunately, his tax preparer caught the attempt at slipping those undies under the radar, and removed them as a business expense.

Recreational drugs: This one would seem like a no-brainer, but one financial planning firm said they had clients in a rock band who submitted a deduction labeled “drugs” as “travel and entertainment” expenses. The cost was in the high five-figures, and weren’t disguised as prescription or medical drugs.

“The band’s bookkeeper had concluded that the cost of recreational drugs was necessary and ordinary,” said the preparer. “Apart from admitting to possession of illegal drugs, the IRS would strongly differ with their tax position.”

Craziest tax deductions [CNNMoney]

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