With tax season upon us, you may be thinking of some “creative” deductions to make your bill a little smaller. But we’re hoping they aren’t this creative.

CNNMoney talked to some tax preparers to compile a list of the craziest things people have tried to write off over the years, and if the items themselves are silly, wait until you hear about the rationale behind them. Here are a few of the best:

Playboy subscription- A doctor tried to pass this one off as a legitimate business expense, thinking that since his waiting room magazines were fair game, why not Playboy too?

Victoria’s Secret lingerie – The owner of a tree-cutting company included receipts for a few hundred bucks in lingerie along with the money he spent for hardhats and such, and called them all “protective clothing.”

Pole dancing classes- A man who spent $800 on his wife’s pole dancing classes wanted to write off the expense as “meals and entertainment,” saying that watching her dance helped him relax and made him better at his job.

Recreational drugs – The bookkeeper for a rock band tried to deduct five figures worth of illegal drugs as “travel & entertainment” expenses, claiming the cost was “necessary and ordinary.”

Eh, it’s always worth a try.

[Via CNNMoney]

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