(ABC News) — When tax season rolls around, there’s always at least one thing people wish they could claim, but aren’t really sure. In some cases, crazier gambles lead to a big payoff. There are some strange, even entertaining, ways people are cashing in.
“There are two camps: the odd, really odd deductions that people try to take and don’t get away with, and then in some instances, there are the odder ones that people do get away with,” said Richard Gartland, a senior tax advisor at H&R Block.
Elective plastic surgery is generally a no-go zone for the IRS, but an exotic dancer deducted the cost of her breast implants. The tax court agreed it was a business deduction.
One man turned his drunk driving crash into money back. After his insurance company refused to cover the damage to the car, he deducted the cost of repairs as a casualty loss on his taxes.
“He was reimbursed, but what he had to pay in fines and going to classes to get him out of deep dutch with the police is, however, not deductible,” said Gartland.
Unusual medical deductions can also pay off. Boarding school for a child with respiratory problems? Good to go. Clarinet lessons to deal with overbite? Approved.
Another expense parents pay for, the babysitter, could also be claimed. It won’t work for date night, but if you’re off doing volunteer work, you might be able to claim the expense under charity.
Sometimes pet lovers can write off the cost of food.
“Cat food used to attract feral cats to a business location to keep down snakes was a deduction,” said Gartland. “It was a business deduction, not a loving, caring pet deduction.”
Sometimes it’s worth a shot, but many of these cases had to be settled in tax court. Trying could mean years before seeing any money back.