1. Free Beer
In 1982, the U.S. Tax Court allowed a service station operator to deduct the cost of beer he offered to his customers free of charge while their vehicles were being filled with gasoline or serviced.
2. Fake Boobs
In 1988, exotic dancer Cynthia Hess, aka Chesty Love, claimed a $2088 depreciation on surgical implants that enlarged her bust to 56FF. A trial judge ruled that the breasts are so large and cumbersome (10 pounds each) that she could not possibly derive personal benefit from them.
3. Cat Food
Junkyard owners were able to deduct cat food as a legitimate business expense. Apparently they would leave food out to attract feral cats that would eat or otherwise chase off rats, snakes and other pests.
4. Swimming Pool
A taxpayer with emphysema was allowed to deduct the cost of a pool as a medical expense (as its primary purpose was for medical care) as well as the cost of heating the pool, pool chemicals and other pool maintenance.
5. Body Oil
In 2004, Wisconsin bodybuilder Corey L. Wheir filed suit against the IRS after the agency denied his deductions for bison meat, supplements, body oil and tanning products. While he didn't get the high protein meat or the supplements, he did get his ProTan Muscle Juice Professional Posing Oil, which he applied to his body prior to going on stage, as a business expense.
6. An African Safari ... for Dairy Cows
The owners of a dairy business went on an African Safari and tried to write the cost off as a business expense. They justified the deduction by saying that many of the dairy's promotional activities and marketing efforts included wild animals. The IRS agreed that the trip was "ordinary and necessary," and the deduction was allowed.
7. Clarinet Lessons
In 1962, at least one family was able to convince the IRS to allow them a deduction for their kid's clarinet lessons. The deduction went through because the child's orthodontist wrote a letter verifying that clarinet lessons would help to correct the child's overbite.
8. Fancy Dresses
40's & 50's celebrity Dinah Shore claimed some formal dresses on her tax return and the IRS immediately cried foul. She claimed that the frocks were business expenses as she only wore them on her TV show and couldn't possibly wear them for personal reasons as they were too tight to sit down in. The IRS agreed but sent a representative to judge which dresses really were too tight to sit down in.
9. Private Airplane
Rather than drive five to seven hours to check on their rental condo, one couple bought their own plane. The Tax Court allowed them to deduct their condo-related trips on the aircraft, including the cost of fuel and depreciation for the portion of time used for business-related purposes.
10. Tricked Out Amish Buggy
A CPA in Amish country was able to deduct a pimped out buggy for one of his clients. The stock buggy was easy, as it was a business expense. What wasn't so easy were the dash lights, kick plates, dimmer switches, speedometer, hydraulic brakes and tinted windshield.