Exotic dancer Cynthia Hess -- better known as "Chesty Love" -- made tax law history in 1994 when she successfully sued the IRS to take a $2,088 deduction on a boob job that left her with a size-56FF chest.
U.S. Tax Court Judge Joan Seitz Pate noted that Hess increased her income as a result of the surgery and that her cumbersome breasts, weighing 10 pounds each, were so large that she could not derive personal benefit from them. Hess had undergone the surgery "all for the purpose of making money" at an Indiana strip club, and the tax court allowed her to deduct the expense as a "stage prop."
5. Making whoopee can pay. If your doctor prescribes sex therapy, the cost can be deducted as a medical expense, says Lyons. Unfortunately, the IRS won't let you write off a health club membership, even if your doctor and spouse agree that you need to go to a gym.
Taxpayers have obviously tried to write off many healthful activities. In one celebrated tax law case, the cost of clarinet lessons was ruled to be an acceptable deduction, after an orthodontist recommended that a child learn the instrument to correct a severe overbite.
But the IRS has rejected many unorthodox medical expenses. H&R Block lists the following:
Dancing lessons: A 1964 ruling disallowed dance lessons as a medical expense to improve varicose veins. A later ruling disallowed dancing as a medical expense to ease arthritis and nervous conditions.
Diaper services: "Very convenient, but not an allowable medical deduction," H&R Block says.
Salad: The cost of lettuce and tomato not deductible as medical expense for a diabetic on a restricted diet, according to a 1966 court ruling. The same taxpayer also tried to deduct artificial sweeteners and reduced-salt foods. He was likewise denied.
A fallout shelter: Useful in a nuclear war, but not deductible as "preventive medicine."
6. Legitimate expenses of illegitimate businesses: If you're selling marijuana and cocaine, you can deduct legitimate business expenses. That would include paper clips and office supplies, baggies to package the merchandise, and so forth.
"Just remember, the IRS expects you to declare all your illegal drug income," says Miami-based forensic accountant Stanley Foodman. "Once you're busted, there are tax ramifications."
Illegitimate business expenses -- smuggling contraband, kickbacks to rogue law enforcement officers, etc. -- can't be deducted.
Foodman says he's actually had clients who've listed illegal businesses on their tax returns. One woman described her occupation as "prostitute."
"She wanted to declare all her income and set up a retirement plan," Foodman says. "She was very up-front about how she earned her money."
Many states are getting very specific with taxes on illegal drug sales, so that dealers, once caught, get slapped extra hard for their ill-gotten gains.
In January, Tennessee joined a handful of other states that charge sales tax on illegal drug sales. Among the new tax rates: a $50 per gram tax on cocaine and a $3.50 per gram tax on marijuana (other than stems).
"Luckily for conscientious dealers, the law does not require them to give the names and addresses of their clients," jokes John Abolins, senior vice president of operations at Taxware.com, a provider of tax calculation software.
"It's one more way that governments say crime doesn't pay."
7. Don't soil your tax return. One final tip: When you send in your taxes, don't attempt to be a practical joker.