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Celeb Tax Perks: Can Nelly Deduct His Grillz?

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Stars like Clooney are often in a position to expense trainers and nutritionists. And if he takes a part as a golfer, he may even require extra tee time with a pro to get into character.

The IRS clearly recognizes such professional expenses. But you'd better be able to make your case, if you get audited and want to pass yourself off as a part-time thespian preparing for roles as a day spa junkie.

Q: Is Star Jones' Breast Augmentation a Business Expense?

Normally, cosmetic surgery is not deductible. However, if you can prove you need breast implants to do your job, the government might just let you write off your cosmetically enhanced chest as if it were part of your work uniform.

In a landmark tax court ruling from 1994, exotic dancer Cynthia Hess — better known as "Chesty Love" — 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."

But this certainly isn't the blanket rule for all entertainers. "You have to be able to ask, is the surgery necessary to fill a specific role," Shannon says. "And, obviously, sometimes the answer is yes."

In Jones' case, she might have a tough time making the argument that it was a business necessity. But plastic surgery can be considered a medical deduction if it is done to correct an injury, ailment or birth defect.

When asked about the procedure late last month, Jones said, "Let's just put it like this . . . two weeks ago was my 44th birthday but my (breasts) think they're still 20." That might not be the explanation the IRS is looking for.

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