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Supreme Court Justice Oliver Wendell Holmes called taxes “the price we pay for civilization.” But he never said we have to pay retail! As April 15 approaches, let’s take a look at what some of our favorite bold-face names might deduct this year:

Tiger Wood’s Sex Rehab. Previous winners in the celebrity “rehab” category have struggled with booze and drugs. But golfer Tiger Woods breaks new ground with his addiction to Vegas cocktail waitresses. Rehab costs are a deductible medical expense. Good thing Tiger can still drive his ball 300 yards without hitting a tree!

Jon & Kate Plus Divorce Lawyer. Why is divorce so expensive? Because it’s worth it! Especially when your ex makes off with $235,000 from your joint account! Most of the Gosselin’s divorce attorney fees are nondeductible personal expenses. But they can still deduct legal fees for determining tax-deductible spousal support.

Conan O’Brien’s Job Hunt. Conan worked decades to earn his dream job hosting “The Tonight Show,” then lost it just seven months later. Fortunately, job-hunting expenses (including hair gel and internet access to write letters to the “people of the earth”) are deductible as a miscellaneous itemized deduction. [click to continue…]

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