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Bankrate's 2008 Tax Guide
Filing & refund
Get it done right the first time with this advice on free filing, e-filing, documentation and refunds.
10 wackiest tax deductions
10 wackiest tax write-offs

Did you hear the one about the pot dealer's tax return? The New Yorker who claimed the whole city as a dependent? The exotic dancer who deducted ... well ... you know?

That's right, it's time once again for Bankrate's 10 craziest tax write-offs you've ever heard, presented as a shot of levity to help make filing your annual federal income tax return a little less tedious.

In our first installment, taxpayers sought deductions for everything from ostrich breeding to sperm donations. In round two, a high-tech breast pump and a pimped-out Amish buggy led the list of questionable claims.

But this year's strange-but-true collection from Certified Public Accountants around the country may be the most bizarre yet, not only for their sheer audacity but also for the few that managed to slide by the IRS.

Of course, it is no laughing matter to try to knowingly defraud Uncle Sam. Serious consequences await those who fail to file, falsely file, knowingly underreport or otherwise play fast and loose with their federal income tax return. Watch "Odds of being audited"

It's also just plain dumb. What -- like the IRS doesn't know that deductions are the biggest temptation in the tax code?

"In my business, as the saying goes, 'Pigs get fed, hogs get slaughtered.' If you want to deduct something, just don't be overly aggressive with it. It's everything in moderation," advises Walt Hatter, CPA of Hatter & Associates in Fort Worth, Texas.

"You want to look at your returns in the same way your physician looks at your heart rate -- you want it to be about the same all the time. When it starts moving around a lot, the IRS wants to see why. When you have big swings in income or big swings in deductions, the IRS likes to check to make sure you're still alive. They're going to come take your pulse, and you might get a full body probe."

To avoid the, uh, full body probe, best to steer clear of these crazy tax tactics!

Daffy deductions
In case you're thinking of tempting fate -- or the IRS -- remember: Pigs get fed, hogs get slaughtered.
10 wackiest write-offs
1. It went up in smoke
2. No receipts from above
3. Silence is golden ... and deductible
4. He took Manhattan, the Bronx and Staten Island, too
5. But you can write off the pimp hat
6. The "Zoolander" deduction
7. What are you, an Indy driver?
8. The $50,000 business meeting
9. Finally, the Social Security crisis solved!
10. Inflating your assets
-- Posted: March 21, 2008
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