With so many of us racing against the clock to get those tax returns in by mopd, it's almost a given that there's going to be some cive bookkeeping along with those 1040s. Creative or just plain dumb?... See More
With so many of us racing against the clock to get those tax returns in by mopd, it's almost a given that there's going to be some cive bookkeeping along with those 1040s. Creative or just plain dumb? Here's paula faris. Reporter: Albert einstein allegedly said, "the hardest thing in the world to understand is the income tax." Well fear not, uncle albert, because uncle sam does occasionally have a soft spot for brilliant minds like yours who come up with imaginative deductions. Case in point, topless dancer and model chesty love. That's not her real name and those aren't her real breasts, on "jerry springer." She argued with the irs that her size 56n implants -- I said "n" as in "no kidding" -- were necessary stage props for her career as an exotic dancer and model. The irs originally had no love for chesty, until a tax court sided with her, saying her "freakishly large breasts" were part of her business "costume." Might not be as sweet in the new year. Reporter: Anietra hamper, a former anchorwoman in ohio, had a business costume, as well. And her expenditures were even bigger than chesty's. Over four years, she wrote off $90,000 and was audited. Didn't you think that was going to be a giant red flag? Here's what I know. It cost me a lot of money to keep my job. Reporter: The first expensive write-off? I had to buy specific shoes, SPECIFIC JEWELRY. Reporter: An on-air wardrobe she says she wouldn't be caught dead in off-air. She challenged the audit in court, where documents show she even wrote off lingerie, you know, no unsightly lines on tv. Then there's - your makeup. Have to have it. As you know, high definition television changed our lives. And, you know, it's expensive. Reporter: I too spend a lot oney on makeup and hair. Manicures manicures, too. I admit if I didn't work in the business, I would still get a lot of these services done, which is why the irs told her, "nice try." It is ordinary and reasonable? Reporter: This familiar face from h and r block explains. He's got the 411 on that 1040. If you're getting your hair done into a 19th century look, 18th century look for an audition or for a performance, then you can deduct it. But if you're just getting your hair cut on a regular basis to look good for tv or whatever, then it's not going to be deductible. Reporter: Know what else is not going to be deductible? Spending 65 grand on hookers. But that didn't stop this brooklyn lawyer from claiming it as a medical expense. For stress relief. Still, it isn't always black and white. It does sometimes pay to fight the irs. Think this woman could claim $12,000 in charitable expenses to care for 70 feral cats in her home? The irs got purrrsnickety, but she prevailed. Or, think this pro bodybuilder tread a slippery slope when he wrote off high-end body oil? A tax court thought he was pretty slick, but agreed -- those burnishing biceps are a piz business expense. And what about the california man who totaled his $40,000 truck driving while under the influence? When he wrote it off, the irs blew a gasket. But he won when a judge ruled, yeah, it's negligence, but not gross negligence. So much for, you booze, you lose. Meanwhile, back in ohio -- the irs taking a second look at anietra's taxes. Her on-air expenses were looking more like hot air. Bedding, contacts and contact lens solution, a robe, teeth whitening. She admits some those were submitted by mistake. I have nothing to hide. I did everything right. What I did was follow my accountant. Reporter: And then where is your accountant when the irs s after you? Gone. Reporter: Gone, too, is anietra's face from the evening news. She now runs a tourism website where no one will care what she looks like sitting behind a keyboard. For many people, if they've taken deductions that they're not entitled to, they're going to end up with a bill. And nobody likes that idea. Reporter: So, while some americans may forever try to push their luck, one thing the irs never lets slide -- well, my advice to people finishing their taxes this week is, by all means, finish your taxes this week.
This transcript has been automatically generated and may not be 100% accurate.