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Am I Required to Report My (Unconventional) Income to the IRS?

Ah, taxes. They’re unavoidable, often painful to think about, and take a nice chunk out of everything that we earn. (Thanks, Uncle Sam.) If you are a W-2 employee, your employer skims your taxes off of your paycheck, so you never even see that money — but what if your income sources are more, ahem, unconventional?

In general, if you have to ask whether you need to report certain income to the IRS, the most likely answer is, “Yes.” Here are some less-than-typical (we hope) examples where you’re going to need to pony up, courtesy of MSN Money.

Q. I hosted a party to sell products to my friends (using my social circle for multilevel marketing for some corporation), and the company’s representatives brought me gifts. Do I have to report this?

A. Yes.

If you host a party at which sales are made, any gift you receive for giving the party is a payment for helping a direct seller make sales. You must report it as income at its fair market value.

See Publication 463.

Q. My sugar-daddy (er… loving husband) died and I had to pay to collect the reward (er… life insurance). Do I have to report this?

A. Yes.

Life insurance proceeds paid to you because of the death of the insured person are not taxable unless the policy was turned over to you for a price. This is true even if the proceeds were paid under an accident or health insurance policy or an endowment contract.

Learn More: How to Avoid Estate Taxes on Life Insurance Proceeds

Q. This year, I’ve been taking bribes to keep the caviar smuggling ring off the FBI radar. Do I have to report this?

A. Yes.

If you receive a bribe, include it in your income.

Q. I ran for office this year and used campaign contributions to pay for my second cousin’s bodyguards and my daughter’s wardrobe. Do I have to report this?

A. Yes.

These contributions are not income to a candidate unless they are diverted to his or her personal use. To be exempt from tax, the contributions must be spent for campaign purposes or kept in a fund for use in future campaigns… Excess campaign funds transferred to an office account must be included in the officeholder’s income on Form 1040 in the year transferred.

Q. Instead of buying a Hummer for $70,000, I paid $80,000 for the vehicle and received a $10,000 rebate. Do I have to report this?

A. Yes, well, sort of. When you sell the car, figure your loss by using the sales price of $70,000, not $80,000.

A cash rebate you receive from a dealer or manufacturer of an item you buy is not income, but you must reduce your basis by the amount of the rebate.

Related: How to Intelligently Buy a Car

Q. I successfully sued a hip hop artist for sampling my music. Do I have to report this?

A. Yes. The article goes into detail to determine what kind of income is reportable.

To determine if settlement amounts you receive by compromise or judgment must be included in your income, you must consider the item that the settlement replaces.

Q. I successfully sued my boss for emotional distress. Do I have to report this?

A. Yes.

If the emotional distress is due to a personal injury that is not due to a physical injury or sickness (for example, employment discrimination or injury to reputation), you must include the damages in your income. The exception being any damages you receive for medical care due to that emotional distress.

Q. I lost my job and my credit card’s insurance stepped in and made my payments for me. Do I have to report this?

A. Yes.

Generally, if you receive benefits under a credit card disability or unemployment insurance plan, the benefits are taxable to you. These plans make the minimum monthly payment on your credit card account if you cannot make the payment due to injury, illness, disability, or unemployment. Report on Form 1040 the amount of benefits you received during the year that is more than the amount of the premiums you paid during the year.

Q. I received assistance from a non-profit program to help pay for the down payment of my house. Do I have to report this?

A. Yes.

If you purchase a home and receive assistance from a nonprofit corporation to make the down payment, that assistance is not included in your income. If the corporation qualifies as a tax-exempt charitable organization, the assistance is treated as a gift and is included in your basis of the house. If the corporation does not qualify, the assistance is treated as a rebate or reduction of the purchase price and is not included in your basis.

Q. I got a job with the help of a headhunter who charged me for his services. Do I have to report this?

A. Yes.

If you get a job through an employment agency and the fee is paid by your employer, the fee is not includible in your income if you are not liable for it. However, if you pay it and your employer reimburses you for it, it is includible in your income.

Q. I found an abandoned car and kept it while the person who lost the vehicle likely wept. Do I have to report this?

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A. Yes.

If you find and keep property that does not belong to you that has been lost or abandoned (treasure-trove), it is taxable to you at its fair market value in the first year it is your undisputed possession.

Q. My travel agency gave me a free tour of Paris. Do I have to report this?

A. Yes.

If you received a free tour from a travel agency for organizing a group of tourists, you must include its value in your income. Report the fair market value of the tour on Form 1040 if you are not in the trade or business of organizing tours.

Q. I hit the jackpot in Atlantic City. No one was around to hear the bells, I didn’t attract any attention, and I am sure there were no cameras in the casino. Do I have to report this?

A. Yes.

You must include your gambling winnings on Form 1040. If you itemize your deductions on Schedule A (Form 1040), you can deduct gambling losses you had during the year, but only up to the amount of your winnings.

Q. I split $54,000,000 in lottery winnings with 12 of my coworkers. Do I have to report this?

A. Yes.

Winnings from lotteries and raffles are gambling winnings. In addition to cash winnings, you must include in your income the fair market value of bonds, cars, houses and other non-cash prizes.

Q. I inherited a tenement and the tenants who I haven’t evicted are now paying rent to me. Do I have to report this?

A. Yes.

If property you receive this way later produces income such as interest, dividends or rents, that income is taxable to you. If property is given to a trust and the income from it is paid, credited or distributed to you, that income is also taxable to you. If the gift, bequest or inheritance is the income from the property, that income is taxable to you.

Q. I sold my comic book collection. Do I have to report this?

A. Yes.

If you collect stamps, coins or other items as a hobby for recreation and pleasure, and you sell any of the items, your gain is taxable as a capital gain. However, if you sell items from your collection at a loss, you cannot deduct the loss.

Q. I am a street pharmacist and all my income is cash. Do I have to report this?

A. Yes.

Illegal income, such as money from dealing illegal drugs, must be included in your income on Form 1040 or on Schedule C or Schedule C-EZ (Form 1040) if from your self-employment activity.

Q. I’m a doctor, and pharmaceutical companies pay me incentives to push their drugs. Do I have to report this?

A. Yes.

You must include kickbacks, side commissions, push money, or similar payments you receive in your income on Form 1040 or on Schedule C or Schedule C-EZ (Form 1040), if from your self-employment activity.

Q. I flashed my breasts at a wet t-shirt contest hosted by WTIT in a Miami Beach bar during spring break and won a prize. Do I have to report this?

A. Yes.

If you win a prize in a lucky number drawing, television or radio quiz program, beauty contest or other event, you must include it in your income. For example, if you win a $50 prize in a photography contest, you must report this income on Form 1040.

Q. I won the Nobel Peace Prize (in addition to being Time Magazine’s 2006 Person of the Year). Do I have to report this?

A. Yes.

If you were awarded a prize in recognition of accomplishments in religious, charitable, scientific, artistic, educational, literary, or civic fields, you generally must include the value of the prize in your income.

See Publication 525 for more information.

Q. I saw my girlfriend on America’s Most Wanted and ratted her out to the police. I collected a sizable reward for material information leading to an arrest. Do I have to report this?

A. Yes.

If you receive a reward for providing information, include it in your income.

Q. I bought art depicting dogs playing poker several years ago and sold the work this year to a rich idiot for a nice profit. Do I have to report this?

A. Yes.

If you sold an item you owned for personal use, such as a car, refrigerator, furniture, stereo, jewelry or silverware, your gain is taxable as a capital gain. Report it on Schedule D (Form 1040). You cannot deduct a loss… However, if you sold an item you held for investment, such as gold or silver bullion, coins or gems, any gain is taxable as a capital gain, and any loss is deductible as a capital loss.

Q. I found a bunch of LCD HDTVs, which I can only assume had fallen off a truck. I sold a few out of the back of my own truck. Do I have to report this?

A. Yes.

If you steal property, you must report its fair market value in your income in the year you steal it unless, in the same year, you return it to its rightful owner.

Learn More: Current Federal Income Tax Brackets & Marginal Rates

So, there you have it. If you come into money — earned, won, stolen, or found — chances are high that Uncle Sam wants his cut. You should probably err on the side of caution and report it all, no matter where or who it came from. Oh, and just return those LCD TVs that you “found.”

Can you think of any other situations in which you may not be sure whether you’re required to report your income to the IRS?

Published or updated February 10, 2017.

About the author

Luke Landes is the founder of shizennougyou. He has been blogging and writing for the internet since 1995 and has been building online communities since 1991. Find out more about Luke Landes and follow him on Twitter. View all articles by .

{ 23 comments… read them below or add one }

avatar 1 Anonymous

LOL! this was a very entertaining post — er, i mean educational. thanks for sharing it. i enjoyed it. :)

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avatar 2 Anonymous

Q: If you read a very entertaining (er..educational) post what should you do?

A: Promote it!

Make sure that you mention it on all your favorite social networks including Twitter, Stumble Upon, and Digg. ;)


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avatar 3 Anonymous

This post was hilarious!! It was great and had me laughing =)!!

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avatar 4 Anonymous

Wow, the government wants their hand on everything. Not condoning certain behavior, but it might be hard to verify certain prize earnings or rewards.

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avatar 5 Anonymous

Does anyone honestly believe most criminals report their illegal income?

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avatar 6 Luke Landes

Heh, I doubt it anyone believes that. But it does provide another path for law enforcement to go after criminals they can prove received income but they can’t quite prove they’ve committed a crime.

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avatar 7 Anonymous

When the Feds can’t make the real case against the criminal, they always check on income tax evasion – catches quite a few hard-core criminals.

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avatar 8 Anonymous


It’s there to help punish illegal actions, and to give the government extra “room” to investigate people they believe are doing illegal things. It’s not about taxes, but about finding a way to excuse extra-invasive investigations. It’s actually humorously clever. ;-)

Say, Flex, I’ve sent a few emails to you (I believe, at least) about a possible guest post. Have you received the emails? They might have been sent to the spambox, so I wanted to make sure you knew. :)

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avatar 9 Anonymous

Let me try this: I own a mutual fund in a country other than the US. I have double citizenship: US and that of the country where I own the mutual funds. On withdrawing my gains, the mutual fund company in that country automatically withholds the capital gains tax (according to that country’s tax regulations) and sends it promptly to the local tax authority.

Under these circumstances, do I still have to report the capital gains to the IRS even though I have already been taxed once for them? (If yes, what forms would I need to use?)

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avatar 10 Anonymous


(If Internet acronyms aren’t your thing, it’s Rolling On the Floor Laughing My Ass Off!) ;-)

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avatar 11 Anonymous

Ok. How about:

I dug a hole in the ground in the backyard of the house that I own and found a $10,000 gold nugget. Do I have to report this?

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avatar 12 Anonymous

perhaps that would increase your basis in the property? LOL

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avatar 13 Anonymous

Things may have changed, but about 20 years ago my mother was awarded a mega-dollar lawsuit when a guy struck her from behind while she was sitting in her car at a traffic light. She broke her neck, had internal brain injuries and had to learn to walk again. Her lawsuit proceeds were not taxable at that time according to her attorney, her accountant, and the IRS.

For the record, the guy was a VP for the largest privately owned insurance company in the state … and he was driving the company car. From the attorney’s point of view, it didn’t get any sweeter than that.

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avatar 14 Luke Landes

Ron: That’s a terrible thing to happen. I hope your mom has recovered fully. Prior to 1996, injury lawsuit settlements and awards were not reportable to the IRS, so 20 years ago she wouldn’t have to report the award and the attorney, accountant, and IRS were correct.

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avatar 15 Anonymous

Wow, this is hilarious. I’m starting to see how Al Capone got into trouble with the IRS:

Q: I’m running a massive criminal empire as one of the most famous (and infamous) people in the country. Do I have to report my income?

A: Yes. Or the IRS will succeed where every other law enforcement agency has failed and arrest you, inspiring constant quips from hundreds of commentators for decades about how you evaded the FBI and the police, only to be taken down by the IRS.

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avatar 16 Anonymous

FG– YES, you would report the capital gains to the IRS, on the same form you use to report domestic capital gains. But the good news is that you can get a dollar-for-dollar tax credit for the taxes you paid to the other country. The tax credit form is 1116.

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avatar 17 Anonymous

What section in the Internal Revenue Code does it say that you will be taxed on a reward that you receive for providing information that leads to an arrest?

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avatar 18 Anonymous

I sold all most my material belongings to create more cash flow for myself during a rough time. (TV’s, furniture, appliances, art, clothes, shoes) and gained a profit from everything I sold. It was reported last year by my tax preparer as self employment. Is this the correct classification? If not, how do I correct it or is it to late. (2010 return filed in 2011. I did not sell any stocks, bonds or anything like that. Just material goods as listed)

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avatar 19 Anonymous

How could you have gained a profit on everything you sold? Unless you sold all of your personal belongings for MORE than you originally bought them for? That’s not usually possible.

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avatar 20 Anonymous

I helped a lady with babysitting once in a while for extra cash, does it need to be reported.

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avatar 21 Anonymous

I’m disabled Because of Two car accidents and didn’t work but received money in a lawsuit and got loans I have no other income plus I lost alot of money in instant tickets do I file taxes and write off my losses

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avatar 22 Anonymous

If I use my company issued credit card for all my personal bills and shopping sprees, weekend get aways and any other personal expense, and then I claim that my boss gave me permission as a bonus for running his errands and picking his kids up from school (on 5 occassions), do I need to report my $4,000 a month bonus on my taxes?

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avatar 23 Anonymous

If I am a blind CEO. My employment contract provides for travel allowance in the amount of $600 a month for associated expenses the CEO commuting from his home to base office. The CEO travel allowance may include out of pocket reimbursements for taxis, drivers or other options. I do not keep copies of any receipts and do not provide accounting department with any supporting documentation.

Should the $600 be reported as income? Taxable income? Is there any ADA or IRS regulation that would exempt someone from reporting this income?

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