The 6 Most Creative Abuses of Loopholes

Now, we're not saying that cheaters win. We're just saying... well actually we are saying that. You just have to be really good at it.
The 6 Most Creative Abuses of Loopholes

The best way to get away with cheating isn't to avoid getting caught... it's to technically not do anything wrong, and still get all the rewards. That's where you find the line between lawbreakers and those who simply think outside the box... and that line is very thin indeed.

Bar Declares Everyone to be Actors to Circumvent Smoking Ban

The 6 Most Creative Abuses of Loopholes

Back in 2007, Minnesota followed a national trend by passing an anti-smoking law that banned smoking in pretty much every public building, including bars. Unfortunately, that was bad news for the bars, because if you're going to get good and drunk to fight off the depression manual labor and seasonal affective disorder brings, you want to get your smoke on, too. Nobody wants to go stand outside to smoke, since in Minnesota it gets cold enough at night that neurons stick open and thoughts freeze in your head. So, that winter, the customers stayed home.

The 6 Most Creative Abuses of Loopholes

"...or, we could get stoned and play Xbox."

The good owners of the Barnacles Bar were determined to find a loophole that would let their nicotine-addicted clientele feed their deadly vice in peace. They found it:

There was a line in the law that said if you were an actor in a play, and your character smoked, then you'd get a pass. You know, like if you were doing a live stage show of the X-Files and you were playing the main bad guy. Thus, the owners of the bar declared that they were staging a continuous live performance and that everyone in the bar was an actor.

The 6 Most Creative Abuses of Loopholes

"Now can I fucking smoke?"

The thing was, the law didn't bother to specify what was meant by "stage performances," and really, how do you argue? So what if they didn't have a script--there is such a thing as improv. So what if they weren't getting paid--the law didn't say only professional actors counted. So, you enter Barnacles on a Saturday night, and then see that the staff are in costume and that you have become a performer in their "Theater Night." Sure, you don't have any lines and you're probably just playing "Guy Drinking To Forget His Job #5," but, hey, you need to smoke to get into character.

The 6 Most Creative Abuses of Loopholes

This started a movement, with bars in other states under similar bans trying the same tactic. The authorities aren't amused and have levied fines against the bars for violating the ban, which several are challenging in court.

Man Flies Free Thanks to Pudding

The 6 Most Creative Abuses of Loopholes

It really does pay to read the fine print. Just ask David Phillips, a University of California civil engineer. In 1999, he noticed that on the box of one of his Healthy Choice frozen dinners, next to the part that presumably warns you against actually putting a Healthy Choice frozen dinner in your mouth, was a promotion they were doing with an airline. Anyone who sent in 10 barcodes from the frozen dinners would get 1,000 frequent flyer miles in return. Get enough of those miles and the airline lets you fly for free.

The 6 Most Creative Abuses of Loopholes

Which we're told can save you valuable money for local prostitutes and strange foreign drugs.

Being a huge math geek (which is shocking for someone who sits alone reading the writing on a tray of microwave chicken), he did some calculations and realized that 1,000 miles had way more value than some of the cheaper products in the Healthy Choice line---namely, 10 servings of Healthy Choice pudding. So, he jumped into a van and literally bought every single cup of pudding he could find.

Phillips purchased 12,150 cups of pudding in all, and to avert suspicion at the stores he simply said he was stocking up for Y2K.

The 6 Most Creative Abuses of Loopholes


Healthy Choice, clearly not anticipating that much interest in their product, resisted but all the same ended up forking over the 1.25 million miles to Phillips.

Not only that, Phillips also got the Salvation Army to peel off most of the barcodes for him, in exchange for donating the pudding--which earned him an $800 tax deduction on top of everything. For around two thousand bucks, David Phillips and his family have been flying free for years.

But life isn't all roses: The downside to all this is that Phillips' story inspired a film called Punchdrunk Love... where he's portrayed by Adam Sandler.


We ask you: Was it worth it?

Guy Rips Off a Game Show by Being a Slacker

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Having nothing better to do than watch game shows all day and silently wonder what went wrong with his life, unemployed ice cream truck driver Michael Larson was in the perfect position to pull off one of the greatest stunts in the history of afternoon programming.

His target was a popular CBS game show called Press Your Luck.


Press Your Luck basically consisted on a roulette wheel with light-up cartoon characters corresponding to different prizes. You get so many turns and if you hit the wrong spot, you lose everything. Hit "free turn" and you get to go again. So sort of like Wheel of Fortune, only without the spelling and the wheel was electronic. That latter part would be their mistake.

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One of their mistakes.

See, it's actually pretty hard for a computer to generate truly random patterns. Since Larson watched the show every damn day, eventually he noticed that the roulette only had six patterns of lights. So, he carefully taped each episode and, using the prodigious memory he had acquired reciting ice cream flavors, he memorized the six patterns and figured out exactly when to hit his button to make it land on whatever space he wanted, including "free spin." That's also important: The show had no rules limiting how long the game could go on. You could Free Spin forever. Larson had figured out a way to win basically infinite money.


Then he flew to LA and managed to get on the show. When his turn at the board came around, he won, and won, and won. He won $30,000, and by that point had been playing for longer than the half hour the show was allotted to air. They actually had to stop the episode and bring him back the next day to continue the round. When they did, he kept winning.

He wound up with over $100,000, a trip the Bahamas, and the undying hatred of a game show's producers.

They got off lucky; the only reason his run ended was because he eventually declined to spin again (the show let you hand off your turn to the next contestant) and fatigue was making him start to miss his mark. By then CBS figured out what he did and tried to have him disqualified, but nothing he did was illegal. He just beat their system. Their stupid, stupid system.

They changed the board patterns and banned the Larson episodes from airing as reruns. Meanwhile, Larson walked away with a nice pile of cash... only to lose it all in an investment scam. But, hey, a free trip to the Bahamas and the memory of punking a major network? Priceless.

The 6 Most Creative Abuses of Loopholes

His beard elected to stay behind and reign as an island king.

Junk Mail Checks Turn Out To Be Cashable

The 6 Most Creative Abuses of Loopholes

Like everybody else who was alive in the 90s, Patrick Combs, a career consultant, was constantly being bombarded by junk mail letters advertising relatively innocent scams (at least compared to today's excessively familiar penis-enlarging-haiku-spammers).

ACL TUE UNTOUE MOVA SLLAINC OPPORTEND yo TAE 90 WE TOOK IN... $95,093.35 IN JUST 3 WEEKS AND I'LL SHOW YOU 10T na vet es yn teal ti idt. We tonede 110

A long way from "RE: ur d1ck will explode _____R_O_L_E_X_".

The massive junk mail industry created a sort of arms race; recipients got used to just dumping the mail in the trash, so these shady companies would try more and more extreme gimmicks to get your attention. You'd get ads that looked like bills, ads that looked like late payment notices and ads that looked like checks.


And, of course, Czech ads.

For instance, one of those letters was a "work-from-home" gimmick that came with a fake check for $95,000 made out in the recipient's name. Combs, maybe just wanting to see what would happen, deposited that bastard into his account. The next day he found he had the $95,000 in his account. He giggled and figured that the bank would take it back. They didn't. A few weeks passed. The money was still there.

Combs started reading up on checking laws and discovered that, due to a technicality, the fake junk mail check actually counted as a legitimate financial instrument. They had been so dedicated to making the check look real that they didn't realize that simply writing "non negotiable" in tiny print in the corner was not enough to render it null and void. The check was valid, Combs simply been the first guy silly enough to deposit one. And his bank had been stupid enough to cash it.

The 6 Most Creative Abuses of Loopholes

So, he withdrew the money from his account. No longer a bunch of extra zeroes on a computer screen and now actual money, the bank realized that, holy shit, they had just honored a huge check from a fly-by-night scam operation that didn't actually have the kind of cash to back it up.

Unfortunately for them, by the time the bank realized what had happened, their window for getting the money back had already passed. So, naturally they tried to persuade Combs to hand over what was now legally his by bullying him, saying he was guilty of fraud and that they were going to send the cops after him. But no crime had been committed. Combs went to the media, his story appearing in the Wall Street Journal and from there, everywhere. He was on Good Morning America and just about every other news show on TV. He did speaking engagements and he even made a DVD of his story the he sells at his site.

The 6 Most Creative Abuses of Loopholes

He also works as a motivational speaker.

Eventually his conscience got the better of him and Combs returned the money, after getting the bank to write a letter admitting they had acted like dicks. After months of insisting that "non-negotiable" on a check indeed rendered it invalid, Combs amused himself by paying them back the money with a check with the same "non-negotiable" written in the corner. The bank took it with no problem.

Australian Farmer Named Royalty by Accident

The 6 Most Creative Abuses of Loopholes

In the late 1960s, Leonard Casley grew way too much wheat, which could only ever be a serious problem if you live in Australia. You see, Australia had wheat quotas at the time and Hutt River (the province where Casley and other families grew) had inadvertently surpassed it, meaning they weren't allowed to sell any of it. When they petitioned for the quota to be raised, the governor responded by saying, "No," and filing a law to take their land away. THAT'S how serious Australians are about wheat.

The 6 Most Creative Abuses of Loopholes

Wheat and dingoes are two things they never take lightly.

In a desperate attempt to delay the legal process, the five families of Hutt River seceded from Australia under the Treason Act of 1495. This would have been as pointless as that time you were five and told your mom you were leaving home... if the government hadn't accidentally referred to Casley as "Administrator of Hutt River Province" in official correspondence, which actually gave him legal recognition as a ruler under Australian law. Yes, in Australia, calling someone something magically turns them into that.

The 6 Most Creative Abuses of Loopholes

His full legal name is now "Hugh J. Wolverine."

Taking full of advantage of the mistake, Casley declared himself His Majesty Prince Leonard I of Hutt, meaning it was now treason, under Australian law, to charge him with any crime or interfere with how he ran his new country.

The 6 Most Creative Abuses of Loopholes

Prince Leonard can make it so all dudes have to wear necklaces, if he wants to.

Could Australia have stopped him? Sure. But by the time they got around to it, the statute of limitations had run out. So as of 1972, The Principality of Hutt River had officially seceded from Australia and stopped paying income taxes.

As of the modern day, Hutt River is still separate, while Australia treats it as a private business that doesn't pay them taxes and just tries, really hard, to pretend it's not there.

The 6 Most Creative Abuses of Loopholes

In all fairness, it's a pretty small chunk.

Redefining Auto Racing Through Cheating


While racecar mechanic Smokey Yunick never technically broke the rules in NASCAR back in the 1960s, he perfected the art of plunging headlong into every single loophole in the regulations. In NASCAR slang this is still known as "Yuniking the rules"; for the rest of the world it's just "being awesome at cheating."

The 6 Most Creative Abuses of Loopholes

The whole point of NASCAR racing is that every car is the same; race officials carefully inspect the cars to make sure this is the case. It's supposed to be all about the drivers and the strategy--primarily based on fuel consumption, and figuring out how to go as long as possible between time-consuming pit stops. Once, when inspectors had removed Smokey's gas tank to make sure it was regulation size, he climbed in the supposedly gasless car, started it, and drove off.

He wasn't using black magic; it turned out he had replaced the fuel line with a coiled tube that could hold five gallons of extra gas. Yeah, they'd forgotten to make a rule about that. Then when inspectors would drain the fuel to just see if he was hiding any, it'd come out just right--that's because Smokey had put a basketball inside the tank and inflated it before inspection. After inspection, he'd let the air out of the ball and now he had an extra cubic foot or so of fuel tank to work with.

The 6 Most Creative Abuses of Loopholes

This is actually his combination race-car/BBQ.

That was just the beginning. He figured out how to improve the aerodynamics of the car while creating the optical illusion that nothing had been changed. He invented so much stuff to try to sneak in an extra edge here and there that you probably have some of it in your car now. He was awarded a dozen or so patents for his innovations in steering systems, spark plugs, cooling and probably some kind of hidden rocket booster. He's now in the Motorsports Hall of Fame.

The 6 Most Creative Abuses of Loopholes

They even drew this badass picture of him.

Now, we're not saying that cheaters win. We're just saying... well actually we are saying that. You just have to be really good at it.

For more "cheats," check out The 7 Ballsiest Sports Cheats Ever. Or learn about some perceived assholes that weren't all that bad, in 6 Historical Villains Who Were Actually OK Guys.

And stop by Linkstorm to see how you can cheat your way to having more friends on Facebook. is looking for a lead PHP engineer to join our team of award-winning badasses. For more info, go here!

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