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.

#6. Bar Declares Everyone to be Actors to Circumvent Smoking Ban

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.

"...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.

"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.

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.

#5. Man Flies Free Thanks to Pudding

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.

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.


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?

#4. Guy Rips Off a Game Show by Being a Slacker

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.

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.

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

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