Now, Kennedy Airport had recently installed a $100 million security system courtesy of defense contractor Raytheon. This system was designed to detect any potential terrorists who might attempt an aquatic landing. Little did Raytheon realize that their million-dollar mettle would be tested by one marooned jet skier whose nerves were hardened from an evening of boozing.

ABC News
"Hands? We didn't expect him to have hands!"

JFK's first line of defense was an 8-foot barbed wire fence, which Casillo managed to scale without any problem. He then channeled his inner James Bond and crossed two active runways while unintentionally thwarting a number of motion detectors and surveillance cameras. Next, he walked right up to the damn terminal and probably could have even boarded a flight if he hadn't finally been spotted by an airport staffer. At this point, JFK staff freaked the fuck out and cancelled 100 flights as a result of one confused man toddling around the runaway armed with nothing but a life jacket and poor life choices.

Jupiterimages/Comstock/Getty Images/Photos.com
"I'll be back in like an hour, be cool."

In an attempt to save face, the Port Authority police charged Casillo with criminal trespassing and pointed out that they had several clearly marked no-trespassing signs, which Casillo had the audacity to ignore (but which surely would have deterred any real wild-eyed terrorist).

To be fair to JFK and Raytheon, this is far from the first time the devil's nectar has defeated airport security. In 2004, a Scottish lap dancer named Soraya Wilson, galvanized simultaneously by a bender and a fight with her boyfriend, clambered up a barbed-wire fence at Aberdeen Airport and took a nap in a parked aircraft. It's unclear why news media at the time focused on Wilson's career as a lap dancer, but we're assuming her gyrating talents allowed her to python her way over razor wire without getting filleted.

BBC News
It's a good thing terrorists can't dance for shit.

Sure, the TSA staff who man the baggage scanners at the airport might not be top-of-the-line law enforcement, but everyone in the building has, if nothing else, been background checked going back five generations. For the bad guys, getting somebody on the inside of airport security would be a gold mine, so if you want that job, you'd better have a squeaky-clean record.

Digital Vision./Photodisc/Getty Images
"I killed six terrorists just to get an interview."

Take Jerry Thomas, a 20-year veteran security officer at Newark Liberty International Airport. He was a model employee who had risen in the ranks to become a supervisor in charge of 30 other guards. And he was still a supervisor when he was arrested for identity fraud.

Yes, it turns out that Thomas' real name is (the considerably more spectacular) Bimbo Olumuyiwa Oyewole. The real Jerry Thomas was murdered in 1992, the same year that Oyewole stole his identity and -- like a really boring version of Don Draper -- began working as a security guard in Newark.

Thinkstock Images/Comstock/Getty Images
Fewer affairs, but way more accidentally touching someone else's sex toys.

Now, you may be asking yourself why a company that employs security guards at sensitive installations like airports wouldn't perform a background check. Oyewole may have been hired pre-9/11, but surely there were checks in place that at a bare minimum would turn up someone, oh, using the identity of a murdered guy. It's not like the concept of doing bad things to airplanes was invented in 2001.

AFP/Stringer/Getty
Al-Qaida just hit it big. These guys have hated airplanes since before it was cool.

Well, a background check was in fact performed by FJC Security Services prior to Oyewole being hired, a check that depended almost entirely on fingerprint identification. Since neither Oyewole nor Thomas had ever been fingerprinted before, it was assumed that everything was copacetic. Oyewole also aced state and federal background checks, all of which gave him gold stars for totally not being a Nigerian guy named Bimbo who sneaked into the U.S. in 1989.

And let's not chalk up Oyewole's arrest to additional security measures put in place after 9/11, seeing as how he wasn't exposed until 2012, and then only because someone phoned in an anonymous tip.

AMY NEWMAN / STAFF PHOTOGRAPHER
That dude's detective badge looks embarrassed.

Just by virtue of being a cherubic li'l guy, Corcoran was able to waltz past five security checkpoints and board a flight bound for Rome. He later bragged, "Getting on the plane was easier than doing my homework. I didn't have anything on me and no one asked me for anything. They smiled at me when I went through." Either this kid is the next incarnation of Harry Potter, or Manchester Airport's holographic security staffers (yes, this is a real thing) have been drinking intoxicating photons on the job.

Man Airport Group
It's a British airport. Sober workers wouldn't be authentic.

Mind you, Corocoran was only detected when he began joking to fellow passengers about how much fun it was to run away from home. If there's a silver lining to this entire scenario, it's that the plot of Home Alone 2 totally came true.

An airline might lose your bags now and then, but you can be damn sure that at any given moment they know where you are. The airport is a series of sealed areas that you can't enter without ID, and they make sure that you keep your ass planted in your designated seat for the duration of the flight, barring bathroom emergencies. Which is why it has to be so disheartening when passengers fall asleep during a flight only to have the flight crew just abandon them.

Digital Vision./Photodisc/Getty Images
But if he'd been a cellphone in use during takeoff, you can be sure they'd have caught him.

For instance, in 2010, passenger Kris Lines fell asleep on a flight from Calgary to Vancouver and didn't wake up when the plane landed. Anyone who has flown on an airplane knows that it is virtually impossible to sleep through the deplaning process. There are ding-dings beeping from the ceiling, the captain's voice hyuk-ing over the PA at ear-bleeding volumes, and the general cacophony of a winged metal cylinder defying the natural order. Still, he managed to do it, and the crew just ... left him there. He didn't wake up until an hour and a half later, suddenly on a dark, empty plane, being roused by the ground crew.

But Lines got off easy. In 2010, Ginger McGuire fell asleep on a one-hour trip from Dulles, Virginia, to Philadelphia, only to wake up three hours after the plane had landed to find herself locked inside it.

AP via Telegraph
In this dramatic re-creation, McGuire shows us what it looks like when she sleeps.

McGuire had her cellphone with her, but she only used it to check the time -- 4:00 a.m. -- and didn't think to use it to call for help (a cleaning crew eventually rescued her).

We don't know what's weirder: the fact that McGuire didn't immediately call up emergency services, or that the crew somehow lost her inside a tiny 50-seat regional jet. What'd she do, build a "slumber fort" under a pile of SkyMall catalogs?

Yet, in February 2013, a team of eight gunmen made off with a cache of $50 million in diamonds from the tarmac of Brussels Airport, all without shooting anyone or even having anyone really take notice of what they were doing.

Julien Warnand/European Pressphoto Agency
The fence was actually drunk on duty that night.

How is that even possible? Well, the men were equipped with police officer disguises, machine guns, and a knowledge of the precious few minutes that the diamonds would be unguarded. OK, but how did they even make it that far in the first place? Sure, we had a drunken guy earlier who climbed over a fence at JFK, but this is a group of eight gunmen in a van.

Yep, it's still not that hard, it turns out -- the thieves cut a gap in the security fence large enough to drive their van through, drove up to the jet, collected the diamonds from the hold of a plane, and then peeled off through the same hole. That's it. If this were the plot of Ocean's 14, the movie would be over by the time Carl Reiner's name popped up in the opening credits. So yeah, these crooks (who are still at large, by the way) relied on the exact same tactic you used to sneak into concerts as a kid. But their prize was a $50 million payday, instead of a gripping double bill of Lifehouse and the Baha Men.

Guardian Graphics
We didn't think a plan could be too stupid to fail, yet here it is.

In 2010, Slovakian border police head Tibor Mako instructed his staff to attach two caches of plastic explosives to a single piece of luggage traveling from Poprad, Slovakia, to Dublin, Ireland. Not their own luggage, either -- the luggage's owner was oblivious to the fact that he'd been drafted into this security test. A sniffer dog discovered one of these caches, but the police officer inspecting the bag somehow failed to notice the second.

That's bad, but it gets worse. When officials realized their mistake, they informed the pilot that the explosives were in the plane's cargo ... at which point he took off anyway.

Digital Vision./Digital Vision/Getty Images
"If those explosives were dangerous, someone would have warned me."

The pilot assumed that, because the 85 grams of plastic explosives lacked detonators, everything would be hunky-dory, right? Nope, the entire situation was still the most royal of fuckups. You see, it took Slovakian officials three days to inform Ireland about the lost explosives. When Irish officials learned of this pop quiz gone awry, they briefly detained the passenger -- a 49-year-old electrician, who still had no clue what the hell was going on -- and evacuated a city intersection and several apartment buildings to remove the passenger's new souvenir.

Unsurprisingly, Mako resigned after this escapade. And if there's a silver lining to this story, it's that nobody totally lost the plastic explosives. This is the opposite of what happened in 2004, when Parisian airport security ran the exact same drill and inadvertently gave an unknown passenger somewhere in the world a free pack of detonatorless explosives, courtesy of Charles de Gaulle Airport.

Comstock/Comstock/Getty Images
"And I didn't get them anything."

For more ways people have boned up on the job, check out The 5 Most Hilarious Ways Anyone Ever Failed at Their Job and The 7 Most Impressively Lazy Employees of All-Time.