Calvin: [writing] Yakka foob mog. Grug pubbawup zink wattoom gazork. Chumble spuzz. [aside] I love loopholes.
Someone — typically a Rules Lawyer — does something outrageous by finding a loophole in the rules, which were too narrowly written to consider such possibilities. This allows the agent to get their way while claiming they were technically following the rules.
Sometimes the loophole doesn't really exist, but the competitor is convinced it does based on his own misinterpretation of the rules. If the loophole's existence is explained, one justification sometimes is that when the rule was designed, the Loophole Abuse seemed absurd enough that no one would ever be stupid enough to try it. This is a form of Refuge in Audacity. The Comically Wordy Contract will often contain these, especially if a Deal with the Devil is involved.
In games, this may often be the result of some kind of oversight by the creators. A programming oversight can cause someone to do something they did not intend, such as killing a mob intended to be invincible.
In Real Life, this is more difficult for two simple reasons: First, loopholes are quickly closed once discovered, sometimes by an Obvious Rule Patch. Second, many systems have Rule Zero: some designated referee, judge or authority figure has the absolute final word and can simply throw the argument out wholesale, usually by claiming that the "spirit" of the rule never intended to allow what the "letter" of it seems to say. On the other hand, some "loopholes" were actually exceptions put in the rule for a reason and as such are (or have become) part of the rule.
Also note that before you add an example here (especially under Real Life), loopholes are different than exemptions and provisions. These two are intentional exceptions to the simplified version of a law. For example if a government taxes pools and a pool manufacturer starts manufacturing large hot tubs to get around it, that's a loophole. If that same government decides they don't want to tax hot tubs, they will add a provision that says hot tubs are not pools. The former pool manufacturer is now using a provision to manufacture hot tubs and is following both the letter and spirit of the rules but this may not be readily obvious to an outside observer.
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- This Segata Sanshiro commercial. Apparently there's no rule against grabbing a guy off the sideline and hurling him at the ball to score a goal for your team. Subverted when the referee gives Segata a red card.
- In the Spock vs Spock Audi commercial, Zachary Quinto and Leonard Nimoy have a race to the golf course and the loser buys lunch. ZQ in his Audi wins the race but as Nimoy points out "Technically we're not inside yet" and subdues him with a Vulcan neck pinch.
- Underoos brand underwear first got around the de facto taboo about showing a bunch of kids gallivanting in their underwear on TV by calling their product "costumes" instead of underwear.
- Hasbro commissioned Marvel Comics to create a G.I. Joe: A Real American Hero Comic Book and advertised it on TV for a special reason. Namely, animation featuring a toy on a TV commercial is strictly regulated, but the regulations were much laxer for an advertisement on a literary work. Thus the advertisements could feature their toys in full animation because it is officially the comic book itself that is being advertised.
- In Sweden, it was once illegal for domestically-run commercial broadcasters to air commercial breaks during programs; they could only do it between programs. So what did TV4 (an OTA network which, unlike its cable-based competitors who broadcast from outside the country, was subject to said rules) do? They split a program with an interstitial, thus allowing them to air ads "between" programs.
- The famous Apple MacIntosh 1984 Commercial is often stated to have only aired once, during the 1984 Super Bowl on Jan. 22 1984. However in order to qualify for the prominent Clio Awards it had to air at least once in 1983 so they purchased time to run it on a small station in Twin Falls, Idaho shortly before midnight on Dec. 31 1983. It was likely only seen by a few hundred people at most. This was way before social media could spoil it so the result was the ad made its impact and is often regarded as the Greatest TV Commercial ever.
- A couple from Mission To Zyxx:
- As a diplomatic mission, the crew do not have clearance to carry weapons of any kind. Dar's ion blaster is thus filed as spare droid parts, since it was originally part of a destroyed droid.
- Nermut attempts to negotiate a nonaggression contract with the tornada (one of his race's traditional predators). When it claws the bottom line in a struggle, he successfully argues that the claw mark constitutes a signature (like an illiterate person's mark) and enforces the binding contract.
- In Higurashi: When They Cry's backstory, citizens of Hinamizawa protested the construction of a dam that would flood their town by, among other things, chanting Buddhist sutras at an extremely high volume outside the construction site so their protest would qualify as a religious service, and therefore protected speech, and the police would be forbidden from doing anything to stop them.
- The Original Ace managed to bypass demonetization by copyright claiming his own video... What an absolute madlad.
- Tool-Assisted Speedrun website TASVideos often uploads runs that beat the game in a ridiculously low amount of time. The catch is that "beat the game" is defined as "trigger the The End screen", even if that's done by exploiting an obscure glitch rather than, you know, beating the game. A few egregious examples jump into the ending sequence from the middle of the game for no apparent reason.
- Weird school rules in Hong Kong: The students often take advantage of the wording in their ridiculous school rules to bend them to their advantage, especially in the face of the more obstinate teachers. How well this goes tends to depend on the skit.
- In Episode 1, in the skit discussing a rule against wearing leather shoes to school, the student explains that his shoes were "made in [the Strong Country, i.e. China]" and therefore didn't contain real leather. We don't know if the teacher accepted this as an excuse, though.
- In Episode 2, in the skit discussing a rule that only permits glasses with black frames, a student lends his 3D glasses to a schoolmate, Yan-yan (whose glasses frames violated the rules), because his 3D glasses had purely black frames and didn't violate the rules.
Male student: What's going on?
Yan-yan: Ah Sir said we can't wear glasses that don't have black frames.
Male student: So, ah Sir, we can only wear glasses with pure black frames?
Teacher: (smugly) Of course—if they have pure black frames like mine, you can wear them.
Male student: Yan-yan, you can wear this pair of mine. (takes out a pair of 3D glasses with pure black frames and hands them to Yan-yan)
(Yan-yan takes the 3D glasses and superimposes them over her own glasses with black and brown frames, smiling)
Teacher: Huh?! Even 3D glasses for watching movies?!
Male student: Ah Sir, how can you take back your words? These are glasses with black frames!