Scope
This document exists to make the reader aware of the basic principles of conversational derailment. This document will focus on non-real time internet communications such as message boards and blogs, but many of the practices learned can be leveraged in real time communication as well as in your daily life. Trolling is a concept that is usually associated with the internet, but can thrive in any environment where stupidity is the norm (such as management staff meetings).
What is derailment?
Derailment is the most absolute form of rebuttal. When you begin a derailment you are taking on the mark in a battle of cunning. Winning a derailment is completely dependant on winning over the observers, it is a game where wit and intellect take the backseat to charm and style.
Think of derailment as a way of winning threads without actually making a coherent argument.
Derailment and Trolling
Many of you are familiar with trolling and have deduced that derailing and trolling are the same thing. This is somewhat true, but not fully. Derailment and trolling are both about the manipulation of people to incite a response in the name of comedy, but their goals are different. Derailment intends to cease a discussion in order to shut the mark up, and trolling intends to drag out the argument as long as possible to make the mark look like an ass. However, making the mark look like an ass is a great way to ensure that a derailment goes your way. Trolling can and should be used as a tool in derailment, as we will see later on. Troll->Derail->Win.
Taxonomy
In any thread that you are trying to derail, every poster in that thread (other than you, of course) is one of the following: Mark (the person that you're trying to derail), Preposters, Dissenters, or Eggers.
Preposters are the people who post between your Mark's post and your reply, who's posts are relevant to the discussion. In most cases, you must derail all the Preposters as well as the mark. People who spout retarded offtopic bullshit can be ignored, or are perfect candidates for eggers.
Dissenters are people who are trying to covertly or overtly stop you from derailing. They either are arguing against you, not buying in to your derailment, or are overtly announcing that you are trolling and trying to derail the thread.
Eggers are your most important asset. It's cool to derail threads, and once you start, a handful of people will try to derail the thread with you. Unless you're derailing anonymously, they are almost always the same people time after time. Eggers are hard to manage, especially if you also post seriously, because you will have a few cronies that follow you around in every thread. It's import that no matter how much shit you have to put up with (see: Ariannda's posting history), you cannot lose these eggers, or your derailing times are over(for that message board).
It is important to note that, should someone else be trying to derail the same thread that you are, treat them exactly like an egger.
Anonymity
Derailment can either be done anonymously, that is, with an account that the majority of the forums population have not seen before, or nonymously, with an account that they are familiar with. Anonymous derailment is very hard to pull off. Low post counts may be a signal that you're trolling, but the biggest factor here is rapport. You need the general forums population to be on your side before you even start trying to derail. If they don't think that you actually won the thread and are trying to derail it, they will think you are an ass and are trying to cop out of an argument.
Note that one can still derail with rapport by using several fake accounts, as long as they each have a decent sized posting history. There are many pitfalls that can trap you when using multiple accounts (IP checking admins, the page 8 problem, etc), and they are out of the scope of this document to try to enumerate. A good rule of thumb is that you shouldn't use two accounts in one thread.
Overt vs Covert derailing
Derailing can either be overt or covert. Overt derailing involves laying the cards right out on the table, stopping just short of saying "I claim this thread." Covert derailing is much more subtle, and trolling must be used to turn the thread to your favor before claiming it.
Overt derailing will attempt to derail the thread in one post and subsequent following posts, covert derailing will lead the thread in the direction of derailment (usually ending in a final, overt derailment).
A general rule of thumb is that, if you judge you and your eggers have enough rapport (in comparison to the mark) with the community to win the thread without an argument, derail overtly. If you think that a little chicanery needs to be used to win favor, derail covertly.
Overt derailment is used when you know you have enough eggers to win, and covert derailment is used to turn dissenters into eggers
Collaboration
It is sometimes worth while to take preplanned collaboration and make derailment a true joint effort. IMs and conference calls will make it a sure thing that you will win the thread. Account sharing can be used so that you're posting 24/7, be careful though, Karjia and I almost ruined this epic thread (a derailment that was planned days if not weeks in advance) by both posting as Megatron at the same time around page 15 or so.
Overt derailing tactics
The most basic overt derailing tactic is "first post." Thi s is as old as time itself and involves replying to the thread as soon as possible, with only the words "first post." Note, it is not at all necessary to actually have the first post, merely to be within the first ten posts are so. Ideally, your eggers will promptly reply with "second post" and "third post" and so on. If the mark does not feel very passionately about his thread he will give it up right there, but may continue on. Should he reply and ignore your derails, simply reply to his post with "first post".
"what" and "ok" are close cousins to "first post." As one can conclude, these tactics involve quickly replying with "what" or "ok" It is very important that no punctuation or capitalisation be used, the idea here is to show a total lack of effort. If the mark replys, simply reply with "what" or "ok" again, making sure to use the same one that you used before. It is best to pull this off with no preposters. In the case of preposters, you may want to quote the mark when replying, but be careful to not show too much effort (if possible, screw up the vbcode show the quote tags show up but quote doesn't actually work). It is unpredictible what eggers will do in this situation, and you can usually pull it off without their help at all.
"Paragraphs" is a tactic which is used in special scenarios when the mark posts a lengthy dissertation without the use of paragraphs. "Paragraphs, dude" and similar also work, but something like "I simply cannot read this text! Your typography causes pain to my eyes. Please consider using paragraphical notation, for the sake of all of us!" is right out. Remember, low level of effort = more style. Similar tactics are "Cap lock" and "Punctuation" and "Speeling."
The babelfish switcharoo is an absolutely hysterical derailment, and should be used when the mark has trouble making his point clear. Simply run the text of his post through babelfish, translated to a language of your choice, then translate that to another language, a few more times, and then back to english. Quote the result, and say "I just didn't understand what you were saying, so I ran it through babelfish a few times in order to make it more clear."
The concept of image macros have existed for quite a while, and have been made popular by Something Awful. Though they usually reek of stupid in-jokes, one can use relevant image macros to help in an effective derailment. You must find/create a collection of image macros that are relevant to the discussions that you want to derail. An easy target for the beginner derailler is livejournal/myspace/deviantart "cry for help" type posts:
Fig. 1:

It is important that you have a second, more to the point, image in case the mark attempts to recover, in this case I would use (NOTWORKSAFE) this .
Your images have rapport too. Many people here remember downtheroad.gif. In the late part of downtheroad.gif's life, I did not even have to post in threads to get them derailed, eggers would derail them for me by just asking for me to post downtheroad.gif.
Eventually, your images become over used, and should be retired, as is the case with downtheroad.gif.
The Wikipedia is probably the most consistantly successful overt derailment, if it isn't overused. You must not use the Wikipedia on the same message board very often, or you will become a gimmick. The Wikipedia involves googling an article completely unrelated to the subject, posting the entire text of that article, and then hitting submit. Hopefully your eggers will do the same thing. You can do this multiple times if you want. The MySQL manual is always a good choice. There was a legendary thread
Covert derailment
"And then what happened" bridges the gap between overt derailment and covert derailment. Basically, quote the marks post and reply with "and then what happened." You should reword it, use punctuation, show effort here. Whenever the mark responds, quote his post again with another "and then what happened", ad infinitum. You should reword the phrase each time so as to not make it obvious what's going on, and then when you're ready for the thread to be over, use the same wording every time from there on out.
The Alice in Wonderland is another hysterical tactic when used properly. It can only be used on forums which will allow you to control your font size. Simply respond whole heartedly, with great length, and with great passion for the marks post. Then, when it's time to respond again, respond tactfully one font-size smaller. Always be wordy. When you get to round 4 or so, it will be obvious what's going on and a good laugh will be had by all, except the mark. Growing text is almost as funny.
Advanced Covert Derailment
These tactics are called advanced because they require a level of skill to keep up. "And then what happened" and Alice and Wonderland will never be revealed on the first or second post, but these tactics can reveal you if you do them carelessly or misjudge the intelligence level of your audience.
"The Forbidden Hello" is a tactic named after the subject that it is most often about -- anal sex. When arguing/trolling with your mark, simply quote a scientific article, essay, or blog post from elsewhere that backs up your point. Make sure that it's huge, so huge that no one will actually read it. Insert "anal sex" or another similar phrase at some hidden place in the quotation. For example, if the article was about a guy named Greg who had videos, change "Greg's videos" to "Greg's anal sex videos." One occurance is enough. Do this each time you reply, making it more and more obvious. Don't let yourself be revealed until you think you are winning the thread. When they find out that you've been bullshitting them the whole time, the thread will be over.
"Mama's Family" is quite similar to The Forbidden Hello. Simply quote an article in argument, and replace the names of all the people in the article with the names of people from an old or obscure TV show, Movie, or Book. Make it obscure enough that no one will figure it out. Then when you are ready to derail the thread have one of your eggers "notice" it.
"The tangent argument" is where it gets really serious. You have to put your heart and soul into this one, you have to care about it, and you must play this out. Simply respond to the marks discussion with an argument that is on topic, but completely different, and completely overwhelms the marks discussion. The idea is to get everyone else that replies to reply to your argument instead of the marks. Go on as if nothing ever happened. If anyone brings up the mark's topic, tell them that they should take off-topic discussion to another thread.
The Adequacy Style Derail (ASD) is quite possibly the pinnacle of derailing. Many of you are familiar with the Adequacy Style Troll (AST) as a virtuoso display of trolling, those of you are not should read this excellent description of it: http://www.kuro5hin.org/story/2003/7/18/205013/523 . The ASD aims to actually win the argument (even though you know you're wrong, and most of the other people reading do too), beating down your opponent with layers and layers of quotes, citations, and circular logic. Eventually, they will give up. Words and words can be said about the AST and ASD, but the k5 article illustrates it much better than I could.
Successful derailment may involve a blending of one or more tactics. New Derailers should practice on easy targets (such as livejournal or myspace), and work their way up. You must properly evaluate your mark and the forum community before engaging in a derailment, you need to know what kind of responses you will get, what your eggers are likely to do, who your eggers are, before you can determine the correct strategy to create a successful derailment. With lots of practice, anyone can be a good derailler.