Rules are made by the powerful. In most games, if the DM has all the power, then the DM decides what all the rules are and those are the breaks. From my own past, I know this is the way most games work. Hell, I've said as much about my world since initiating this blog - so it would be hypocrisy to claim that I don't, in the final analysis, make the rules.
Of course, I've argued many times in the past that the rules I make are intended to produce the best experience for the most players, but that's not relevant to this post. Where it comes to authority, the DM has to step up and take responsibility for the game. I've played in games where the DM did not and I suspect many readers have also had that experience. A weak, spineless DM that makes too many concessions to players that wheedle or fabricate their way through situations is a bad scene. I took part in a game last year with a DM like this and I did not return to play another night.
Conversely, there are many games where the DM grabs too much authority. Hell, the authority is there for the taking. It doesn't take long for a good DM to realize the players are so enjoying the game that they'll submit to greater control. This can get out of hand, but most of the time DMs inherently understand that there's just so far they can go before the players start quitting. The balance between 'fair' and 'insulting' usually translates as a DM that plays with an 'iron fist,' something that isn't expressly enjoyed by the players but at the same time tolerated.
Because role-playing experience begins for most participants during late adolescence, the patterns for what will be tolerated are firmly in place before the players reach adulthood. Since control is harder for a teenage DM, who has little other experience with authority except in submission towards it, that young pattern that is set tends to be on the side of tyrannical. This is, after all, the sort of relationship teens have with their parents and teachers - that is naturally reflected in the DM wielding dominion over their players.
By the times a player or a DM has ten years of experience, the theory of the iron hand is fixed. Generally, it's supposed you have to have one. That in turn produces a response that is also presumed to be fundamentally part of role-play.
Tricksterism has long been a tool used by the weak or the vulnerable to oppose authority through means of connivance, charlatanism or even feigned ignorance, any or all of which serves to disrupt authority or privilege when encountered. Within literature, the servant character (Iago in Shakespeare's Othello or Strobilus from Plautus' Aulularia) is depicted as both servile to the master and at the same time far more clever, turning the situation either for evil or for good in the servant's favour. In Harriet Beecher Stowe's Uncle Tom's Cabin, the black slaves feign stupidity and ignorance in order to disrupt the pursuit of Eliza after she's escaped, knowing they will suffer little punishment as the white slaver's belief system expects black slaves to be ignorant.
Tricksterism works. It is difficult for authority to manage a situation if the participants refuse to participate in anything but the most passing manner - actors that willfully forget their lines in order to confuse or humiliate their peers, cooks who reduce the quality of food in order to encourage hated servers to quit, workers who put off something that should have been done today for contrived reasons, players who deliberately tell jokes in order to suspend play another few seconds . . . these are all methods of undermining authority.
The key to tricksterism's success is that it is easily denied. "No, I didn't mean to forget." "I'm just tired." "I'm sorry, I just had the joke in my head and I couldn't resist telling it." Etcetera. Moreover, much tricksterism originates on a subconscious level. We naturally resist situations or instances that bring us discomfort, so that the uniform we forgot to bring to our hated job wasn't forgotten 'deliberately.' This psychological reality has compelled many a boss to point out that the uniform wasn't remembered deliberately either, so that we are judged not for what we have done, but for what we did not plan to do.
The greater the authority at the gaming table, the more likely there will be a certain degree of tricksterism present. Some of this, yes, will lack malevolence - but a great deal of it will be habitual, in that it was a standard behaviour developed by the player in their youth when dealing with overly authoritarian teenage DMs. We must remember that tricksterism RULES the average high school class, to the point where teachers sit through endless classroom management training sessions in order to master it. We all learn to avoid, undermine and derail authority long before we reach 13. Tricksterism is the primarily curriculum of the modern education system.
Thus we get the myth that part of the game's structure is to 'play the DM' - words I have preached myself in the past. Bigger than that, however, are players who feel the goal is to 'break the DM' - by a number of means that I identify with 'acting out' - as a 10-year-old deciding to wake up the class with a fake epileptic seizure in the aisle on their first day in a new school.
The greater your perceived authority as a DM, the more likely you will find your game disrupted by a trickster. 'Perceived' because it does not matter if you are an iron fisted DM, so long as the player thinks you are one. This is why some players will really try to push the envelope in their first few sessions with you - particularly if you're seen as serious or preoccupied with the game rather than with socializing. The more serious you are, the bigger the target you present.
You should, therefore, be aware of some things. If you're encountering a great deal of tricksterism from your players, it may be that your game has become too authoritarian. If you are a player noting this behaviour in someone else, it may be that they're not willing to put up with the sort of tyranny that you're willing to accept from your DM. It may happen that the player has already learned the habit of tricksterism from some other DM or campaign where this was part and parcel with the way that game was run. Some DMs see tricksterism as a two-way street, so that all the participants approach the campaign with a continuous attitude of one-upmanship, derailment or obfuscation.
There are some who will willfully condone tricksterism, will even say that this is how the game ought to be player. Remember that this is an attitude these people learned while they were quite young - that they haven't yet lost as they've matured.
As a DM, you need to recognize tricksterism for what it is - and reduce your authority while encouraging the player to feel safe in communicating their feelings in words rather than in actions. As a player, you need to recognize these behaviours in yourself - and relate them honestly to how your DM is treating you or how you perceive that you are being treated.
Most of all, everyone needs to realize that tricksterism is a reaction to a problem - not the problem itself. Participants get used to applying to tricksterism as a technique to manage feelings of oppression. The oppression is the problem - even when the feeling is brought from someone else's campaign to this one. Very often, even when freed from oppression, oppressed people will continue to behave as though the oppression is ongoing. Those feelings need to be rooted out, discussed openly and resolved, if a good campaign is to be enjoyed by all.