Ahhh, the cunning, funny trickster. We love him in movies and books - after all, his literary roots go back to the oldest myths of mankind. A lot of us probably wanted to be him at some point in our lives. Many systems offer special prestige classes or sometimes entire races that cater to the archetype. And yet… the whole table groans once player X announces his “really funny chaotic neutral gnome illusionist who is an incurable prankster!” For some reason, more often than not, this archetype may look fine on paper but seems to translate really badly into actual gameplay.
I’ve encountered several “trickster” PCs over the years and for basically all of them being a trickster just involved playing pranks on fellow party member. Examples include putting slime in other people’s boots, putting the paladins hand in warm water at night (apparently, that can make you wet yourself?) or groping female PCs while invisible. Most of the time, they did this without reason except “Well, my character is a gnome/CN/etc!” Being ‘mischievous’ was seen as some sort of get-out-of-jail-free-card to just be an a[**] to fellow players.
Now, most of this is already covered by “My Guy”-Syndrome. Being ‘in character’ is no excuse for being a pain. But considering how the archetype normally works, MG-Syndrome seems kinda inevitable to me. If we look at the classical trickster, he is almost always defined by his interaction with others – mostly how he cheats/outsmarts them. Even more generally speaking, practical humour almost universally comes at the expense of others. (Ideally, even the victim laughs at the prank, but honestly, how often does that happen?). So, in order for a trickster to work, there need to be ‘the Others’ whom he can trick, dupe, prank, etc and those ‘Others’ tend to be, well, everybody around him. Including the party. And while being the trickster is great fun, being part of ‘the Others’ ... isn’t.
So… could you make a trickster that does not work at the expense of others? Have you seen examples of good tricksters in a game? (For this question, I would love answers from people who've had such a person in the party, not the person playing the trickster themselves.)