i'd probably have to say the time a friend, who recently back from semi-serious dental work that required what was apparently massive amounts of local anesthetic, showed up unexpectedly and decided he'd take a very active role in a frankenstein v. villager type negotiation. his girlfriend drove him over because he insisted that he play. anyhow, insofar as the negotiations, nobody realized that the lead "villager" speaking out against the monster was actually a cultist-plant, hoping to incite the villagers into lynching the monster. the monster, although rough-looking, was actually neutral and just wanted to leave. i think it was a half-dragon hagspawn, but i'm not sure.
nonetheless, these are my fondest memories, as the DM running the encounter:
1) said character forcibly imposes himself as the grand arbiter of the negotiations, telling the party's charisma 20 diplomancer-bard to step down. bard steps aside and informs me he'll ready an action to jump in as soon as it seems needed. surprisingly, it wasn't.
2) said character uses a "tree token" to make a massive oak tree, so he can stand on it and impress the locals.
3) said character loudly tells allies that the tree token is to impress the stupid locals into taking their side. when i told him he probably shouldn't announce that in front of everyone, locals included, he said he didn't care because trees are awesome and "...nobody effs with warlocks!"
4) said character explains that he's going to scream that the lead villager (actually the secret bad guy) is a "super horse molester". we laugh and he proceeds to roll a perfect 20. the sputtering cultist tries to counter-argue and point out the foolishness of the warlock, and of course rolls a natural 1. even with modifications, he beats the bad guy's opposed DC by like 16 points.
5) warlock announces that every time the other guy speaks, he's just going to scream "super horse molestor!" over his arguments. he then proceeds to roll a series of DCs that, i kid you not, never go below 17, while the bad guy can't seem to ever get above a 9.
6) after a short time, the crowd now is no longer concerned with the monster, who is standing there bewildered. said warlock continues with one of the most surreal debates of all time. crowd is now concerned for the safety of their horses and begins to turn on a very confused hidden cultist.
7) at the end of the debate, which saw the monster free to go and the secret bad guy imprisoned for "horse endangerment and molestery", warlock steps down from tree, and falls 40 feet, taking like 15 damage in full view of everyone. he tells me he gets up, bows and dusts off and tells the locals to enjoy their new tree. he also later explained that the locals - who he viciously insulted at almost every turn - were probably so impressed that he didn't die, that they should make him the mayor.
it was hands down the silliest two hours that we played. for reference, it was a little like this, except with a 23 year old playing a warlock: [ame="http://www.youtube.com/watch?v=txqiwrbYGrs"]YouTube - David After Dentist[/ame]
