One of the players in our game, a new player who doesn't know the rules, is always trying out unconventional actions in combat with her Halfling rogue. I'm not the DM in this game, but the DM often looks to me for rules advice. The player in question's actions are informed by visions of swashbuckling action and include stuff like jumping into barrels for safety and slamming doors into enemy faces. Jumping onto the shoulders of large creatures and stabbing with her shortsword is a favourite. Personally I think this stuff is awesome, she has a great imagination, and to have one player who doesn't simply move to adjacent square and attack with sword really adds to the game. Its hard work tho! You need to not only have a mastery of the rules, but you need to be able to remember them at the right time.
Cinematic color to combat is a very important part of good roleplaying. When players interact with the environment creatively and are sufficiently immersed that they can imagine the environment, that's a good thing.
There are some potential drawbacks:
a) If the stunts become routine, they stop adding a lot of value. You want to avoid having a situation where the player does the same thing over and over again.
b) If the stunts become too zany, they can detract from the atmosphere of the game as much as they add to it. If you aren't going for slap stick comedy, there is a level of 'over the top' that is too far over the top.
c) The player can become stuck either with the impression that no stunt is ever worth it because the DM/system crushes creativity, or else they are always worth it because no matter how hare brained the idea the DM will reward it.
Does anyone else have characters that like to pull off crazy stuff? What's the craziest stuff you or your friends have attempted? How do you as DMs handle these things?
Yeah, I've had those players before.
As a DM, I have a standard bag of tricks for adjudicating things.
The simplest way to ad hoc rule is simply along the lines of, "OK, if you can make a DC X appropriate skill check, you get a +n circumstance bonus to your attack/damage/AC."
The next thing is to translate an creative action into a defined combat maneuver or stance, or in some cases a series of them. For example, is the character effectively fighting defensively in describing the action? I might decide that 'Duck inside a barrel' or 'Slam door on foe', constitutes 'Fighting defensively + a skill check for a small circumstance bonus'. Kicking a chair into a foe might be treated as a 'Trip Attack' with an improvised range weapon - not likely to work maybe, but also you aren't drawing an AoO.
To provide for that, I have a variety of actions I've defined in the rules that are pretty common PC narration. One of them is the opposite of 'Fighting Defensively', 'Fighting offensively', which is typically used whenever the players describe themselves acting in a particularly rash manner. It might be a quite successful attack, but it leaves them wide open to a counter attack or attack of opportunity. So, leaping down off a balcony and trying to drive your sword into an opponent might be resolved as "Charge + Fighting Offensively + a +1 circumstance bonus to attack from attacking from above + Jump check vs DC 10 to gain +1 circumstance bonus to damage." Putting that all together quickly produces a simple set of modifiers to the attack roll along with some fun color without being unbalancing. Leap down far enough, and I might add damage from impact to both the target and jumper, but I'd probably also increase the DC.
One thing you mention that I found occurred a lot was players wanting to climb or mount a large creature and stab it in the back/head/neck. The rules want to treat this as a grapple, but it doesn't really work either mechanically or by intention. A player doing that isn't trying to control the enemies limbs and pin them motionless; he's trying to get inside the enemies guard and attack them in a way that they are relatively defenseless. A mosquito that lands on you isn't 'grappling' you. Something else is going on entirely. This has been generalized to a maneuver called 'Clinch' which is the counterpart of a grapple. In a clinch, the smaller creature is favored over the larger one, though of course, the smaller creature is in danger if the larger one can convert the clinch to a grapple, and the larger creature can perform a thrashing action to crush the pest, and there are several other hazards as well. However, it provides a standardized way to handle something that is a staple of fantasy and player's stunts.
Just off the top of my head, recently in my campaign I've had characters: bull rush zombies off pits, lasso skeletons and drag them into pits, leap on to and over tables to attack, jump down off of roofs to deliver flying charge attacks, burst through roofs by casting enlarge self, somersault between an enemies legs to attack from the rear, shield rush ghouls to prevent them from performing coup de grace attacks, shield fallen friends with their own bodies, lock blades with an undead warrior in order to spin it around and shove it between other party members, and a bunch of other stuff. It's all a blur really for me at this point. I distinctly remember a player pulling of a three skill trick combo, where another player said, "If this works, it's going to be awesome.", and I remember it worked, but for the life of me I can't remember what it was. And the Sidhe rogue has gotten to the point where he can pretty much bounce around spinning like Yoga in the prequels during combat, and pull off pretty much anything he can imagine. But that's not even really creative at this point, it's just the rules.