Please...don't talk to me about 'grapple checks'.

One group I DMed for made me unable to ever look at the 'grapple rules' the same way again.

They're the reason I put everything 'grapple' in quotes just now.

Although, it was interesting making them have to 'grapple' with a sentient doorknob that didn't want to open.

The Ride Skill.

My character got married, and his wife got a special saddle/lingerie with a bonus to the Ride skill.

Yes, it's both as hilarious and weird as it sounds.

Neat, sentient doorknob's....also:
ADAMANTIAM RAGE!!!!!!!!!!

I remember reading this one post somewhere about a guy who made a berserker with a Luchador mask, and he wrestled a DRAGON out of the sky.

And that's how he became level 4.

I believe Los Tiburon was a Monk, actually, not a berserker.

My voice gives me superhuman strength!

As for the topic, gonna tweak the question slightly because it was what grappled what that was strange.

It was a crazy high power "Kitchen Sink" 3e GURPS setting where you had magic, psionics, super powers, etc. running around in what would still have been a higher power fantasy/medieval setting... and most PCs had four digit character point totals. Because I was rarely able to attend, the GM thought we'd have some fun by letting me run an Adversary for the players to beat.


I was at a point where I could only attend sessions irregularly, and in an "anything goes" high point GURPS game I got to run an "Adversary" character... that everyone else just assumed was a PC. I ended up bringing in a super with body manipulation powers (morphing plus some levels of growth, shrinking, and stretching) that had become a nigh-immortal mage in the service to the campaign world's "God of Death". Yes, my point total was ridiculous... but I was up against at least a half dozen PCs and I doubted I could take out more than two by surprise.

I used my shapeshifting powers so that I showed up as a very attractive male character, realized one of the PCs was romantically inclined towards me and we went for a quite walk alone. I had purchased each of my fingers and toes as Strikers, with claws capable of Impaling damage... plus my tongue for good measure. In a romantic embrace, as we went to kiss, I prepared to quite literally tongue stab her.

Would have almost certainly scored a PC kill except that character owed a favor to said djinn who stopped me mid-strike. So a djinn grappled my tongue. @_@

I played a size changing ape-like mutant, who was ICly named for the movie character. While fighting extra dimensional Nazis, to protect civilians, he grappled and lifted a pair of buses over his head, then yelled at the Nazis, "Bad Nosies make Joe hold up traffic, Nice Police Guy McDougal tell Joe holding up traffic is crime... STUPID NOSIES MAKE JOE COMMIT CRIME" then proceed to foot grapple their tank ('Panzerblitzer' or something like that) and fling it... yes... he was grappling with his right foot :)

So I was playing a Pathfinder edition of the Red Hand of Doom as a cleric with some necromatic tendencies and we got a random encounter with a Grey Render. We won, I raised it with the bloody template and it proved to be the most powerful/effective member of our party. We got to a section of the campaign where there was a big bridge that we had to destroy being guarded by a dragon. We screwed up pretty badly, things got desperate, and I got a crazy idea. I moved the Render to the center of the bridge, grappled the dragon, failed the first attempt, succeeded the second. My next move with the render was to jump off the bridge with/pulling the dragon. Not entirely sure if that would have worked but my DM was flabbergasted that I actually managed to grapple the dragon and allowed it. The worst bit was the dragon didn't die, but it fled afterwards. So successfully grappling a dragon and pulling it to its near death in a chasm was my favorite/weirdest grapple.

So, Our DM was running a Pathfinder Campaign in a very high magic setting, and our party was reasonably odd. I was a multi-class Ranger/Rogue, and we had a Dwarven Barbarian and a Halfling Monk.
Well, we were running an errand for the information broker, Lord Wikipedia, and encountered a sentient, angry Gazebo, complete with table and chairs. Our monk couldn't do any damage through the hardness of the building's DR, so once he was done turning the furniture into kindling, he promptly decided to grapple the gazebo. Meanwhile, I was slowly whittling away at the stairs with my adamantine dagger, but just the fact that he actually managed to grapple, and hang onto the gazebo for any length of time was hilarious.

That campaign sounds awesome. He actually referenced the Dread Gazebo, and that makes it awesome.

My group doesn't do much grappling, but I did have one that stands out a bit.

My Exorcist (playing Deathwatch) was having some down time at the Watch Fortress when the local commander (an Ultramarine who hated our Kill Team for making him look bad all the time) challenged him to a sparring match. We went in unarmored and with practice weapons, and he wound up disarming me and leaving me nearly crippled with critical damage. As a last-ditch attempt to win the duel I jumped him and initiated a grapple, and proceeded to beat the crap out of him. I'd have broken his arms and left him crippled and unconscious but he ended the duel early and called it a draw...

I'm running my first campaign. My group is traversing through a booby trapped haunted mansion where everything spits them out of the grounds of said mansion, or scares them into leaving.

In the main room... or greeting room, the chandelier's normal candles had been replaced by fear candles. The light was concentrated through the hanging glass and every turn, everyone had to make a will save to avoid leaving out the front door. This wouldn't have been too much of an issue, if they weren't on the second story and the outside stairs weren't sharp pokey rubble.

The Chandelier and it's chain had their own AC's to hit. The Chandelier was 10 - 19, and the chain was 20+. Not a natural 20, that included bonuses. Outside of that, they'd crack the glass and create more "fear beams" if you will and increasing the Fear Roll they had to beat.

As this "greeting room" had two levels, the dwarf Fighter ran up the stairs, leaped over the balcony and grabbled the Chandelier... then attacked it with his dwarven axe.

The team then tossed a rope up to tie to the Chandelier, and they heave ho'ed the damn thing down. The dwarf made his dex check with a NAT 20 and landed like a boss.

Not exactly the outcome i was expecting, but we all got a huge laugh with a dwarf tossing himself and being a monkey on the Chandelier of terror... all without loosing one bit of badassery!

So this was actually the first campaign I had ever played. The DM was a freshman in highschool (I was a junior and he was the one of the only two people who had ever actually played before). Due to our groups lack of expirience he decided to give us whatever we wanted and an instant 15 levels. I don't remember what class I was running but it was a dwarf who could wear plate armor. The armor I took was spiked full plate. So anyways, we go out to fight some super dangerous lackey and I get disarmed of my war axe. So, I used the only weapon I had left. I hugged a mini boss to death. Needless to say this became a running joke and I would intimidate my way around by spreading my arms wide in a warm, caring, spiky, hug-intended gesture.

Only tangentially related to grappling, but once my druid/Master of Many Forms let himself get eaten by a dire shark so he could Wild Shape into a scrag to give it internal damage. MY calculations were off, though, so I wound up "only" ripping it open from the inside. Then getting shot at by my party members when we realized I had never wild shaped before, period, let alone into a scrag.

Good times.

The moon.

I'm not kidding. It was a very high level epic game.

"grapple with the elementary school teacher" (Best part, she knew her stuff about grapple.)
"grapple with the Owl"
"grapple with the sentient battering Ram."
And finally, "I'm going to grapple Lugia!". Was'nt really Lugia, just a giant white Birdlike thing who could fly high or swim in the abyss, so everyone called it Lugia.

some years ago I had a buddy who made a character with an ability that briefly gave him super hero levels of strength to grab and lift/throw big and heavy stuff.. in exchange for becoming Naruto to Luffy levels of stupid and having to use some form of silly,cheesy or botched quote before he flattens the baddies.

the ones that stuck in my mind were
using a military tank as a club "I love the smell of napalm with two eggs and a side of toast!"

throwing restaurant grill through a window "Order up in the court!"