What would be some funny ways for PCs to die?:   
(The PCs are on a bridge above a bottomless pit, all but a barbarian have crossed.)

Warlock: "Come on!"

Barbarian: "I'm coming!"

DM: Oops, you fell through the bridge. Sorry, your out of the game.

Barbarian: (OOC) Oh, come on!

I'm not sure about funny, but something your example brought to mind occurred some years ago at a convention.

This was a group of first level characters on what was meant to be a 2-3 hour one-shot adventure.   Some ten minutes into the session, while crossing a rickety bridge the cleric slipped and fell.  The paladin immediately turned to the character next to her and said "Here. Hold this."  handing him what the player stated was the end of a 50' rope.  The paladin then leapt off the bridge in a swan dive in attempt to save the cleric.  The DM was speechless. The players all looked at one another. Then the one with the rope said. "Ummm...." and trailed off.  His character was a halfling.  There was a moment of silence followed by various comments about the physics of the situation including the speed of a falling object and the relative ratios of mass between of a fully armored human in platemail vs even the strongest of halflings.    "But," protested the paladin's player, who was fairly young and new to the game, "I tried to save someone. I'm supposed to be heroic."   We all agreed that this was definitely in the spirit of a paladin to rush to the rescue, and spent a half hour or so chatting and telling stories, while the DM set up a different encounter.  

Personally, I am not in favor of any situation that can be reduced to a "Save-or-Die" and I would try to avoid these type of scenarios when running.  In your example it sounds as though the barbarian dies due to a single failed Acrobatic (Dexterity) check.  Most players will likely find this frustrating and possibly unfair.  Why is the party crossing a bottomless pit without taking any precautions?  Admittedly, some groups might favor this sort of "old-school" or "killer dungeon" type of play, I find that most of those with whom I have played would rather have a good story.

So... a good/ funny story death?  

Near the end of a campaign, the characters are in a confrontation with the avatar of an evil goddess. Her cultists have been defeated, but if she can persuade one of them to complete her ritual, she can still return to the mortal realm.  Most of the party members have refused, but the rogue is hesitant, clearly swayed by promises of wealth and power.  

"But," says Robin reluctantly, "even you can't give me what I really want."  

"Oh? What is it that you want?" asks the avatar.

"Ashlyn's heart." replies the rogue, referring to a secret and long held crush she has for the party's sorcerer.  

The being smiles cruelly and extends her left hand towards the rogue.  Clutched in her fingers is a bloody, muscular organ about the size of a fist.  All watch stunned as the sorcerer gasps and collapses to the ground.

[OOC The DM and players all start laughing.  The sorcerer was my character and I think was laughing harder than anyone at the table. That was my most memorable character death.]

Moral: Don't piss-off an evil goddess.

Quote from Eriniel >>

Personally, I am not in favor of any situation that can be reduced to a "Save-or-Die" and I would try to avoid these type of scenarios when running.  In your example it sounds as though the barbarian dies due to a single failed Acrobatic (Dexterity) check.  Most players will likely find this frustrating and possibly unfair.  Why is the party crossing a bottomless pit without taking any precautions?  Admittedly, some groups might favor this sort of "old-school" or "killer dungeon" type of play, I find that most of those with whom I have played would rather have a good story.

 Well, this was an excerpt from a campaign I was playing with this DM who occasionally did something to torture the party; Made up of a warlock (me), a barbarian, a cleric, and a fighter. It was a homebrew campaign where the party was searching for this idol hidden somewhere in this kingdom.

We located the idol deep within a mountain, it was surrounded by the pit mentioned in the excerpt, and the only way across was that bridge. So, there we were.

My hobgoblin wizard has the worst luck. The first time I got to play him in an actual battle, the party was trying to infiltrate a drow fortress. My wiz, since he doesn't haven't the greatest physical stats, used Fly to be able to get over the fort's palisade. So, he was hovering about 60 ft over this fence, and he lobbed a fireball and blasted a bunch of drow. Then the drow peppered him with crossbow bolts, and he failed both the Con save to keep up Fly and to not be poisoned. My wizard fell down 60 feet, smacked his privates against the fence and fell down onto the side of the fence with the drow, and then he got pumped full of bolts next round. Fortunately he got rezzed later, but man death by nutshot was funny.

Here’s a couple that actually happened in games I’ve run...

The halfling barbarian climbed into the dragon’s back before it could take off. As it rose higher and higher, trying to throw him off, he hacked at it again and again...until the players realized what would happen. The looks on their faces! The halfling slew a dragon that day, then plummeted 300 feet to his death, still clutching his foe’s body.

The characters were trapped at the top of a wizards’ college tower, with the artifact they were trying to steal and an angry suit of animated armor. The opportunistic goblin just grabbed the artifact and leapt across the rooftops, deserting the others. Fighting off the armor, they eventually gave chase, leaping across one by one in a scene straight out of a movie...except Rengol, the Gollum-inspired halfling. He rolled a 2 on Athletics.

So, moral of the story, there’s just something about halflings falling to their deaths.

Alright, lets see...

The first character death I witnessed was a friend's halfling warlock, who was climbing the outside of the tower. Dex save failed as they were high up, and they fell. Now, our wizard knew. feather fall -- buuuuuuuuuuut the warlock had cast invisibility to sneak up on the enemies. Needless to say, a third level character could not survive such fall damage. There really is a halfling death-fall-curse.

There was another time our changeling druid fell for the oldest trick in the book. Seeing a chest while infiltrating enemy territory, they started roasting the chest with fire spells because of mimics. Thats when they heard a child crying, and they stopped for a moment. Then a SINGLE kenku jumped out and mauled the already wounded 4TH level character. To unconciousness. The rest of us were too busy trying to fake out the [redacted] guards.

So, I was DMing a campaign in the underdark, and our human fighter was trying to convince this one really annoying gnome to give him a spell stone. The gnome refused to give him the spell stone, so the guy got angry and tried to kill the gnome. The gnome escaped, and then used the spell stone to cast lightning bolt. As this fighter was pretty high level, the spell didn’t kill him, but it lowered his hit points pretty significantly. The whole thing just made this guy even angrier, so he charged at the gnome, waving his sword and yelling. The gnome didn’t like it, but there wasn’t much he could do. The gnome died. His body, however, fell against a “rocktopus” camouflaged against the wall that shot out a bunch of tentacles and ate both the fighter and the gnome.

the moral: Don’t kill random gnomes. Or maybe, never touch cave walls.

This didn’t happen in D&D, but one time in a Vampire the Masquerade game we were all fighting with each other really bad cause of OOC stuff and the DM gets frustrated and goes “Caine (the First Vampire) jumps out of the darkness and eats you all. Game over.”

Quote from PenelopeTheWeaver >>

This didn’t happen in D&D, but one time in a Vampire the Masquerade game we were all fighting with each other really bad cause of OOC stuff and the DM gets frustrated and goes “Caine (the First Vampire) jumps out of the darkness and eats you all. Game over.”

 Insert the DM has had enough of your **** meme.🤣

😂😂😂😂

Two of us liked the same guy irl and everybody else took sides and the DM was a guy too so he didn’t really give a **** either way just was annoyed with all the fighting disrupting the chronicle (that’s what they call campaigns in Vampire the Masquerade).

Lost Mine of Phabdelver Cragmaw Hideout...

Player 1: (Shows a bugbear head to wolves, is a druid)

Wolves: kill player

Other players: trying to go down the fissure

Quote from Jayden0 >>

Lost Mine of Phabdelver Cragmaw Hideout...

Player 1: (Shows a bugbear head to wolves, is a druid)

Wolves: kill player

Other players: trying to go down the fissure

 

 And the moral; Don't show your kills to animals.

Not a death, but close...

Player 3: *making death saves*
Other players: *decide to keep fighting the weak enemies instead of stabilizing Player 3*
Player 3 on each player's turn: *starts making noisy death rattles*
DM: Can you die more quietly, please?

(Player 3 survived, though, almost had to roll one more death save which could have killed the player because Player 2 Artificer couldn't decide what tool to use to cast healing magic and the DM wanted to move things along. Player 2 ended up using a bucket of water. Somehow so weird and strangely appropriate at the same time.)

bottle on a table. low level Brute rolls a 1 on Intelligence check. Drinks it. Turns out to be purple worm poison. You know the rest.

I wasn't in this campaign, but here's the story. Two parties, questing for the Hand of Vecna, one party gets the Hand, but they also leave clues and trails to a "Head" of Vecna, and as the other party follows the trail, they don't realize it's a trick until two of their party members have died.

Quote from RangerTwoBlades >>

I wasn't in this campaign, but here's the story. Two parties, questing for the Hand of Vecna, one party gets the Hand, but they also leave clues and trails to a "Head" of Vecna, and as the other party follows the trail, they don't realize it's a trick until two of their party members have died.

 I heard that story from my old DM!

Quote from The_Hive_Mind_704 >>

My friend was severely injured, and they died to a spider. Not a Giant Spider, but a challenge 0 tiny spider. 

 😂😂😂

Wow. I...... Might make a wizard style character just to summon a spider to kill my friends......

Quote from PenelopeTheWeaver >>

Quote from RangerTwoBlades >>

I wasn't in this campaign, but here's the story. Two parties, questing for the Hand of Vecna, one party gets the Hand, but they also leave clues and trails to a "Head" of Vecna, and as the other party follows the trail, they don't realize it's a trick until two of their party members have died.

 I heard that story from my old DM!

And I heard it from my dad, who probably heard it from HIS DM. And, I also saw it as a comment on a Video from Rocks Fall (Everyone Dies) On Youtube.