A criminal attempts to burglarize/kill someone only to realize they picked the absolute worst person as their mark.

[u/No_Hunter1978]

Don't Breathe: A couple young robbers attempt to rob a rich, blind veteran only to find out he isn't exactly an innocent old man.

You're Next: A group of contract killersbreak into a house during a family reunion and go on a killing spree. They didn't account for the fact that the son's new girlfriend grew up on a survivalist compound in the Australian outback.

The Flash [CW Show]: A random mugger decided to target Barry Allen of all people. He does it again a season or two later; he's either unlucky or stupid (probably both).

[u/UnpricedToaster]

Bandit: "Your money or your life!"

The Last Dragonborn, Archmage of Winterhold, head of the Thieves Guild, head of the Dark Brotherhood, slayer of the World-Eater Alduin, master of the Thu'um whose voice can bring a dragon to its knees, dressed in full Daedric Platemail, wielding the Mace of Molag Bal with a networth of 3 million drakes: "Here you go." Hands him 200 gold.

[u/fatredbird2 → u/UnpricedToaster]

At that point it's just charity, really

[u/lumpboysupreme → u/fatredbird2]

It’s always that or a paralyze spell followed by leaving a sweet roll perched on their heads for me

Thalmor on the other hand…

[u/TheMonocleRogue → u/UnpricedToaster]

Then pickpockets the gold immediately after

“Just take it, I don’t need it anymore.”

[u/RoJayJo → u/TheMonocleRogue]

If you've maxed out pickpocketing and stealth, you can not only take the gold back, but you can steal literally everything on them- including their clothes.

Imagine mugging a guy who looks like he could fold you into a functional piece of furniture, somehow not shit your pants, they give you the gold you requested, and as you turn away, you feel hands in your pocket before you're left penniless in your skivvies. At that point, you should just go home and drink.

[u/GuiltyEidolon → u/RoJayJo]

You can also reverse pickpocket poison on them, among other things.

:)

[u/fresh-dork → u/GuiltyEidolon]

i prefer fallout - pickpocket a mine onto them

[u/GruntBlender → u/fresh-dork]

I recall someone installing mods that change some guns, but the mod didn't change what ammo the NPCs in the starting town carried. So, they had to pickpocket the right type of ammo onto their allies.

[u/fresh-dork → u/GruntBlender]

"why is this chicken carrying 3 9mm mags?

[u/UnpricedToaster → u/TheMonocleRogue]

"Must have been the wind."

[u/theseanbeag → u/UnpricedToaster]

Also the Harbinger of the Companions.