Top Definition
An adjective to describe the attribute of chaotic beauty. Used only in sentences describing a person, place, thing, or event that exists or is created haphazardly, dangerously, yet brilliantly in a fashion that works better, looks better, and is generally more successful than anything that meets the standards of society.
Example 1

Person 1: How can we make this backpacking trip as jackshaw as possible?
Person 2: We stop thinking and go.

Person 1: I don't know if we should cross that bridge man, half of the planks are falling off, there are snakes on it, and you have a broken leg. This whole thing situation is pretty jackshaw.
Person 2: Fuck you.

Person 1: I just won a Pulitzer Prize for the novel I wrote about the adventure we survived 10 years ago! Fighting tigers, kissing natives, swinging on vines to escape hungry Howler monkeys, breaking bones and crossing decrepit bridges, I couldn't even make up that adventure if I tried.
Person 2: Cheers. *takes shot of bourbon*

Example 2

Wow, that Urban Dictionary definition is pretty jackshaw, but I kinda like it.
by tyq July 16, 2014

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