Best definition
Being up to something anytime anywhere that is totally bad ass and is funny as hell is utterbadassery. It can be compared to, but is more than, dropping huge water balloons off of tall buildings onto people, exposing yourself to a cop, stealing an old man’s walker, fucking with a mime or one of those silver cowboys or one of the buckingham palace guards, telling airport security that your friend is a terrorist, telling airport security that YOU are a terrorist, grabbing a random woman’s ass, stealing stuff in a nun or priest outfit, sleeping with as many of your friends’ girls as you can at once, and shit like that. It’s more like doing all of these things at once, and not giving a damn about what happens.
Despite all the Fall Out Boy references, the term was coined (as far as I can tell) by OK Go
Obama: Utterbadassery. This is why I was elected. Utterbadassery. I just love saying it.

Urban Dictionary is a prime example of utterbadassery.

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