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habitrail for humanity 

Enclosed skywalks between office buildings, as seen in downtown areas. Based upon the visual similarity with hamster habitrail tubes. Often shortened to simply "habitrail."
It's raining; let's take the habitrail to the restaurant
habitrail for humanity by Rod March 2, 2005

habitual line stepper 

One who constantly steps over "the line" whatever that line may be. This has the effect of forcing you as an observer to set him or her straight with physical force or the threat of physical force.

(from Chappelle's Show: Charlie Murphy True Hollywood Story)
RICK JAMES "Charlie Murphy!!! (punch to the head, leaving a mark)

Then Charlie Murphy proceeds to kick Rick James' ass because he's gotta check that shit so it don't happen again, forcing him to stop being a habitual line stepper.

habitualize 

I am trying to habitualize going to the gym every morning.
habitualize by Glightnin7 April 8, 2010

habitual line stepper 

One who always goes over the line. One who always goes too far and exercises no apparant regard for the consequences. Term was coined by Charlie Murphy on Chapelle's Show when describing the antics of Rick James.
Rick James was an habitual line stepper.

Greg owes me utilities and just had sex with my girlfriend for the third time this week. That guy is such an habitual line stepper.

Habitual dumb ass 

An involuntary idiotic behavior pattern regularly followed. Regular disposition or tendency to act in a stupid manner or think or say thoroughly stupid things.
"hey man do you keep getting those urban dictionary word of the day emails from Sami?"

"yeah bro amongst a million stupid text messages about nothing, but it doesn't bother me because I know that Sami will always be a habitual dumb ass!"
Habitual dumb ass by AbdelHater August 10, 2012

Habitually Offended 

An individual so desperate for attention that they actively seek out anything they may possibly take offense and claim outrage to, caring nothing for the potential consequences of their actions so long as they gain the attention they feel they deserve for their invented slights and hardship.
Will is so habitually offended that he started trolling internet TV shows just to get his fix.
Habitually Offended by T1R3D January 30, 2019