jail fail 

Any time you undertake an action where the probable outcome is a quick trip to jail. Jail fails are the second from the bottom in the heirarchy of fails.

See also: Epic fail, death fail

Steve: So I'm pretty sure I saw you pedipass last night.
Austin: Yeah, I hope it doesn't turn into jail fail.

jail fail by SargeSmith April 25, 2008

jail buff 

the kind of buff you only get from being in jail for multiple years having nothing to do but work out.

Like Val Kilmer's bod at the end of the movie Felon or Edward Norton at the end of American History X.

For example:

" I met this totally hot guy at the beach the other day, he was fucking jail buff! "

jail buff by sweetcheeksO7 October 9, 2008

jail punk 

the bitch in a prison. they are usually in jail for tax evasion or molesting their children. these are the guys who cry on their first night and try to avoid the scary black men who stare at them and have the bottom of their shirts tied in a knot. jail punks get pounded in the anus quite often in the shower and in their cell. they usually get protection from the black guy they share their cell with, even though that is the same guy plowing them every night.

burly black guy wearing lipstick: hey, boy! get ova he'a. we is gonna play ourselves some pony express!

jail punk: yessir. please be gentle.

burly black guy wearing lipstick: NOT TODAY, BOY! DROP THEM PANTIES!

jail punk: YESSIR!

jail punk by clevelandsteamer September 5, 2005

Jail Bird Syndrome 

A condition in which one has feelings of attraction towards many random women, even those less attractive, due to a period of isolation from society.

Man, after finishing my final exam, I felt some major jail bird syndrome on my way to work.

Guy: dude that girl is so hot. Guy2: what?! No she isn't, you must have jail bird syndrome... get out more.

Jail Bird Syndrome by T-boneCgy August 19, 2011

Jail Broken 

A term used for a iphone that has been illegally manipulated to use a network that it isn't on.

My iphone is from AT&T, but it has been jail broken, so it can connect to Verizon's network.

Jail Broken by oqukm March 31, 2010

jail bait 

Underage females that usually attract older men twice their age. They say they shave, but in reality, they have yet to hit puberty.

Big Steve loves him some jailbait. His one girlfriend graduated... from the 8th grade!

jail bait by Ghst September 12, 2004

jail tail 

A small ponytail favored by prisoners, ex-cons, and meth dealers.

That guy's jail tail and prison tats are freaking me the hell out.

jail tail by buddybacon March 21, 2008