Jailbox Smart 

When you spend 15 minutes explaining to a waitress what a motorcade is, and she has a blank look on her face and asks you if that's one of those jailbox things.

Wow, that waitress is jailbox smart!

Jailbox Smart by Mr. Sonoma July 28, 2007

Jailbox Smart 

When you spend 15 minutes explaining to a waitress what a motorcade is, and she has a blank look on her face and asks you if that's one of those jailbox things.

Wow, that waitress is jailbox smart!

Jailbox Smart by Mr. Sonoma July 27, 2007

jailbot 

is a tombstone-shaped levitating robot that performs tasks in and around Superjail, such as piloting vehicles and transporting prisoners. He essentially acts as the Warden's gofer. Jailbot is mute, with a dot-matrix screen that displays a simple expressive face. He is gratuitously vicious in most things, often killing numerous people in attempting to accomplish his task. Christy Karacas described him as a "red headed stepchild... seeking approval."

Jailbot, you are the only one I can trust these days.

jailbot by Pridurak1357 February 9, 2010

jailboss 

An evil girlboss.

“OMG! Look at her! She just dropped her toxic best friend in front of everyone! What a jailboss!”

jailboss by Sopherpherwerpher June 3, 2021

Jailboi 

A person with the most trust in everybody and a good person. A master at Nintendo games and beat his friends.

Jailboi ur a jew

Jailboi by Jailboi July 29, 2022