Jail buddies are two friends who stick together no matter what and have fun. It doesn't necessary imply them being best friends but rather emphasize on their supportive nature. The word "Jail Buddy" is meant to signify that a person will always bail his/ her friend out of difficult situations and will always stand by the other.
Simon, thanks for saving me from the principal. You are my true Jail Buddy.
by dudechicjailbudy May 11, 2010