Clif Kosterman, who plays "Tiny", is the real life longtime bodyguard of Jensen and Jared. The three men are very close friends.
While in the prison, Dean says to Sam, "You from Texas all of a sudden?" The actors that play Sam and Dean were both raised in Texas.
Jensen Ackles celebrated his birthday (March 1) on location at the prison set during filming for this episode. At the beginning of the day, the 50 extras dressed as prisoners sang "Happy Birthday" to him in the yard.
When Dean stands up, hands full of cigarettes and shouts out, "Hey fellas, who's ready to deal?" You can see Jared Padalecki grinning and mouthing the line along with Jensen Ackles.
When Dean is in solitary, he tells Lucas, "I said I wish I had a baseball - like Steve McQueen." This is a reference to the scene where Steve McQueen's character repeatedly bounces a baseball on the walls of his solitary confinement cell from the film classic The Great Escape (1963).