Prison Guard Henry (Henry Rollins) in Lost Highway (1997)

Gaoler (Simon Pegg) in The Reckoning (2004)

Prison Guard Jamberg Saivon (Michael Ian Black) in The Ten (2007)

Hateful Guard at Maryland Training School for Boys (Willem Dafoe) in Cry-Baby (1990)
GUARD: “We’re going to give you a haircut tomorrow, pretty boy. You ever hear of a Whiffle?”
[CRY-BABY gags]
Hateful Guard at Maryland Training School for Boys (Willem Dafoe) in Cry-Baby (1990)
GUARD: “We’re going to give you a haircut tomorrow, pretty boy. You ever hear of a Whiffle?”
[CRY-BABY gags]

Hateful Guard at Maryland Training School for Boys (Willem Dafoe) in Cry-Baby (1990)

GUARD: “We’re going to give you a haircut tomorrow, pretty boy. You ever hear of a Whiffle?”

[CRY-BABY gags]

Alcatraz Tour Guide John ‘Vicky’ Johnson (Phil Hartman) in So I Married An Axe Murderer (1993)

“Now this is something the other tour guides won’t tell you. In this particular cell-block, Machine Gun Kelly had what we call in the prison system, a “bitch”. And one night in a jealous rage Kelly took a make-shift knife or “shiv”, and cut out the bitch’s eyes. And as if this wasn’t enough retribution for Kelly, the next day he and four other inmates took turns pissing into the bitch’s ocular cavities.”

[short pause]

“This way to the cafeteria!”