5 Jokes For Prison Guard

Double Meaning Jokes

Updated on: Jun 20 2025

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The Aspiring Stand-up Comedian Turned Prison Guard

Juggling the dream of making people laugh with the reality of enforcing rules
Why did the stand-up comedian prison guard get in trouble? He accidentally handed an inmate a "get out of jail free" card during a game of Monopoly.

The Tech-Savvy Prison Guard

Dealing with outdated security systems and the challenges of keeping up with technology
The tech-savvy guard once tried to introduce virtual reality to the prison. Inmates loved it until they realized the virtual bars were just as confining as the real ones.

The Zen Prison Guard

Finding inner peace while dealing with chaotic inmates
The Zen prison guard tried to introduce yoga to the inmates. Let's just say the downward dog position took on a whole new meaning in a cell.

The Overly Paranoid Prison Guard

Constantly fearing escape attempts and inmate schemes
The paranoid guard once confiscated a bag of marshmallows from an inmate. Why? He was convinced they were secretly planning to build a fluffy escape route.

The Overly Enthusiastic Prison Guard

Balancing friendliness with maintaining authority
Ever heard about the prison guard who tried to organize a comedy night for the inmates? It went well until someone yelled, "I object!" during his routine.

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