10 Most Funny Poems about Prisoners

Dive into a world of humor with our collection of the 10 Most Funny Poems about Prisoners. These whimsical verses offer a lighthearted take on life behind bars, proving that even in the most unexpected places, laughter can be found. Join us as we explore the comedic side of confinement!

Funny Poems about Prisoners

1. The Escape Artist’s Mishap

This poem humorously paints a scene of a prison escape artist who, while being incredibly skilled, always ends up back where he started.

In a cell so bleak and small,

Harry planned his great escape fall,

Over walls and past the gate,

Yet his dinner date just couldn’t wait.


He’d dig and crawl, evade the light,

Into the tunnel, out of sight,

But the scent of pie, so fresh and near,

Led him back, year after year.


For every time he’d find the route,

His stomach’s call he could not mute,

Though free at last, he’d soon return,

For a slice of pie, his only concern.

2. The Singing Inmate

This poem describes an inmate whose only crime is his terrible singing voice, leading to humorous reactions from his fellow prisoners.

In Cell Block Three, there’s quite a show,

Where Jeff belts out tunes, high and low,

His voice, it seems, a bit off-key,

A “crime” that all can clearly see.


Other inmates beg and plead,

“Silence your voice, or we’ll concede!”,

But Jeff, undeterred, continues on,

His “concerts” from dusk till dawn.


“Music’s my soul!” he’d always say,

While others wished he’d just sway away,

For in prison, the greatest misery,

Is Jeff’s never-ending singing spree.

3. The Fashionista Felon

A light-hearted tale of a prisoner who is more concerned about his outfit than his time in prison.

Locked away but not distressed,

Carl cared only for how he’s dressed,

Stripes, he thought, are quite chic,

A fashion statement, unique and sleek.


Matching shoes, a belt so tight,

He’d parade around, day and night,

“Who cares about freedom,” he’d proclaim,

“When my outfit’s on point, and not so lame!”


Others might’ve seen prison as a bane,

But Carl, with his style, felt no pain,

For him, the biggest prison sin,

Was a fashion faux pas from within.

4. The Failed Breakout

A humorous account of a prisoner who makes numerous attempts to break out, but somehow always misses the mark.

Tommy tried once, he tried twice,

To escape the prison, wouldn’t that be nice?

But every time, a new blunder,

Made the guards laugh and wonder.


First, he used a spoon, so dull and slow,

Then a rope that was way too low,

Next, a ladder, but oh what a jest,

It was too short, unlike the rest.


His plans, though grand, always askew,

Made him famous, as his legend grew,

The prisoner who always tried to flee,

But failed so comically for all to see.

5. The Gourmet Gangster

This poem describes a mobster who, while fearsome on the streets, is best known in prison for his culinary skills.

Tony, the mobster, fierce and bold,

In the outside world, stories told,

But inside bars, a different tale,

Of soufflés, pies, and fresh kale.


He’d trade a secret sauce for a favor,

His lasagna, oh, a flavor to savor,

Enemies outside, but inside, a chef,

His recipes guarded, kept to himself.


Who’d have thought, this man of might,

Would be cooking up a storm every night?

From feared gangster to prison’s gourmet star,

Tony’s kitchen tales, by far the most bizarre.

6. The Sleepy Bandit

A funny depiction of a prisoner who is constantly sleepy and can’t stay awake, much to the amusement of others.

Rob, the bandit, swift and sly,

In prison, he’d always sigh,

Not from remorse or feeling low,

But from sleep, he couldn’t forego.


Mid-sentence, he’d start to snore,

Dreaming of heists and so much more,

Guards and inmates would chuckle and grin,

As Rob’s naptime would yet again begin.


Some say it’s a ruse, a clever ploy,

But all agree, it brings them joy,

To see the sleepy bandit, without a plan,

Dreaming away, in the prison van.

7. The Artist Behind Bars

The story of a prisoner who becomes an accidental artist, using the walls of his cell as a canvas.

Mike wasn’t an artist, not at all,

But in his cell, he’d draw on the wall,

Doodles and sketches, without a care,

A gallery of thoughts, laid bare.


The guards soon noticed, this hidden trait,

A talent discovered, albeit late,

They’d tour his cell, a museum of sorts,

Admiring his sketches of ports and forts.


From notorious to notable, Mike did evolve,

With every sketch and artistic solve,

Though confined, his spirit free,

An artist behind bars, for all to see.

8. The Tattletale Thief

This poem describes a prisoner who, despite his tough exterior, can’t help but spill the beans on every minor mischief.

Jake, the thief, quick and shifty,

In prison, became so very thrifty,

Not with money, goods, or stash,

But with tales and stories, in a flash.


He’d tell on this, he’d tell on that,

From a smuggled snack to a new rat,

No secret safe, when Jake’s around,

For his tattletales did abound.


The prisoners groaned, the guards did cheer,

For Jake, the snitch, was always near,

A tattletale thief, a paradox indeed,

His tales, the prison’s daily feed.

9. The Fitness Freak Felon

A light-hearted tale of a prisoner who is obsessed with staying fit, making the prison gym his personal haven.

Larry loved to lift, to jog, to sprint,

In prison, he’d never relent or hint,

Of tiredness, fatigue, or any strain,

For fitness was his only aim and gain.


Push-ups at dawn, squats at dusk,

A fitness regimen, intense and brusk,

Inmates would watch, in awe and glee,

As Larry flexed for all to see.


He may be locked, confined, and tight,

But his fitness goals took full flight,

In a world of bars, chains, and cell,

Larry’s gym stories were what inmates would tell.

10. The Clueless Conman

This poem humorously narrates the tale of a conman who, despite his confidence, is always clueless about his surroundings.

Eddie, the con, so sly and neat,

Yet in prison, always offbeat,

He’d mistake a guard for an old pal,

And the warden’s office, for a cocktail hall.


He’d ask for champagne, caviar on toast,

In the cafeteria, to everyone’s roast,

Confident yet clueless, he’d always be,

A source of endless laughs and glee.


He’d plot an escape, but the wrong way round,

Head for the roof, when he’s underground,

With every move, inmates would jest,

“Here comes Eddie, doing his best!”


Though a con outside, within those walls,

His clueless acts were like humorous brawls,

For even in prison, where moods can be grim,

Eddie’s antics kept spirits from growing dim.

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