Jailhouse Humorist T-Shirts

Make a bold statement with our jailhouse humor T-shirts—fun, irreverent designs that suit anyone with a mischievous sense of humor and a fondness for offbeat comedy.

All Products Prints T-Shirts Mugs Pillows

Prisoner Crossing

from $19.00

"They weren't very friendly when they proscuted me for obtaining loans under false names."

"They weren't very friendly when they proscuted me for obtaining loans under false names." mockup

"They weren't very friendly when they proscuted me for obtaining loans under false names."

from $19.00

'My daughter tells me you're allowed to come home on weekends...is that from college?'

'My daughter tells me you're allowed to come home on weekends...is that from college?' mockup

'My daughter tells me you're allowed to come home on weekends...is that from college?'

from $19.00

'White collar crime for me . . . what are you in for?'

'White collar crime for me . . . what are you in for?' mockup

'White collar crime for me . . . what are you in for?'

from $19.00

"I've got him! I've got him!...Now what?"

"I've got him! I've got him!...Now what?" mockup

"I've got him! I've got him!...Now what?"

from $19.00

"See you later. Do you want the door closed?'

"See you later. Do you want the door closed?' mockup

"See you later. Do you want the door closed?'

from $19.00

"Hit the escape key."

from $19.00

"How could this happen? I was a meticulous bookkeeper -- with both sets."

"How could this happen? I was a meticulous bookkeeper -- with both sets." mockup

"How could this happen? I was a meticulous bookkeeper -- with both sets."

from $19.00

'What a doofus! - He started an upside-down pyramid scheme!'

'What a doofus! - He started an upside-down pyramid scheme!' mockup

'What a doofus! - He started an upside-down pyramid scheme!'

from $19.00

'This one's called '25 to Life'.' mockup

'This one's called '25 to Life'.'

from $19.00

"Apparently it's OK to clone sheep but not hundred-dollar bills"

"Apparently it's OK to clone sheep but not hundred-dollar bills" mockup

"Apparently it's OK to clone sheep but not hundred-dollar bills"

from $19.00

"First the shirt, then the shovel, now the saw. I think the guards like me"

"First the shirt, then the shovel, now the saw. I think the guards like me" mockup

"First the shirt, then the shovel, now the saw. I think the guards like me"

from $19.00

We have a saying around here. Indict me once, it's my lawyers fault. Indict me twice, it's my fault.

We have a saying around here. Indict me once, it's my lawyers fault. Indict me twice, it's my fault. mockup

We have a saying around here. Indict me once, it's my lawyers fault. Indict me twice, it's my fault.

from $19.00

'I let my inner child out to play, and he held up a convenience store.'

'I let my inner child out to play, and he held up a convenience store.' mockup

'I let my inner child out to play, and he held up a convenience store.'

from $19.00

'I thought I'd beaten the rap, and then they pulled Murphy's law on me!'

'I thought I'd beaten the rap, and then they pulled Murphy's law on me!' mockup

'I thought I'd beaten the rap, and then they pulled Murphy's law on me!'

from $19.00

"I'm finding it difficult to keep alive the little embezzler within."

"I'm finding it difficult to keep alive the little embezzler within." mockup

"I'm finding it difficult to keep alive the little embezzler within."

from $19.00

'Never take the stand in your own defense. The judge can reach you with the gavel.'

'Never take the stand in your own defense. The judge can reach you with the gavel.' mockup

'Never take the stand in your own defense. The judge can reach you with the gavel.'

from $19.00

At least you have security!

from $19.00

'They've bugged our conversation.' mockup

'They've bugged our conversation.'

from $19.00

Cartoonist draws bomb next to prisoner. mockup

Cartoonist draws bomb next to prisoner.

from $19.00

'Well, you're not acting like you have every confidence in me.'

'Well, you're not acting like you have every confidence in me.' mockup

'Well, you're not acting like you have every confidence in me.'

from $19.00

"They say you're good with forgeries?" mockup

"They say you're good with forgeries?"

from $19.00

"No, I've only been in two years - that's how many cell mates I've had."

"No, I've only been in two years - that's how many cell mates I've had." mockup

"No, I've only been in two years - that's how many cell mates I've had."

from $19.00

"They say you're a cybercriminal." mockup

"They say you're a cybercriminal."

from $19.00

"We get this place renamed the 'men-only prison,' and women will be demanding admission."

"We get this place renamed the 'men-only prison,' and women will be demanding admission." mockup

"We get this place renamed the 'men-only prison,' and women will be demanding admission."

from $19.00

"Oh, give me a break. My attorney's book has sold twice that many copies."

"Oh, give me a break. My attorney's book has sold twice that many copies." mockup

"Oh, give me a break. My attorney's book has sold twice that many copies."

from $19.00

Prison Reading Material

from $19.00

When staffing agencies screw up.

from $19.00

"I had money problems- forged fivers the wrong colour!"

"I had money problems- forged fivers the wrong colour!" mockup

"I had money problems- forged fivers the wrong colour!"

from $19.00

'OVERCROWDED-I'll say it's OVERCROWDED!'

'OVERCROWDED-I'll say it's OVERCROWDED!' mockup

'OVERCROWDED-I'll say it's OVERCROWDED!'

from $19.00

'I mistakenly thought that 'mutual' meant the funds were equally mine to use.'

'I mistakenly thought that 'mutual' meant the funds were equally mine to use.' mockup

'I mistakenly thought that 'mutual' meant the funds were equally mine to use.'

from $19.00

'Smooth move -- Now we're in REAL trouble!'

'Smooth move -- Now we're in REAL trouble!' mockup

'Smooth move -- Now we're in REAL trouble!'

from $19.00

'I was on 'AMERICA'S MOST WANTED', captured on 'COPS', tried on 'COURT TV' and sentenced to 10 years of basic cable.'

'I was on 'AMERICA'S MOST WANTED', captured on 'COPS', tried on 'COURT TV' and sentenced to 10 years of basic cable.' mockup

'I was on 'AMERICA'S MOST WANTED', captured on 'COPS', tried on 'COURT TV' and sentenced to 10 years of basic cable.'

from $19.00

Convict Decor

from $19.00

Man in arrow suit - 'I'm in for white collar crime.'

Man in arrow suit - 'I'm in for white collar crime.' mockup

Man in arrow suit - 'I'm in for white collar crime.'

from $19.00

Jailhouse Humorist T-Shirts Collection

Jailhouse Humorist Mugs

Explore our full range of jailhouse humor mugs—funny designs for those who enjoy a rebellious twist to their coffee moments.

Jailhouse Humorist Pillows

Check out our jailhouse humor pillows—funny and cheeky decor pieces that bring a humorous touch to any room.

Jailhouse Humorist Prints

Browse our jailhouse humor prints—bold, humorous artwork that adds a rebellious punchline to your wall art collection.