Cartoons: Jail Fails

Prison is no laughing matter, but these felons are funny!

Two prisoners talking in a cell

Weekly Newsletter

The best of The Saturday Evening Post in your inbox!

SUPPORT THE POST

Want even more laughs? Subscribe to the magazine for cartoons, art, inspiring stories, fiction, humor, and features from our archives.

 

Two prisoners talking in a cell
“Ten or twenty years from now we’ll look back at all this and laugh.”
Peter Wyma
April 28, 1956

 

Escapee in a dog costume is caught and is confronted by the prison guards and the wardenj
“Well, you didn’t make it, Slick, but it certainly was an interesting jail break.”
Gallagher
February 13, 1954

 

Prisoner is caught trying to saw through the bars and tries to explain it away.
“Frankly, I’m quite worried. I think someone’s been trying to break in.”
Huffine
January 20, 1945

 

Two prisoners talking in a cell
“Naturally, I figured, with inflation and everything, the dividing line between petty and grand larceny would have been raised considerably.
Chon Day
January 19, 1952

 

A guard speaks to his former bank's coworker
“Glad everything is find at the office. I bet old K.C. is now personally taking the money to the bank.”
J. Kieman
January 14, 1956

 

Former political candidate and now jailed crook speaks to a journalist during visitation
“You may say that I am definitely not a candidate for public office at this time.”
S. Hunt
October 22, 1955

 

Two prisoners talking in a cell
“REALLY? Why, he was my attorney too!”
Irwin Caplan
September 20, 1952

 

Prison guards find a machine gun underneath an inmates cot, who is trying to act like he never knew it was there.
“Well, no darned wonder I slept so uncomfy last night.”
Al Johns
September 3, 1955

 

Two prison inmates discuss a possible escape plan.
“I’ve been trying to think of something that will brighten up the place. What about a tunnel?”
Chon Day
June 18, 1955

 

Want even more laughs? Subscribe to the magazine for cartoons, art, inspiring stories, fiction, humor, and features from our archives.

Become a Saturday Evening Post member and enjoy unlimited access. Subscribe now

Recommended

Comments

  1. A really great batch selected this week! #1 at the top is my favorite here. The facial expressions are priceless! Next has to be #4 regarding inflation. Technically he makes a good point—sort of. #6. I guess he isn’t a candidate for public office because he got caught doing whatever he’s doing time for. #8 &9 about the firearms (!!) and the tunnel are really funny too. Give the Post gets a ‘get out of jail card for free’ card. Case dismissed! 🙂

Your email address will not be published. Required fields are marked *