Contest No. 120 starts right now.
Briefly, here are the details: I’ll supply a drawing of one of my old
Your caption (or captions) will be posted after I review your submission. Also, no captions at all will be posted for the first few days of each contest. This is to give everybody a chance to submit their spontaneous, gut-instinct caption without fear of discovering that it was ripped off by somebody else’s similar spontaneous caption. This is an equal opportunity contest!
There is no limit on the number of captions you can enter for each drawing. Entries will be accepted and posted for one week, after which a winner will be announced and the winning caption will be printed. Below that I will also print my original caption.
The cut-off time and date for you to send in your captions is midnight Tuesday, July 4, 2017.
I will be the sole judge. The winning caption will be the one I judge to be the funniest one submitted (not necessarily the one that matches or comes closest to my original caption). Additional rules and regulations, for those of you who need such things, can be found here.
Below is the drawing that needs your funny captions.
109 Comments
Hi, welcome to the jailhouse
Hi, welcome to the jailhouse hotel. Relaxing and friends are
our goal. Enjoy your stay.
“I have to tell you, I feel
“I have to tell you, I feel so much more relaxed now that I can’t read peoples’ comments on the Internet.”
My crime was landing on Go to
My crime was landing on Go to Jail while Monopoly
At least we’ll get a break
At least we’ll get a break from hearing about the never-ending Trump tweets.
No thanks, I prefer to keep
No thanks, I prefer to keep my legs crossed.
Well, I guess I won’t be
Well, I guess I won’t be needing to apply for conjugal visits.
All in all I had a pretty
All in all I had a pretty good run in the market, right up to the time my father-in-law wanted his money back.
This is great! I finally have
This is great! I finally have free healthcare!
“Well, it’s been ten years
“Well, it’s been ten years now…what do you say we rearrange the furniture?”
“Your kidding!…and all
“Your kidding!…and all these years I thought you were just my imaginary friend.”
I haven’t committed any crime
I haven’t committed any crime. I’m just here to get away from my wife.
“I was thinking about re
“I was thinking about re-arranging the furniture today”!
“You want to go out for
“You want to go out for dinner tonight or just order a pizza”?
“Yeah, I used to think life
“Yeah, I used to think life is to short too till I got here, but five to fifteen seems like forever!”
“So how’s the nightlife
“So how’s the nightlife around here”?
“So what’s your favorite
“So what’s your favorite prison movie”?
“So I says”, “Your Honor, who
“So I says”, “Your Honor, who died and made you Judge”?
“That’s funny, “life is too
“That’s funny, “life is too short”! “The judge told me the same thing when he sentenced me”!
“MAN, I could kill again for
“MAN, I could kill again for a double cheeseburger and fries”!
“What are you getting the
“What are you getting the Warden for Christmas”?
“When I get out, I want a
“When I get out, I want a little place by myself, nothing fancy, with no neighbors around, they take so long to bury”!
“What time did you make our
“What time did you make our tee-off reservations for”?
“Since I’ve been here I
“Since I’ve been here I hardly ever sleepwalk anymore”!
“You wanna play Monopoly, I
“You wanna play Monopoly, I’ll spot you the ‘Get Out of Jail Free’ card”!
“I waiting to hear from the
“I’m waiting to hear from the Governor about my parole, luckily he’s in the cell next to us”!
“Yeah, I read ‘A Brief
“Yeah, I read ‘A Brief History of Time’, by some ex-con, Steven Hawking, he must a got an early parole”!
I knew mom was serious about
I knew mom was serious about our curfew.
Oh boy, bagels for breakfast.
Oh boy, bagels for breakfast.
“Have you seen The Shawshank
“Have you seen The Shawshank Redemption?”
The beds make up for the
The beds make up for the staff’s attitude.
Tell me, is it possible to
Tell me, is it possible to receive travel brochures while being incarcerated?
I asked for conjugal visits,
I asked for conjugal visits, and they sent you.
My mother-in-law said that I
My mother-in-law said that I would do anything to avoid her. Now, she has been proven right.
I was told my cell might be
I was told my cell might be “bugged.” But, the only bugs I have found have legs.
Jack, I want you to paint me
Jack, I want you to paint me like one of your frenchg girls…
My advisor in college
My advisor in college indicated that I should study the criminal justice system. Now, I can appreciate everything I’ve done wrong in life.
All I can think about when
All I can think about when sleeping is “free” time, “free” time, “free” time….etc. Then I wake up and see you.
I am serving time for bigamy.
I am serving time for bigamy. But, most of my mail is from lonely women who want to marry me.
My shyster lawyer said the
My shyster lawyer said the bad news about being in jail is like being on a crowded cruise ship. The good news is you never get sea sick.
The final punishment that I
The final punishment that I received in jail was from my wife. She cancelled my viagra prescription.
My company said I had a
My company said I had a “golden parachute” clause in my contract. When things went bad, they tossed me out of a plane with my parachute on, and I landed on top of this penitentiary building.
I am a federal “employee” in
I am a federal “employee” in training. I count the years, hours, and minutes until I serve my time.
It has been said, “If you
It has been said, “If you free your mind, your body will follow.” In my case though, I keep bumping into walls.
Before I was incarcerated, I
Before I was incarcerated, I invested all my stolen money in Bernie Madoff’s high interest rate projects. By now, I should be a billionaire on paper.
I believe in the 2nd
I believe in the 2nd amendment, except when guns are pointed at me.
There are some things money
There are some things money can’t buy, like the services of a jail house interior designer.
You know the old saying, “If
You know the old saying, “If you can’t beat em, then join em.” I am now a bona fide member of the “Big Bubba” club who lives several cells down the corridor.
I spotted my old cook
I spotted my old cook sergeant from my army days. He was serving bean soup and spicy sausage stew for the main course. Needless to say, I’m on an extended hunger strike.
I told the warden that I was
I told the warden that I was a sailor in the navy. He said, “That was good,” and assigned me to the “mop and pail” detail.
Have you heard of the “bird
Have you heard of the “bird man of alcatraz?” Well, the judge in my court proceedings called me the future “birdbrain of little alcatraz.”
The other inmates loved my
The other inmates loved my tattoos. They showed me their homemade knives, and said they would graciously add more tattoos to my body collection.
Just like me, everyone in
Just like me, everyone in this prison is innocent. The only difference is my mother-in-law hired my attorney, and he was compelled to plead me guilty in court.
My ex-boss sent me an ISIS
My ex-boss sent me an ISIS flag for the Fourth of July. He instructed me to wave it to the prison crowd for Independence Day and scream, “Allahu Akbar!”
“Let’s be adventurous and do
“Let’s be adventurous and do something different today…you sit and I lie.”
“We’ve both said everything
“We’ve both said everything at least a thousand times, so how about if we just shut up for the next five years!”
“OK, now I’ll play the client
“OK, now I’ll play the client and you be the therapist.”
“Funny how times flies when
“Funny how times flies when you’re having a good time.”
“I’m breaking out tonight..
“I’m breaking out tonight…you got any Clearasil?”
“Well that’s refreshing…You
“Well that’s refreshing…You’re the first guy I met in here who’s guilty!”
1. “Well at least they gave
1. “Well at least they gave us a room with a view.”
2. “Did you have anything to do with that mint I found on my pillow last night?”
3.”What I wouldn’t give for some curtains on our window!”
4. “Just to show you how much I like you, you can have the peas on my last meal tomorrow.”
5. “There’s always something to be grateful for…like the fact that neither one of us plays the accordion.”
“Well, you don’t look like a
“Well, you don’t look like a serial killer…but then, I don’t look like a chiropodist.”
I have only two insignificant
I have only two insignificant medical problems. One is sleep walking, and the other is chronic flatulence.
My wife couldn’t post the
My wife couldn’t post the $2000 bail money, because she said she needed a spa treatment and a make-over retreat.
By watching the inmates in
By watching the inmates in this prison, I can appreciate the phrase, “The dog days of summer.”
When I am released from
When I am released from prison, Maury Povich invited me on his show to discuss, “Whose the father of the babies?”
My victim wrote me to “wake
My victim wrote me to “wake-up and smell the roses.” But, there are no flower gardens on these premises.
When I consider what we eat
When I consider what we eat in prison to what those poor people of Ethiopia eat, then I realize what lucky people they are.
I voted for President Trump
I voted for President Trump to “MAKE AMERICA GREAT AGAIN.” He notified me that when I am released from jail, that I will receive from him a special visa to visit North Korea.
My friends say that I am the
My friends say that I am the “butt” of all their prison jokes. Personally, I never knew I had such a big butt.
I asked the jail guard for
I asked the jail guard for some nude magazines. He placed a subscription order for me to the World Wildlife Association.
Part of me wants to be on the
Part of me wants to be on the outside, and a part of me wants to stay where I am. Well, it looks as though the part of me who wants to be on the inside has won.
No one knows the pain I’ve
No one knows the pain I’ve seen in my lifetime. It happened to be the flashing lights of a police cruiser.
My estranged wife used to
My estranged wife used to call me a lousy son of a bitch. I never knew why she used the word “lousy.”
Since we live and work
Since we live and work together here in prison, can I use you for a job reference once I leave here?
Judge Judy once said, “Don’t
Judge Judy once said, “Don’t piss on my leg and call it rain.” I would never call it rain. After all, It favors more like lemon juice, and that’s the correct term.
Do you have any hobbies
Do you have any hobbies beside robbing banks? So, you like to watch gangster movies as a hobby. What a surprise!
Lawyers are known as “sharks,
Lawyers are known as “sharks,” because of their sometime shady practices with sharp biting results. Well, my lawyer was immature with no shark teeth, so all he could do was smile while I suffered with him.
Hey, don’t have to work, pay
Hey, don’t have to work, pay bills, free food, free medical, free everything…I’M STAYING!!!!’
“Well,Marvin,we`ve got plenty
“Well,Marvin,we`ve got plenty of time now to write lots of captions to those Eli Stein Cartoons.” “We sure have,Cary.”
After discussing my vaccine
After discussing my vaccine record with the prison doctor, he decided that I needed a set of rabies vaccines. After all, foaming at the mouth is scary, since you do not drink beer in prison.
Do you know that world
Do you know that world hostilities are escalating. Also, the stock market crashed, and the value of the dollar is the worst in decades. The economy has forced a freeze on job hiring with no salary increases. You don’t want to learn the “bad” news!
1st inmate: One thing I miss
1st inmate: One thing I miss is a big fat raw steak.
2nd inmate: Oh, do love to eat steaks often?
1st inmate: No, the steak is for my black eye that another
inmate gave me on the parade grounds.
I missed my son’s birthday
I missed my son’s birthday this month. He said not to worry, since he borrowed my hidden gun at home to persuade a toy store to give him some gifts in my name.
I want to practice
I want to practice ventriloquism with my spare time. Since your mouth moves and you don’t have much to say, would you volunteer to be my dummy?
Last week the toilet backed
Last week the toilet backed-up. The jail attendant told me to rotate my hand in the toilet until it is unstopped. I hollowed back, “I’m keeping it in for now!” But, I wasn’t referring to my hand.
I talked to my jail house
I talked to my jail house dietician to make sure I am getting the “biggest bang for the buck.” I said I needed to avoid greasy food, spicy food, foreign food, and tasteless food. He asked me if I was sure that I wanted gun powder with my venison.
My nickname is “Scratch.” My
My nickname is “Scratch.” My unfortunate experience in Malaysia caused me to contract this horrible incurable disease. By the way, you have that same reddish-brown spot on your arm.
Do you believe in space
Do you believe in space aliens? You don’t? We need to make contact with them, so that we can get beamed out of here.
In this facility everybody is
In this facility everybody is treated the same without discrimination. Therefore, everybody is equally miserable!
All holidays are celebrated
All holidays are celebrated with spiritual prayers. As if, the other mundane days don’t matter.
1st inmate: Billy Bob, do you
1st inmate: Billy Bob, do you rinse your mouth at night?
2nd inmate: Noooooah, but I used to chew tobacco and spit.
Mistakenly, I heard morse
Mistakenly, I heard morse code last night. Come to find out, even the damn rats were trying to break-out of this prison!
So, I reported to the jail
So, I reported to the jail guard that they had a rat problem in this facility. He responded that, “Every convict in this building will ‘rat’ for the right price.”
1st inmate: What did you
1st inmate: What did you major in college?
2nd inmate: Finances and accounting.
1st inmate: You must be a smart guy.
2nd inmate: Not really, I was busted for bank fraud.
They have a “Lost and Found”
They have a “Lost and Found” department in this building. But, the only things lost and found are generally false teeth and used condoms.
It is better to “have loved
It is better to “have loved and lost, then to never have loved at all.” Well, it worked for my high maintenance attorney handling my divorce case.
Well, today should be a
Well, today should be a better day than yesterday. That’s because, my blood wounds have clotted today.
1st inmate: What animal would
1st inmate: What animal would you choose, if you could be
reincarnated?
2nd inmate: A blood sucking “parasite” like my attorney.
1st inmate: Is he really a vampire?
1st inmate: Once I was asked
1st inmate: Once I was asked by a politician for my support.
I replied, “What laws did you break?”
2nd inmate: Did you recommend a good “country club” prison?
“CONSTIPATION!” What all
“CONSTIPATION!” What all inmates dream to achieve.
Glad to see you are relaxed,
Glad to see you are relaxed, my hostess skills are working
“An eye for an eye, a tooth
“An eye for an eye, a tooth for a tooth.” No wonder this prison looks like a pirate ship!
The authorities threatened me
The authorities threatened me with the death penalty. But, in my opinion I die a little every day just being here. After a short time in this insane and crazy place, I’m mostly dead anyway.
Every night the rats walk off
Every night the rats walk off with something, as my toothbrush, or my pencil, or my pictures, etc. The rats have more jail house supplies than I do.
Scarface (nickname), “You’re
Scarface (nickname), “You’re a diamond in the rough.” A “cut” above the rest, if you get my drift.
1st inmate: So, do you really
1st inmate: So, do you really like to enter cartoon caption
contests?
2nd inmate: Yes, the contests are “free,” and I want to be
free. Besides, I am trying to learn to spell
words and use good grammar. A much better way
to impress people than using a gun or knife.
1st inmate: How many cartoon
1st inmate: How many cartoon captions can you enter per
contest?
2nd inmate: For the Eli Stein contests, he encourages
multiple entries. So, it’s like playing the
lottery, where maybe one entry will win. Maybe
he will put in a good word to my parole board.
“Wanna watch Shawshank again?
“Wanna watch Shawshank again?”
So, what’s new?
So, what’s new?