Contest No. 237 starts right now.
Here are the details: I’ll supply a drawing of one of my old cartoons that has never been published, leaving off my caption. You are invited to supply your funniest captions. To enter, simply (1) click on “See Comments and Add Your Own”. Then (2) scroll down past any other submitted captions and type your name and your caption in the spaces provided. Then (3) click “Save”. There is no charge to submit captions, and the only prize is the honor of being one of the funniest people around.
Your caption (or captions) will be posted after I review your submission. However, no captions at all will be posted for the first few days of each contest. This will 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, gut-instinct caption. Every posted caption has an indication of the date and time it was received. This is an equal opportunity contest!
There is no limit on the number of captions you may enter, but I will only post and consider the first 15 captions from any contestant. Entries will be accepted and posted for one week, after which the winning caption will be announced and printed and I will also reveal my original caption. I am the sole judge and the winning caption will be the one I deem to be the funniest one submitted (not necessarily the one that matches or comes closest to my original caption).
The cut-off time and date for you to send in your captions is midnight Wednesday, April 8, 2026.
Below is the drawing that needs your funny captions. Good luck, Captioneers!
69 Comments
I’ve already given you the shirt off my back.
“Miss Hathaway, April Fools’ Day is over—give me back my clothes!”
“Someone took my clothes and left a ransom note—call the fashion police!”
“I fell asleep—did a well-dressed but doubly-dressed man come and go?”
“Cancel my appointments—unless they’re here for Streakers Anonymous.”
“It looks like Jack the Stripper has struck again.”
“Judy, if you love my new clothes, why do you wish to work remotely?”
“Helen, see if there’s someone who’ll give me the shirt off their back.”
“Susie, I’m having that nightmare again. Care to join me?”
“Whose idea was plastic on the seats?”
“Priscilla, you’re quitting? But I told you about Very Casual Fridays.”
“I include it with my tax return to show the I.R.S.that they are taking me to the cleaners.”
“Meeting in ten minutes. Come as you are.”
“We already have casual Friday so I decided to add Get to know your Co-worker Monday.”
“Miss Stevens, is my ‘Naked and Afraid’ audition on my schedule?”
“Doris! . . . please stop telling clients that ‘I’ll give them the shirt off my back’!”
“Doris! . . . you gotta stop telling people that ‘I’d give a stranger the shirt off my back!”
“This is not what I had in mind when I said ‘we should make Casual Friday more casual’.”
“I need you to clarify the company’s policy on low hanging fruit.”
“Let Finance know that the Jenkins report has been fleshed out.”
“I resent being called a micro-manager.”
“Let’s run it up the flag pole and see who salutes it.”
“We need to improve the backend experience.”
“Send a memo that there will be no more cracks about our bottomline.”
“Our finances have reached obscene levels of exposure.”
“I need to win this suit or I’ll lose my coverage.”
“It says right here: casual Friday starts today!”
“You were supposed to pick up my dry cleaning before my 10 o’clock!”
“My wife and kid are here? But I thought tomorrow is Bring Your Daughter to Work Day!”
“I want to show the audit team that I have nothing to hide.”
“Doris . . . I need you to contact the new office cleaning service and make sure they understand that cleaning the clothes that I’m wearing is not part of their job description!”
Well then stop trying to reach me about my car’s extended warranty!
Please refrain from using pneumonic, psoriasis, and pterodactyl in your phonetic spellings.
“Yes, I know today is Secretary’s Day, and I’m waiting to salute you.”
“The entire office complained to HR? Do they know I’m head of HR?”
“I’m working late tonight—I got a little behind today.”
“Business may be down but everything else is up.”
“Tell Legal that nowhere in the handbook is ‘Casual’ explicitly defined!”
“Got your note—sorry, but as CEO, I’m very comfortable in my own skin.”
“I rushed out of the house without my briefcase, Rebecca. I feel naked without it.”
“I’m making a change to our casual Friday policy, Annie.”
“Oh, I forgot about that appointment. I’ve been very forgetful, lately.”
“I told the two little old ladies that just left that ‘I would give anyone the shirt of my back’, so they took it!”
“Doris are you sure this will help me get the sales listing for the hundred acre ‘Sunny Day Nudist Camp Property’?”
“Doris, if you don’t bring my clothes back I’ll never play lunch hour poker with you again!”
“Since I’m moving to ‘Sunnycheeks Naturalist Camp’ should I send out ‘Change of Undress Notices’?”
“Miss Jones, would you kindly go to the office supply store and see if they have a heated office chair?”
“Would you please come back in and play a few hands of get dressed poker?”
“If you play along we may be able to land the ‘Sunny Cheeks Nudist Camp’ account!”
“Before you come in . . . are you familiar with the term ‘shrinkage’ and how cold directly relates to it?”
“Please tell the President his new suit looks better on him.”
“Did you find a soft tip spatula yet?”
“If maintenance doesn’t fix the air conditioner immediately, I will be leaving my door open.”
“Did you get that estimate for a skin graft?”
I’ve got plenty of nuttin, and nuttin is all you’re gonna get.
“Bring me my long red tie.”
“Doris, I think last night I might have had that realistic dream about being naked at school again?”
“Please find ‘SPF Level 80’ Sunscreen and have two gallons shipped to me at, ‘Sunny Days Nudist Farm’?”
“Doris, I need you to bring me the biggest leaf from the potted plant in the lobby . . . on second thought if you’re wearing your tight blue jeans today you’d better bring the whole potted plant!”
“Hold my calls, Martha. I have an obscene amount of work to do.”
“This sales report is discouraging. Oh, well, I guess I’ll just have to grin and ‘bare’ it.”
“Looks like I failed my audition for Naked and Afraid.”
“Ms. Jones, what does this note mean, ‘Come quick, we need a laugh’?”
“Ms. Jones, am I in the office wearing no clothes, or am I in my worst nightmare?”
“Ms. Jones, why are the office uniform costs still going up?”
“Ms. Jones, why am I being called in to HR?”
“I’m too sexy for my shirt.”
“Paula, please remove ‘make a million dollars playing online strip poker’ from the ‘ways to get rich quick’ list”.
“To all my clients who received my earlier video message, let me assure you that it was sent in error, particularly the 3D component.”