So your buddy got caught doing something they shouldn’t. Now they’re sitting in a cell, bored out of their mind. What do you do? Send funny mail! Nothing helps pass time like a good laugh. Your letters can be the bright spot in their day – a little bit of the outside world sneaking in past those gray walls.
Why be boring when you can make them smile? A funny letter might be the only thing keeping them sane in there. Plus, humor is good for health! Studies show laughing can lower stress and boost the immune system. Your silly words might be the best medicine they get all week.
Funny Things to Write to Someone in Jail
Want to cheer up your jailbird friend? Here are some ideas that will have them laughing so hard the guards might check to see what’s going on.
1. Create a fake “Outside World News” update
Make up silly “breaking news” stories about your town. Tell them the local squirrels have formed a union and are on strike, refusing to collect nuts until they get better working conditions.
Everyone needs updates from home, so why not make them extra funny? You can include fake celebrity sightings in your hometown or claim that the local pizza place now requires formal evening wear for all customers.
2. Send a “Freedom Countdown” calendar
Mail them a ridiculous countdown with milestones like “Only 243 more prison meals to go!” or “Just 42 more awful showers until freedom!”
The passage of time feels different when locked up. By marking it with funny observations, you help them see progress in a way that makes them laugh instead of sigh. Add silly holidays like “National Talk Like a Pirate in the Mess Hall Day.”
3. Draw terrible stick figure comics about their daily life
Make a short comic strip showing what you think their jail routine looks like, but with funny twists. Draw them befriending a tough cellmate who turns out to be scared of spiders.
Bad art is often funnier than good art. Your stick figures with speech bubbles will give them something to show others and laugh about. The worse you are at drawing, the better the comedy value!
4. Write a list of new skills they’re probably learning
List hilarious “skills” they’re gaining like “advanced toilet paper conservation” or “how to make friends with people you’d normally avoid at all costs.”
Finding humor in the situation helps them feel less like they’re wasting time. Point out how these “skills” might come in handy later – like being able to sleep through any noise or eating meals in under three minutes.
5. Send fake prison Yelp reviews
Write mock reviews of the “amenities” as if jail were a hotel. “The metal toilets lack privacy but have excellent acoustics. The mattresses are… present. Two stars.”
Treating something serious with the format of something trivial creates instant comedy. You can rate different aspects of prison life like the “decor” (cinder block chic), the “dining options” (mystery meat Mondays), and the “staff attentiveness” (perhaps too attentive).
6. Make up weird prison slang
Invent ridiculous prison terms and use them casually in your letters. “Hope you’re avoiding the snorklewamps and getting extra pudding cups at the feed trough!”
Nonsense words used confidently are always funny. Explain what each term means in equally absurd ways. Tell them to use your made-up slang with new inmates to see their confused faces.
7. Write letters from their pets
Send messages “written” by their dog, cat, or goldfish with animal concerns. “Human, the food bowl was empty for FIVE WHOLE MINUTES today. This is abuse. Also, I ate your shoes.”
Pets have simple, self-centered worldviews that are funny when spelled out. Their pet might “write” about how they’ve taken over the human’s bed or how the vacuum cleaner remains their sworn enemy.
8. Share fake inspirational prison quotes
Make up “inspirational quotes” from famous people about prison life. “When life gives you prison time, make prison lemonade – Warren Buffett”
Mixing the format of cheesy inspirations with prison reality creates good comedy. You can attribute completely made-up sayings to celebrities, historical figures, or even cartoon characters for extra laughs.
9. Send “What I think you’re doing vs. what you’re actually doing” comparisons
Create funny side-by-side descriptions. “What I imagine: You planning a daring escape. What you’re actually doing: Trying to trade your dessert for extra socks.”
Expectations versus reality is a classic comedy format. The bigger the gap between the dramatic version and the mundane truth, the funnier it gets. This helps them laugh at the daily routines that might otherwise feel tedious.
10. Write jail-themed parodies of famous songs
Rewrite lyrics to well-known songs with a prison twist. “Hotel California” becomes “Hotel County Jail” with lines about checkout times being delayed by several months.
Song parodies are fun because they get stuck in the head. Your friend might find themselves humming your silly versions, which brings repeated moments of amusement. Keep the parodies light and focused on jail annoyances rather than serious issues.
11. Create a fictional jail economy report
Write up a funny “market analysis” of the prison economy. “Ramen prices stable this quarter. Cigarette values dropping due to increased supply. Invest in clean socks now!”
Economic reports are usually boring, which makes the prison version extra funny. You can include “stock tips” about which commissary items will increase in value and “market forecasts” for the coming month.
12. Send absurd “escape plans”
Draw ridiculous, impossible escape schemes using items like spoons, soap, and dental floss. Label each step with deadpan serious instructions.
The humor comes from how obviously terrible and impractical these plans are. Make them increasingly absurd, like step 6 involving trained squirrels or step 8 requiring underwater breathing for exactly 17 minutes.
13. Make a “pros and cons” list about jail
Create a list where the “pros” are absurdly minor things like “consistent meal schedule” and “no telemarketers call you.” The cons can be understated obvious things like “orange isn’t really your color.”
Finding tiny silver linings in a tough situation shows resilience through humor. This list format lets you acknowledge the reality while still keeping things light. The more trivial the “pros,” the funnier the contrast.
14. Write a letter as a time traveler from the future
Send a message as if you’re them from the future, giving weird warnings and advice. “Don’t eat the meatloaf on Tuesday. Trust me on this one.”
Time travel creates instant comedy possibilities. You can reference inside jokes as if they haven’t happened yet or mention strange events that will supposedly happen in the prison. The more specific and bizarre your predictions, the better.
15. Send jail-themed “Mad Libs”
Create Mad Libs stories about prison life with blanks for nouns, verbs, and adjectives. Include a second copy filled in with the most ridiculous words you can think of.
Word games help pass time, and the results are usually hilarious. This gives them something interactive to do and share with others. You can base your stories on real experiences they’ve mentioned, making the funny versions even more meaningful.
16. Make fake “prison life hacks”
Write up useless “life hacks” for jail problems. “Can’t sleep because of snoring? Try stuffing your ears with mystery meat from dinner.”
Life hacks that solve small problems in complicated ways are funny by nature. Make your hacks sound helpful but be completely impractical or solve tiny inconveniences with elaborate solutions.
17. Create “missed connection” ads about prison moments
Write fake Craigslist-style “missed connection” posts about mundane prison interactions. “You: guard doing cell check. Me: pretending to be asleep. Our eyes met when you shined that flashlight…”
This format works because it applies romantic longing to completely unromantic situations. The contrast between the flowery language of missed connections and the institutional setting creates instant comedy.
18. Send a “prison fashion review”
Write up a fashion critique of orange jumpsuits and slip-on shoes as if covering Milan Fashion Week. “This season’s jumpsuits feature a relaxed fit and pair splendidly with state-issued canvas shoes.”
Taking something utilitarian and discussing it as high fashion is inherently funny. You can rate different prison uniform elements, suggest “accessorizing” with commissary items, and predict next season’s “trends” in correctional wear.
19. Make a “sounds of prison” playlist
Create a fake mixtape list with song titles based on prison noises. Tracks include “Midnight Cell Door Symphony” and “The Snoring Cellmate Blues (Extended Remix).”
Everyone relates to music, and this puts a funny spin on the noises they have to endure. You can add fake reviews for each “track” and note which ones are “climbing the cell block charts” this week.
20. Write letters from a jail groupie
Pretend to be an obsessed fan who thinks being in jail makes them cool and edgy. “Your mug shot is now my phone background. So brooding!”
The idea of someone being impressed by jail time is absurd, which makes it funny. This character can misinterpret every normal jail activity as something glamorous and exciting, creating comedy through their clueless enthusiasm.
21. Send “alternative uses” for prison items
List creative, silly uses for standard jail items. “Toilet paper: also works as origami material, emergency pillow stuffing, and formal dinner napkins when visitors come.”
Finding new purposes for limited resources is something inmates actually do, but taking it to absurd extremes makes it funny. This acknowledges their limited options while finding humor in making the most of what’s available.
22. Create a fake prison suggestion box
Write up a list of “suggestions” you’ve submitted to improve the facility. “Request: Hot stone massage options during recreation time. Status: Pending.”
Treating a prison like a hotel or resort with customer service creates an amusing contrast. Your suggestions should start somewhat reasonable and get increasingly outlandish, as if you don’t understand the purpose of prisons at all.
23. Send prison crossword puzzles
Make simple crosswords where all the answers are jokes about their situation. Clues like “What you did to get caught” with the answer being “EVERYTHING.”
Games help pass time, and personalized ones show extra effort. The clues and answers can reference inside jokes between you, making it both entertaining and meaningful as a reminder of your shared history and friendship.
24. Write “corrections” to their letters
Reply to their letters with fake editing marks, circling grammar mistakes and adding funny comments like “Your description of cafeteria food was too positive. See me after class.”
Playing teacher with their letters creates a silly power dynamic that’s the opposite of the control they’re under in jail. This works especially well if you highlight perfectly fine sentences and claim they need work for absurd reasons.
25. Send a “cellmate zodiac” chart
Create a fake astrology guide that classifies different types of cellmates. “If your bunkie is a Taurus, expect them to hoard all the good commissary snacks.”
Astrology is popular because it’s fun to see yourself in descriptions. This jail version lets them laugh about the personalities they encounter daily. You can include “compatibility charts” for different prison jobs or activities.
26. Make “prison recipes” with fancy descriptions
Write up basic jail food combinations as if they’re gourmet meals. “Ramen à la Commissary: Instant noodles delicately crushed and infused with crushed Doritos, served in a plastic container.”
Food is a universal topic, and pretending simple combinations are fancy dishes is always funny. Using overly elaborate culinary language for things made with limited ingredients and microwave access highlights the contrast in a humorous way.
27. Send paper versions of mobile games
Create simple paper versions of popular phone games like “Angry Cellmates” or “Candy Crush: Commissary Edition” with basic rules they can play.
Games provide distraction, and the low-tech versions of high-tech games are funny by nature. This gives them something interactive while poking fun at their lack of technology access in a way that provides actual entertainment.
28. Write a “day in the life” from an outside object’s perspective
Narrate a typical day from the viewpoint of something in the prison, like a security camera or lunch tray. “8 AM: Here come the humans again. Why do they always look so grumpy without coffee?”
Shifting perspective to inanimate objects creates instant humor. Objects have simple concerns and observations, which when applied to prison life creates amusing commentary. The security camera might “complain” about having to watch the same boring routines day after day.
29. Create a fake prison tourist brochure
Design a travel guide describing jail as if it’s a vacation destination. “Visit scenic Cell Block D! Enjoy all-inclusive meals and 24-hour security in this gated community!”
Travel brochures are always overly positive, which makes this format perfect for finding humor in a tough situation. Describing standard jail features as amenities (like “wake-up service” for morning count) creates funny contrasts with reality.
30. Send “prison superlatives” awards
Make certificate-style awards for silly jail achievements like “Most Creative Use of Toilet Paper” or “Fastest Commissary Shopper.”
Everyone likes being recognized, even for silly things. These mock awards acknowledge the small victories of daily jail life while poking gentle fun at the situation. You can even create entire award categories like “Cafeteria Survival Skills” or “Shower Speed Records.”
Wrapping Up
Your letters can bring brightness to a dark place. When you make someone laugh behind bars, you’re giving them a mental break from their surroundings. That’s a pretty big gift! So grab a pen and get silly – your words matter more than you know.
Don’t worry about being too funny or trying too hard. Just write from the heart with a smile on your face. The effort alone shows you care. And isn’t that the whole point? To let them know they’re not forgotten, that they still matter, and that you can’t wait to laugh together in person again.