Ex-Cons Reveal The Craziest Thing They’ve Ever Seen In Prison

When people are found guilty of breaking the law, they’re sent to jail. In some cases, they even go to a high-security prison if the crime deserves that kind of punishment. It’s safe to say that living in jail or prison would be difficult; from the dealing with a lack of privacy and personal space to rooming with strange criminals, bad things are bound to happen…. 

Mix those bad scenarios with head-strong prison guards, terrible food, and bad weather, and you really have a recipe for some crazy things. It’s not all rule-breaking and riots; there are even stories complete with random acts like hiding underwear or even taking a chunk out of someone else’s ear. Check out these startling things prison guards and inmates have seen first-hand.

The Worst Is Not Knowing Why 

I once was just chilling at my place, and the next second, I had these marshals come and kick my door right down. After that, I ended up spending a ridiculous 36 days in jail. The worst part is that I had no clue why I was there. I ended up finding out that my discharge papers had been messed up, and I somehow got listed as AWOL….

No one at the jail could tell me anything about why I was there other than that it said “federal hold” on the papers. Some of the corrections officers at the jail even asked me if I had done some terrorist stuff. I have to say that the scariest part of this jail experience was being there and having no clue why and not even having those who run the jail know why. Reddit User: TYRwargod

One Way or Another 

I’m a corrections officer at a small to medium security facility. We had this guy who actually managed to cut his kneecap out and use it as an ashtray. That’s not even the weirdest thing he did by a long shot. A few years later, he cut a small piece of flesh off of his hip and mailed it to the state corrections commissioner….

It came with a letter stating that he was going to get out even if he had to mail himself out a piece at a time. Apparently, the commissioner really is a stickler for the rules/has a sense of humor. That inmate had a few more years added to his sentence for escape. This is technically the correct approach, since it’s considered an escape even if your pinky is outside of the fence. Reddit User: [redacted]

Making Me Paranoid

There’s one thing that’s the craziest when you’re in jail. It’s not even the things that you see people do when you’re locked up in there. The craziest thing is that people can look so normal despite what they may have done to end up in there. During my time in prison, I met serial killers, people who killed their family, and mass-murderers. 

Half of them seemed like they didn’t have a violent bone in their whole body. This has made me into a very paranoid person, especially when I’m out and about in public. I can’t walk by someone without feeling like they might be trying to kill me or might go and kill someone else at some point in their lives. I’m a work in progress, I guess. Reddit User: Dr_Weirdo

Is That the Mailman? 

When I was in a jail in New York, we’d get our mail delivered by the mailman. He would walk around with a little cart, park the cart at a corner of a block, the proceed to deliver mail for that block while leaving the cart behind the corner. My cousin and I began to ransack the mail carts while they’d be left unattended, taking everything we could carry. 

We’d take them back to my cell and go through the mail, and we’d find things like credit cards (it was a different time back then, and they were easy to use), sometimes cash, gift cards for the commissary, just things like that, and we’d split whatever we could. We did this for a couple of weeks without getting into any trouble. Reddit User: [redacted]

The Gourmet Jailhouse Nachos  

I must say that I’ve never had anything crazy happen to me during my time in jail. The craziest thing, though, was the food. The food from the jail kitchen was so awful, but you had to eat it to keep going. But this was when everyone’s creativity would take over, and we became some five-star chefs, I guess. 

The best thing was eating jailhouse-made nachos. We would ration our cheese, bacon, peppers, and meat. We would then boil it all a plastic bag that was placed in the hot water tank. You then squeezed the sauce over some Doritos from the canteen. I’m not joking when I say that these were the best nachos ever. Nowhere can compete now. Reddit User: [redacted]

Learning New Skills

It’s not a crazy story, and I wasn’t a guy who was in jail. I’m actually a lawyer now. Before I became an attorney, I did an internship with a judge. As part of this training, I ended up touring some of the federal prisons in the state. I was super impressed with how the jail was being run, and my faith in humanity was renewed. 

I guess the prisons had some sort of leather and crochet crafting available to them. They would make purses and other items that they ended up sending back home, and they were learning a skill at the same time. I have to say that some of the bags I saw even looked like designer bags. I really hope they made something of it when they got out. Reddit User: thisguy1210

One Man’s Trash

It’s not me who’s had jail experience; it’s actually my brother, and yes this is a true story. He’s serving a fair amount of time. When he first went in there, his artistic abilities, especially painting, were really at a beginner level. It’s gone from weakness to strength while he’s been in jail. From stick figures basically to truly unbelievable pieces of work…. 

I have several hanging in my house. He had access to actual paint and canvas, though, but he’s also made some really amazing things from the linings of chip bags and cigarette packs on top of colored paper: specifically flowers, crosses, baby shoes, and purses. The crazy thing is that he couldn’t do this before he was there. I’m a proud brother. Reddit User: phoenixink

The Honey Bun Hit 

So, I just got sent down the road, and it’s my third week in the lockup. Yeah, yeah, I know. Our weekly card game goes nuts as two guys move from talking badly to each other to throwing fists. Things quickly escalate, and the guards storm our area. While being locked down, one guy screams at the other….

“I’m gonna put a Honey Bun Hit on you!” I looked at my cellmate and was like, “Seriously, what kind of rubbish is this?” Turns out you can have another person stomped down for the price of 20 commissary honey buns. That’s some absolutely ridiculous gangster stuff that goes on in jail. Some people make you wonder. Reddit User: ricecrusher

What a Beautiful Day to Be in Prison 

I work at a federal penitentiary as an administrative assistant but am employed in one of the living units rather than one of the administrative buildings. This means that I’m always near the inmates at all times. This interaction took place on a warm summer day as I was walking to the unit in which I work….

An inmate came up to me and said, “Shouldn’t it be illegal to lock someone up on a day as beautiful as this?” I looked at the prisoner with a very quizzical look. I said, “I suppose you shouldn’t have committed a crime to land you in prison.” The inmate was clearly impressed by my cheeky response, and off I went about my day. Reddit User: [redacted]

Jail Turns into a Finance Session 

I was in jail for the night in a cell with six other guys. In the morning, one of them was trying to write a letter but was having some difficulty spelling some things. I helped him spell some words, he asked me what I was in for and did for a living, and we got to talking. I’m a financial advisor who used to practice as a CPA….

For the next couple of hours, it was a group personal finance session. When I was released, they told the two guards who were escorting me out to ask me about investing, and that’s when the guards also asked me for help with their 401Ks. It’s not where I expected the night to go, but I guess it could have been a lot worse. Reddit User: Athosaurus

Money Matters in Jail 

I’ve never been to state prison, just county jail. After being in that trash heap the first time, I was hoping that if I had to serve time again, it would be in prison. State prisons are run much better than county jails. Especially the one I was at. My second time there, I met a guy who had a contracting business…. 

Every day, I would meet up with him in his cell, and we’d talk money. This was back in early 2008 when the economy really started to take a dive. I became extremely interested in the stock market and the like. This guy knew a lot about it, and all he asked for in return for teaching me about it was to do the daily newspaper crossword puzzle with him. We actually had a lot of fun doing them, along with talking about business. Reddit User: monotoonz

Hidden in Plain Sight 

I used to work at the jail in TN as a nurse. For about a month straight, we kept having a bunch of inmates in a 4C coming up positive for opiates (tested because of the fact we knew they were taking something), yet they were not prescribed any. The COs did a cell search as well as a cavity search on all the inmates in that cell…. 

They couldn’t find anything. It wasn’t until two weeks later when one of the COs saw an inmate licking the “crayon” on the picture he had received from his “kid.” Turns out two of the inmates’ wives were taking pills, grinding them up, coloring them with food dye, and then using the substance to paint the coloring book pages to resemble a kid’s picture. Reddit User: [redacted]

We Won’t Regretti the Spaghetti 

This is about my dad. All the inmates, including him, had a job in prison. His first one was monitoring the thermostat with two fellow inmates. Through fierce work ethic and ambition, he worked his way up to invoicing. He had been the president of a bank, so he had the chops for it. Essentially invoicing was chock full of CFOs, executives, and CPAs….

One day an order came in from the cafeteria: 1 million pounds of canned spaghetti. One of my dad’s colleagues took the order over to the director of the invoicing dept, an individual employed by the prison. He annoyingly snapped at the guy who was formerly a “numbers guy” on the outside, “If the cafeteria places an order for spaghetti, they want the spaghetti!” Whatever you say, boss. A semi arrived with more canned spaghetti than they bargained for. Reddit User: Dubya_t

The Sassy Inmate 

My mom has been held before. She said that when she was in there, they had several women to one cell, and their cell was being punished for some reason, and they only got one square of one-ply toilet paper per person per day. So one of the ladies, a big, sassy woman, started ranting and raving over the ridiculous conditions they were being subjected to….

A guard came over, and she got into a shouting match with the guard. Well, the sassy woman wasn’t going to take any nonsense, so she decided to walk over to the sink and rip the sink clear off the freaking wall, spraying water everywhere before throwing the sink at the cell door. They ended up relocating them to another cell and taking the sassy woman off into solitary or something. Reddit User: gradual_weeaboo

Thought I Was a Goner 

I was in jail once and had some scary times in there. The one time I nearly had a heart attack. I ended up running into a guy that was busy making a shank with some plastic that he had found on the concrete behind one of the doors in prison. I made the big mistake of making eye contact with the guy….

When I did that, he smiled this crazy smile that freaked me out completely. I awkwardly just tipped my hat at him and got out of there as quickly as I could. Later on, I saw him again and thought I was a goner. He ended up giving me a candy bar as his way of thanking me for being cool about what I’d seen, so I guess it wasn’t so bad. Reddit User: badguy2

You Ain’t So Bad Yourself 

I was never a prisoner, but I was arrested 2.5 years ago. While sitting in the holding room with about 20 other guys waiting to be processed, I noticed everyone looking pretty bored and miserable. I told everybody that I knew some games we could play to pass the time. A big guy from across the holding room said, “What are you talking about?” I’ve worked at summer camps for the past 11 years and knew of a name game called “bang”….

This game works by saying someone’s name, and they duck. The two people next to them turn towards each other and hold up finger guns. Whoever says bang last dies. Another game we played was called Mafia, where someone tells a story of how a townsperson dies. The look on the guards’ faces as they were walking by and seeing a bunch of us playing games was pretty priceless. After the games, the big guy turned to me and said, “You ain’t so bad.” Reddit User: Baristaboy547

The Crisis of the Crossword 

I’ve never been to prison, but I went to county for a few days for shoplifting. I tore a section out of the newspaper to do a crossword, and another inmate asked me if I ripped up the paper before she had a chance to read it. I went, “Uhhh…” because I was a sophomore in college and she was in her late thirties….

This other inmate, in her sixties, goes, “It’s just the jobs section on the other side.” The first inmate says, “Maybe I wanted a job!” and then the person who saved my bacon says, “You aren’t getting a job, you’re in ORANGE.” The first woman slammed her cell door shut. I was in stunned silence the whole time. Let’s say that I learned my lesson. Reddit User: [redacted]

Prison Pizza Parties 

I’ve never been to prison, but my uncle has. Sometimes he shares some of the stories of his time there. The other day, he was at my house and told us that every once in a while, he got the chance to work in the kitchen there. He said that they had some really amazing ingredients in there and even made pizza….

He said that the pizza they made there was even better than the chain pizza restaurants. This was great for him, but I was actually angry at this. I was infuriated at the thought that my tax money goes to feeding these criminals pizza. And here I thought they only ate beans and other cheaply made foods. Reddit User: RicoSuave21

Being Held Against Your Will 

I was working the overnight shift in the main control room at the jail. After 11 pm, the lobby is locked, and anyone who wants to come in has to push a button that rings into the control room. I get an alert for that button. I answer the intercom and say, “Can I help you?” It’s some drunken guy….

He says that his friend was arrested earlier that night and that we’re apparently holding him against his will. I look at my sergeant, who’s sitting in the control room too. I say, “We’re holding 650 people against their will. 680 if you count the officers because, let’s face it, none of want to be here either.” Reddit User: [redacted]

Meet Battery Man  

I did one year at a federal medical center. It was an easy time served in there, and as an FMC, we tended to have those who didn’t fit in at other places. The oddest person there was nicknamed “Battery Man.” As far as I know, he was excused from work detail and spent his time circulating the dorm with an AA battery that he would hold up against the wall….

He would then breathe in deeply with his eyes closed and hum. He believed he was cleansing the building of evil. I never found out what he did with the batteries; was it the same ones for the whole year? Did they fill up or something? Reddit User: mythrowawaymine

Crazy to Get Out of General Population

My cousin is a CO at a state prison. He told me that some guys act crazy just to get out of the general population, but some are actually insane. They had one prisoner who had pica. He would eat so many dangerous things that he would need surgery weekly. He had his stomach cut open so often that the surgeons installed a temporary zipper mechanism on his abdomen for easier access….

The man managed to get out of his restraints and undid the zipper. The CO on duty went to check on him, and he was playing with his small intestines. Also, he told me that some of the sickest criminals don’t look like you’d expect. That creeper in the corner might be in for writing bad checks, but that old guy with a cane and a limp killed 6 people. Reddit User: [redacted]

The Most Creative Drop-Off 

There are two small prisons on the outskirts of our little town; one sits right beside the road, and the other you have to drive a half-mile down a dead-end road to get to in the dense woods. People will “accidentally” stumble upon the second prison and “lose” their drugs and phones. In the middle of broad daylight, these two guys decide to play football in the woods….

Then “accidentally” throw their football over the fence. Once the ball flies over the barbed wire, they take off running back into the woods while the guards call deputies to the scene. The ball is intercepted by the guards, who realize the ball is actually being held together by duct tape. When they open it up, it’s full to the brim with drugs, pills, and cellphones. Reddit User: [redacted]

We Need a Medic in Here  

I was in jail once upon a time. The time in prison wasn’t so bad, except for this one time. I was just sitting there talking to a friend, and then he ended up getting up and leaving. A couple of minutes later, this guy ended up falling over and out of his seat. The unit went into lockdown after that…. 

It then took about thirty or so minutes before the medics actually showed up. This guy who I had been chatting to had died of a stroke, and I was the last one to talk to him. After that, the place felt pretty creepy and felt like we had a ghost in there with us. Nothing the medics could have done, but still scary to see. Reddit User: anon1moos

A Little Extra Outside Time 

There was a riot during an inmate organized and superintendent approved soccer championship game when I was in prison. I somehow was the only white guy on the Jamaican team, and still, to this day, I think that worked to my benefit that day in prison. However, truth be told, what ended up happening was a full-on riot instead of soccer…. 

The riot turned into one side against the other, and both sides just left me alone. Another benefit was that yard time was extended by a couple of hours due to the fact that we all had to lie on the ground for a few hours. I know it wasn’t ideal conditions, but you’ll take what you can get when there’s a chance for some extra time outside. What a day; I’ll never forget it, I don’t think. May have even gotten a sunburn. Reddit User: UndercoverEmbryo

This Wasn’t April Fools 

The guards did some pretty mean things when I was in prison. This time it wasn’t a physical thing, but I just felt so bad for the guy that it happened to. I remember the guards convinced this one guy that he was getting out a week early because his release date was a holiday. The guy was just so happy about this news….

He was so happy that he was actually scrubbing his walls and mattress and bragging about being home for Thanksgiving. He ended up snapping when he learned it was a joke. This then meant that his stay got extended because he ended up beating up some guy because he was so mad about the joke they’d played on him. Reddit User: SamManilla

Living Like a Jail King 

So, in my story, my father actually went to jail rather than prison, as he was misidentified as someone who robbed a store recently. He was only there for about two days before having to be bailed, but he sort of lived like a king during his accidental time in jail. He has diabetes, so the guards had to give him proper food….

This was stuff like omelets and muffins, while the other prisoners usually got tiny bowls of cereal with a small carton of milk. Even at dinner, he got steak with veggies while the others got sandwiches. The others were so desperate to get his food that one guy specifically asked for some of my dad’s food for a month’s worth of shaving razors. Reddit User: TheGuestAccess

The Hazardous Cloud Cover 

One of the oddest things I saw behind bars was the guards in HMP Parkhurst canceling the prisoners’ time in the yard because there was a cloud in the sky above it. Yeah, I know it sounds pretty crazy, right? But there’s some type of rule behind it. I guess according to the prison authorities’ logic, rain means wet ground, which constitutes a breach of health and safety…. 

A cloud suggested that rain could have been on its way, and they wanted to be proactive and deal with the threat before it arrived. Considering the nature of prison, I wouldn’t have thought a cloud featured at the top of the list of things that could have potentially caused us harm. But who am I to comment on that, I’m just an ex-convict. Reddit User: [redacted]

His Lips Are Sealed 

My mom is a nurse at the county jail. A young kid, 20 or so, is about 10 months into an 18-month sentence for hacking a bank and stealing 12 million dollars. Computer crime laws aren’t written very well, and good lawyers can get most crimes reduced to the general “did something naughty with a computer” in the cover-all Fraud and Abuse Act of 1986.

Every week, the FBI comes to talk to him. They want him to tell them where the money is and then say they’ll let him go. He’s content just to do his 18 months and be rich. My mom says, “He’s the nicest prisoner.” Bonus from my mom: she said, “You know, if you applied yourself, you could do something like that.” Thanks, mom. Reddit User: dystopianview

Something Out of a Sitcom

I once knocked a policeman’s helmet off with an adult toy while wearing nothing but a French maid’s outfit. It was a bachelor party and I was in the least humiliating costume. They chased me, tackled me, we all fell over in a bundle, and the same policeman ended being squashed underneath me. He wasn’t happy. I spent the night in the cells. I never got charged, but the other policemen made me retell the story about 30 times.

Side note: I walked into the holding area in cuffs, and the guy behind the counter was in my class in school. He did that thing people do in bad sitcoms where they’re drinking and they laugh and spit a mist of liquid. I didn’t think people actually did that. That’s my craziest story of something that happened in jail or more something crazy to land me in jail. Reddit User: Booster21

So Much for Having My Back 

No clue exactly what happened; the details from that night are still pretty blurry. So this won’t be a story of the craziest thing that has happened in jail, but I think it’s a crazy story about how I somehow ended up in there. To start the story off, my brother and I once woke up in a cell. We were wondering how we got there….

We had apparently ripped a branch off a tree in the middle of town. We then went to court a week later, and our drunken police statements were read out to us. Mine said that I was trying to get a flower for my brother to give to his girlfriend. My brother’s said, “My brother got me into trouble and that’s why I’m here.” Thanks, bro. Reddit User: JamieThinker

Solving the Prison’s Problem 

I was in this little one-horse town, and while I was being booked, the system crashed. The 20-year-old who was booking me freaked out; it was, of course, 3:00 am, so there wasn’t anyone he could call. I walked him through fixing it, all the while handcuffed to a row of chairs. After an hour or so, he let me stand next to him at the computer and fix the problem….

It was actually kind of fun and gave me quite the story to tell when I left that place. After I ended up solving the problem, I had to remind him to change all of the passwords when I left. I doubt he ever did change those passwords, but I’m never going back there again, so the poor guy doesn’t need to worry about it too much. Reddit User: SameOld_SameOld

Walking Under the Influence 

I haven’t been to jail, but my husband has before we got together; we were just friends then. He got stopped for “walking under the influence (WUI),” so they took him to jail. He spent one night in jail, and then every court appearance he made after that, they kept delaying his appearance because they knew the deputy had done something very stupid….

There was a personal issue the cop had with my husband involving one of his ex-girlfriends. The funny part of the story is that the day of the very last court appearance, the judge asked my husband if he had anything to say, and my husband said, “Yeah…I promise never to try to walk home drunk again; from now on, I’ll drive!” The case was dismissed. Reddit User: [redacted]

The Murderesses of Holloway 

I spent two weeks in Holloway and two weeks in Cookham Wood High Security. I was sitting around at my job, which was sewing tracksuits, one day with a group of women I was “friendly” with. I didn’t realize it at that time, but the whole group was in for murder except for me. One of them began talking about killing her husband and the mistakes she made in a Captain Quint of Jaws sort of way…. 

She began by saying, “If you’re gonna chop ‘em up….” And they all responded, as one, in unison, I swear to God, “You’ve gotta freeze ‘em first.” Hilarity ensued after this woman’s comment. It then hit me that I was the only non-murderer present. I was speechless with the uniqueness of the moment I found myself in. Reddit User: [redacted]

Forget Me Not 

I spent time in four different jails within 48 hours. Yes, that’s crazy in itself. First off, I had to sleep outside in tents; I then had to go to the bathroom in the toilet/drinking fountain/sink combo while people slept right under it. I then had to eat nasty green meat and slop. It’s basically chopped liver, water, and some added nasty stuff….

While I was there, I tried my best not to go crazy. I don’t know how people stay there for any longer than I did. The crazy thing is that I was actually only supposed to spend a total of 24 hours in the place, but it turns out that the guards “forgot” about me. They’re seriously such idiots, and I was so angry when I was finally released. Reddit User: AndroidHelp

Pulling Your Leg on This One  

My dad has been a prison officer for most of his career, so the stories he comes home with are just insane half the time. This one was pretty funny in the end, though; well, maybe not for the officer involved, but definitely for us around the dinner table. The one time, he had to get the help of other officers to restrain an inmate….

The inmate was lashing out, and that was why they needed to restrain him in the first place. Unfortunately, one of the officers who was busy trying to help out with what was going on didn’t know that this particular inmate actually had a fake prosthetic leg. He ended up pulling the leg right off and also fainted. Reddit User: iEuphemia

The Legend of Mrs. Puff  

I worked in a women’s prison, and I saw a lot of colorful characters, but one stood out. She wasn’t the type you’d expect to be in prison: very mild-mannered, even seemed a little happy to be in prison, away from her old life. She just wanted to do her time and leave. It always made me pleased to see inmates like this.

Then she started acting oddly, like talking to inanimate objects, yelling at them sometimes. She claimed she heard rocks talking to her, then the food, then coat hangers. She attacked two guards one night, thinking they were the voices talking to her. She got put in solitary, and from what I heard, she went insane. I’ll always remember Mrs. Puff. Reddit User: ReferencesCartoons

The Wrong End of the Stick 

The prison guards in HMP Albany dug up the body of my dead pet budgie, thinking I’d buried contraband. People serving long sentences were allowed to have budgies, and I’d come to see mine as almost like my child. There was a little grassy area with a tree on it outside the wing, which I’d decided was a suitable spot for a burial…. 

About 20 minutes later, I was looking out my cell window when I noticed a group of screws walking towards the grass. They must have seen me burying something and got the wrong end of the stick. They eventually uncovered the budgie and had a good laugh about it. I didn’t see the funny side, though. Reddit User: [redacted]

Time to Wear the Mong 

I had a short guy bunking with me. He wasn’t a dwarf, just really short. He made a thong out of a t-shirt and would wear it around when new guys showed up to mess with them. He’d walk up to their cells wrapped in a blanket like he was cold, then take it off and kind of pose a little before he started talking to them…. 

He called it a “mong” because it was a man thong. Sometimes he’d walk into someone’s cell and crawl into the bunk with them while they were sleeping for a brief second before he jumped up, saying, “Oh sorry, this isn’t my bunk!” That was a really funny form of initiation in the prison that everyone could appreciate. Reddit User: bunzablaze1990

Hidden Underneath Was the Thief 

This one inmate was strip-searched and revealed to be wearing a pair of Anne Summers-style knickers. They searched his cell and found four other similar pairs. They wanted to know what was going on and fired off questions at him: “What’s going on here? Is there a black market in knickers? Where did you get them?”

He refused to answer, so he was hauled in front of the governor for having unauthorized items in his cell. I later heard that the governor had read out the charges, and then asked him if he had anything else to say. “Yes,” said the undie thief. “I’m very sorry sir, but they’re your wife’s knickers.” He had been allowed outside the prison to paint the governor’s house, as he was a trusted inmate, and had snuck inside and stole the underwear. Reddit User: [redacted]