When I was in high school I was into stretching my ears. Well me being a dumbass 16 year old kid at the time, I thought shoving a sharpie in there would taper them to a bigger size. Anyway, I ended up ripping my ear and it was the most extreme pain I've ever felt.
Also walking on a broken toe is awful. I had to limp for like 2 weeks straight lol.
One time when I was violently ill, dry heaving for 3 straight days. Also another time I fell off a trampoline and my leg got caught on the metal ring around the edge. I was just hanging there for like 10 seconds, amazingly I didn't suffer any injuries it just really hurt at the time. I've never broken a bone or had any particularly bad sprains even, not sure if that means I'm durable or if I'm just really lucky.
Also I split my head open when I was 5, but it was more scary than painful.
Fractured my L3 lumbar my senior year of football. Made a tackle and I felt a shooting pain through my entire back. Had to go through 6 months of physical therapy and wear a back brace for 4 months. **** was painful and I couldn't even do the littlest things at first. Wasn't able to bend down to tie my shoes or even put them on because my back was locked up and it hurt so bad. 3 years later and I still feel it every couple days. Can never go back to serious lifting because its something that can never 100% be fixed. Even if I go running I have to watch it because after a mile or 2 it starts to swell up so I have to stop
Hitching off the back of a car on a skateboard about 11 years ago. Friend went faster than I thought he was going to and I got the wobbles. Lost control, slid on my stomach for about 10 feet. Lots of road rash.
Also when I was like 7 or 8 I was climbing over a fence. Those ones where the fence sticks above the bar in like a v shape. My foot slipped and it went in my thigh. Had to go to emergency room to get stitches.
Burst ulcer, writhing on the floor in fetal position, a flame burning in my guts while I gasped for air...luckily, we were near an ambulance station and near a hospital, so I was being operated on within 30 minutes, which saved my life.
Days later, after days of only drops of water, I started to get seriously obsessed about something more than drops of water. I was told that I first had to "pass wind" before I could have anything more. So, eventually, on the third day after the op, I was finally able to shout, 'Hey nurse, I farted!'.
Loss of my two best friends from a car accident when I was in the 8th grade.
Physically, hard to say. Haven't broken anything (that I know of). Had Appendicitis. That sucked but I'm not sure that was worse than the time I got kicked in the balls at a Tae Kwon Do tournament by a black belt. The cup moved as I got hit because I was going for a kick at the time. He did a spinning back kick right up the alley. Was ridiculously painful.
Got my front tooth knocked out as well but I'm not sure that was as much pain.
The luckiest and unluckiest experience was my most painful, when i was in 1st or 2nd grade i slipped on a wet spot and hit my head dead on the edge of a piano bench(unlucky) split my head open and i needed stitches but it missed my left eye by about a few centimeters(lucky)
Also before i got glasses last year i had frequent migraines, like 2 or 3 a week, that **** sucked