Hottest thing I ever ate were these hot wings at a bar I used to frequent. They were made with a combination of ghost chili puree and habanero extract. I took exactly one bite on a dare before I was crying like a little bitch.
There was a Thai place I used to frequent, I've since moved away. I was ordering take out and so I just wanted Thai fried rice and I requested Thai spicy as I had many times before. HOLY SHIT. They took that to a level I never imagined. I couldn't even taste it at that point of spice, but I was determined to eat it. The first few bites were really good, but eventually the tears and numb tongue and screaming pain somehow diminished the experience.
I once tried to prove my masculinity to my friends when ordering vindaloo at an Indian restaurant. When they asked me for a heat level on a scale from 1-5, I asked for a 6. They fucking delivered on that front. It actually was pretty comical, I was munching away at it trying to hide my increasing discomfort at how insanely hot the food was, my friends told me my face turned bright red after a couple of bites and I was sweating pretty heavily, but my masculinity decreed I plow through that dish. My stomach hated me for that.
It was actually a meatball foot long sub a dude concocted on his own I know. It had a variety of things but the 3 things that really done me in goodin plum and proper was habernos, jerk sauce(homemade Jamaica style), and some ghost peppers. About a few inches I couldn't feel anything it was like my whole face, body was paralyzed...downed about 2 liters of ice water before I took another bite. I got about 3/4 and I was ready to tap out but I got in full Rambo mood and went with trusty friend Johnnie Walker Black...hit 6 shots and downed the rest of the sub. Everything that was paralyzed suddenly went all nuclear inside me and I thought I was having a heart attack. It wasn't thankfully one but shit my life was flashing before my eyes. I think it took about 2 hrs before I could do, drink, or anything. I know enjoy the spiciest shit but never will I go in there blind like that again without knowing what I'm eating first.