For me, this is the injection of anesthesia at my latest consultation at the dentist, it was so painful that i screamed to him. Anesthesia is rarely a time of pleasure, but damn, it has never been so painful.
I was standing in my kitchen with a chef's knife trying to work out just how to position everything. I didn't think I could get a good angle on it. Then I stopped and went to ask Wikipedia if people can live without a big toe.
Wikipedia told me that without a hallux you'll walk funny. And between having an unwillingness to walk funny and not being able to figure out how to actually take the swing, I ended up calling someone to take me to an ER.
It's a little embarrassing to be complaining so much about "Ow. My big toe hurts." but holy shit that pain is real.
My worst ever is a gout flare that I got in my knee once. That's when I discovered I don't like morphine.
But yeah, I've had sciatic issues associated with spinal disease, a three-hour tooth extraction, a section of flayed skin. All of that doesn't compare to gout.