Over the 5 years I delivered pizza, I collected a few memorable experiences. Maybe not on the level of others here, but I’ll share them anyways.

1. Delivering to the copper mine. Technically, it was outside of our delivery area, but they always made large orders, and they almost always tipped well: Often over $50, once $100, almost always at least $20 except for one time when they took forever to come to the gate to meet me and still only gave me $10.
2. Once delivered a response to a prom invitation. Took a pizza with the word ‘yes’ written in pepperonis on it to some guy at work. Because the girl didn’t want the answer messed up, she asked that we not cut it. So when I got there, I took out the pizza and actually opened the box for him to show him the answer (he was understandably confused when I told him I had a pizza for him). He was rather happy about it, though I hope that he was able to find a knife somewhere to cut it.
3. Here’s one for the annoying category: people who would have their kids answer the door to get the pizza so that they could skip the tip without me having the chance to glare at them for it, or something like that. Only happened a few times, but one of them did it twice close together and were near the edge of my delivery range; since they hadn’t put ANY numbers on the credit card receipt, I gave myself a $1 tip from them. One of only 2 or 3 times I ever did that to someone.
4. I never had the experience of someone opening the door naked, but I had a few times where a woman would bend down to sign the credit card receipt on her leg and give me a very good view down her shirt. It was really awkward the one time it happened with a nearly-flat teen. Also had a few with semi-transparent shirts.
5. Had the opportunity to meet the most disgusting person I’ve ever seen. Obese, though at least able to walk. Wearing sandals, which did nothing to hide her absolutely disgusting toenails (at least on the toes that still had them, one or two were gone). Fingernails weren’t much better. Missing several teeth. And her hair was an absolute rat’s nest. I’m not sure if the smell that made my stomach churn was from her breath, her BO, or just her apartment. I met a couple of men who were almost as bad, but she’s the one who stood out the most.
6. One family that we delivered to would almost always order a side of sardines. Only time we ever used the little fish, that I knew of. I’m pretty sure that they fed them to their dog.
7. Once had an order for our largest pizza with literally EVERY topping we had on it, except for anchovies. The thing ended up being at least 30 pounds (we weighed it, but it was too long ago to remember for sure). It was also near the edge of our area, and I was hoping for at least a decent tip. The guys seemed almost surprised that I even showed up (if it was a prank, you shouldn’t have given us your address and credit card) and only tipped me a dollar or two.

So, there’s my most memorable moments.