Internet trolls, what's your worst troll that made you feel terrible afterwards?

When I was in high school, a friend and I created a fictitious MySpace profile to troll the rapidly-increasing population of super dramatic emo kids classmates. My character was purportedly a 16-year-old dude from California who wore eyeliner, wrote poetry, and was guitarist in a screamo band, moving to my hometown from California because his parents broke up. All the right things to fit in. At first, we were doing this just to get a kick out of responses to really outlandish, caricaturesque posts, but eventually this became full on messaging conversations with people about their feelings and such. It was kind of weird, but sort of exciting to think that people actually believed our character was real, so we just kept on with it, probably for 6 months. Eventually we got tired of it, but people started asking when he was moving, that they couldn't wait to meet him, etc, and we weren't really sure what to do.

I played sports at the time and had this douchey upperclassman on my team who talking down to a lot of younger players and was quite full of himself. He was taking a lot of mirror selfies of his swooping hair and trending towards being super dramatic emo kid, so we decided that my character was finally moving... and having a housewarming band party... at the douchey upperclassman's place.

We spent a few nights sending messages to people about it, hyping up the move, and eventually sent out an invitation with the date, time, and douchey upperclassman's home address and phone number. We instructing people to just go to the front and ring the doorbell. Day of, we left balloons outside his mailbox in the driveway, and made a number of prank calls to his house, asking if the party was still on. Eventually his dad picked up the phone, and yelled at us, saying that this wasn't funny and that we should be ashamed. Lots of angry messages that day and the next about trust, lies, being fake, etc, and my character eventually got reported and the profile deleted from MySpace.

At first we tried to laugh off the aftermath, but I felt terrible for abusing peoples' trust. Most pranks are probably quick, harmless, one-time things, but this ended up going on for way too long to be funny. Looking back at it now, I'm not sure if I was an internet troll or a sociopathic cyberbully.

/r/AskReddit Thread