Two games stand out. On this throwaway temporarily to talk to a friend in PM's until I can get access to my main account (HDD issue, don't know my password)
World of Warcraft
March 2005. Met my future college roommate via the universities website. We start chatting, become internet/phone bros (for lack of a better term). He says our other roommate that's already there and that he's been talking to is playing a game called "World of Warcraft". I had heard of the name Warcraft because most of my friends were obsessed with Warcraft 3, but I was too into Halo 2 and other stuff to care. He said "it's so popular they had to open new servers". He told me "you should be a Human Paladin on xx server because we're there, they can heal, and wear the best armor". I checkout screenshots of it as I literally knew nothing about it or what an MMO was except for that weird stuff some people play called Ultima Online that I saw a few screenshots of. I kid you not one of the 1-4 pics on the back of the box was a random screenshot of Gnomeregan as if that was supposed to entice you. I ordered that + FF11 from Newegg as I was a fan of FF.
Games arrived, tried FF11 first since I knew FF. I lasted about an hour in it. Tried WoW....I was captivated, everything about it was enthralling. I went from one of the most clueless players to clearing all content when it was top content (except naxx, stopped at 4HM), was one of the first people to get the Deathcharger's Reins. Was in top guilds at various times. Played that Paladin as my main from 2005 to somewhere in MoP and then went alt crazy, ended up with 12 different classes, eventually quit in WoD because what the game had become something I won't discuss here so I'll also cut the topic and ego here.
If you were on Dunemaul during classic, I might have known you.
Demon's Souls
It was around 2009, looked at an ad in the paper. Saw a few games had just gone on sale for the PS3 that I had just bought for MGS4. I said "eff it" and decided to buy the one called "Demon's Souls". Put it in, tried it, rage quit a bit after getting to the first boss and dying a bunch and making zero progress. Left it untouched for a month due to owning too many games then suddenly decided to try again. Quickly realized I was over encumbered and that's why when I rolled it resembled John Goodman full of Christmas ham trying to somersault. Beat the first boss, realized this game is great, everything about it was refreshing compared to nearly everything else. Went on to platinum the game without using either item dupes in a few months, put in several hundred hours. Also pvp'd quite a bit. This was long before barely anyone knew about it and before the servers were scheduled to be shut down. The community was amazing back then, everyone was willing to help out anyone for any reason regarding anything, everyone was kind, but they wouldn't hold your hand, you were expected to make mistakes and then improve. Then it all went to shit when the game became famous, primarily the community. I've gone on to play and enjoy every Souls game as soon as it came out and platinuming/getting every achievement for every platform it's available on, every first playthrough was done solo starting with DS 2 and 3. I enjoyed it that much (I usually don't care for trophies/achievements)
The one exception is I haven't gotten around to playing BB yet, I feel I may have waited too long and the community is dead, though I'm glad I waited due to the PS4 Pro's existence.