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(dead, via archive.org)
This is the blog of what I, wearing my very best armchair psychologist clothing, could only describe as a psychopathic, nihilistic young adult. It's quite a fascinating read despite the somewhat shocking content. A very good abyss to stare into.
Likely needing no introduction, Geocities was the foremost pioneer of free general hosting. It allowed a massive number of people to express themselves on the early Web, including myself. PageBuilder was a boon for those unwilling to manhandle bodies and anchors. Yahoo's 2009 takedown of sites using their legacy service led to a number of dead links and broken images appearing all over the Internet. Fortunately, some cyber superheroes managed to back up an impressive amount of data before the plug was pulled. A good rundown of these projects is available on the relevant Archive Team wiki page.
Microsoft's answer to AIM, ICQ and other early IMs. It overtook its competition in many parts of the globe, including my own. Over time, the protocol (MSNP) and official client grew in features, be they avatars, custom emoticons, webcam chat, games, nudges or winks. A popular addon program, Messenger Plus!, added formatting, sound emotes and a number of user conveniences, among other things. The service and its active users were slowly absorbed into Skype some time after that was purchased by Microsoft. Here are a few interesting references you may find interesting:
A (mostly Flash) game site from yesteryear. Seems to have disappeared right off the Internet, leaving very little behind other than broken links. The few relics I could find were fansites of specific games like Battlefield (example). I spent a good bit of time on there in my youth.