I have happy memories of WinBoard and a few friends, a 6-pack, and a lot of free time. Those were simpler times and, I think, it was harder to cheat. Now I get whupped by 1100 rated players on FICS who play like GMs and cheating is ubiquitous. Either that or I'm a really crappy player. lol.
WinBoard was good as it could be re-sized to fill the screen and all that. I hated that Yahoo interface and lost clumsy games because I couldn't figure it out. Call me old school.
I still, in my heart, prefer the simple DOS interface, or maybe the terminal in Linux, and I ain't ashamed to admit it. Garbage in, garbage out, as we used to say, and there's a lot of garbage these days.
This is mainly for "old timers" (in Internet years). Hopefully some people will have some fond memories of their experiences in the early days of online chess.
Here are some of my own thoughts.
I started playing online in the mid 1990s. ICS had just solved its timestamp issues and graphical interfaces that meshed with the telnet server programs had been instituted making blitz chess possible and reliable for most players. This also made online chess potentially profitable. ICS, a free server, became ICC, a membership server. ICC still allowed "guests" who could play for free but anonymously and with no additional benefits (they later did away with free guests). Many former ICS members were up in arms about the new pay site - a prevailing idea at the time was the the internet should be totally free - and FICS, mimicking the original ICS, was created (with many servers all over the world). That's where I came in. Telnet servers required players, if they wanted a GUI, to download a third party program such as XBoard or WinBoard. These are command driven interfaces that have a learning curve. Later, even telnet servers could be accessed using the more user-friendly web-based interfaces. Gaining the ability to play chess online back then took considerably more effort than today.
I've mentioned before that I played as a place called Chessmaster. It was operated (I think) by The Software Tool Works and the graphics were exactly like those used in the Chessmaster software of that time. This site was 20 years ahead of its time, limited mainly by one's cpu and the slow internet connections at the time. Besides the lovely graphics, one could select which windows or panes were open on your screen, you could resize them and move each one simply by dragging it. It took about 5 minutes to load, but once loaded, it worked beautifully. I don't think it had a chatting feature though. It wasn't around for long. I do remember that Chessmaster 5 or 6 came out with online capabilities and when it was released, the playing site was eliminated. It arose from the ashes a bit later as part of a multigame site, but it was garbage.
The most popular site, by far I think, was Yahoo! Chess. Yahoo served up many games, chess being just one. It was set up with "rooms," maybe a dozen, though I think the number increased over time. Each room had a limit- 100 or so - to how many people could be in each one. Once a room was full you'd have to wait until someone left in order to get in. For some reason, some rooms were popular and others not so much. Once in a room you could chat; it was all unmoderated and therefore sometimes rather unpleasant. But you could make a table with the option of having it public or invitation only. I used to use Y! Chess to play with my close friends because it was private and the graphics were very nice and worked smoothly. Yahoo also had dedicated chess forums. Although I developed some long-lasting friendships there, to be honest, the forums were unmoderated and extremely horrid at times. Like chess.com clubs, Yahoo also had clubs and I took advantage of that. I picture Yahoo as a precursor to chess.com but lacking the dedication and integrity to really take off.
Chessbase brought out PlayChess.com. I don't know what year but it was prior to chess.com. Although I have an account there, I can't recall ever having played there. There were a couple hit-and-run sites (you just play with no frills) such as Instant Chess and UChess. I also remember the World Chess Network, Kasparov Chess, Pogo, Kung-Fu Chess....I'm sure there have been others
Your turn.