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Let's see, the Nintendo Nsider forums before everything went stupidly child friendly at Nintendo. I blame Reggie, personally for pulling the plug. All that remains of my membership there is my embarrassing username and the fact that I trolled myself off the tech support forum.

Team Rocket's Rockin was one of the first forums I recall attending. I forget the why of why I joined.

The Cave of the Dragonflies, a more friendly and personal place than say the likes of Seribii. I was a pokemon fan at one point, could you tell?

Paranoia Live, a website for the Paranoia RPG, but the community sadly dried up and died out.

Thinkgeek. It was a place for nerdy stuff, then the content went downhill, and then they were bought out by GameStop. (I'm looking for a replacement to this one.)

Hey, remember those sites from pre-2000 with the midis and nearly endless pages of smilies that sometimes told a story?

Oh, another chime for Cracked. Used to be funny, and now it's just 'eeeh.'

This one is going to rub people the wrong way, but I long ago abandoned Winamp for Foobar2000.

RCT-FUN. Some of the best parks I had ever seen in the Roller Coaster Tycoon series came from that site.

Wonka.com, before the brand was fully cannibalized by Nestle. I used to play the flash games all the time there.
The "Strange Foreign Objects Found in Dog Feces" website vanished from the Internet about 15 years ago, with only faint hints that it ever existed left online such as dead web links. Even the Internet archive has no record of it anymore.

This is such a great loss to our global Internet culture.
Winamp had a complete breakdown and died on me. VLC now, it also handily plays all zone DVD's and has a bunch of audio options. Bye-bye winamp you piece of junk.