WEB PLACES:
Download.com
Amazing site with all the freeware and shareware programs. Helps keep us up to date with the newest (and not so new) products.
Project Galactic Guide
A "Hitchhikers Guide to the Galaxy" tribute. People have sent in articles to be included, fiction and non-fiction. Most in the style of Douglas Adams.
Search Watchers
This may scare you a bit. These are online readouts of what people are typing into the search engines. Interesting to see what people are looking for, well... sometimes.

UTILITIES:
Go!zilla
Great program for downloading. Not just another download resumer, it even searches the FTP sites ensuring the fastest download possible! Can even integrate with browser clicks.
Winzip
The best compression tool I've ever used. Forget all the clones out there. This one has the best layout and the easiest controls of them all.
ACDsee
If you deal with graphics files, this is the program for you. Truly the quickest way to preview any picture or animation. Supports danged near all formats, and allows thumbnail browsing for quick finds in jpeg jungles. (corny!)
Web Ferret
Runs searches on multiple engines at once, giving you one big list of results.

MULTIMEDIA:
Real Player
A must have for streaming audio and video. Lots of music and TV sites make sample files in this format, so it's good to have.
VivoActive Player
A streaming movie player, includes sound. Almost always higher quality movies than real player ones, but isn't usually exactly streaming.
Spinner Plus
I hate the radio. Luckily there's spinner, a program that allows you to listen to music by genre after a quick signup at their site. Usually commercial free, with a huge selection of music, not the same songs over and over.
Winamp
Plays mp3 files, yay!

CHAT:
Onlive! Traveller
Fun mic chat with a 3d avatar. You get to float through 3d worlds and meet people. Allows short text messages, but mic is more fun. The avatars usually move their mouths as you talk, and can be coloured to your liking. Note: Onlive no longer supports Traveller, so go here for a list of rooms.
ICQ
I doubt anyone hasn't heard of this, but you never know. It lets you know when your friends are online, and lets you chat.
Powwow
Add some microphone chat, a whiteboard and some games, otherwise you have another ICQ clone.
VPlaces
Fun text chat program in which you use a graphic avatar and text comes out in talk bubbles. Also uses gestures, which can be animated with sound. If you have ever talked on the Excite chat servers, you're been in VP territory, but you look like a stupid mug to us. >:)
mIRC
The standard no frills text chat. A bit confusing if you're new to it.