Free software I've been happy with

MediaMonkey - A while back I mentioned I was searching for a new music player, something that would let me shuffle through my library nicely. I tried nearly everything out there and 95% of it was awful. Media Monkey is awesome. Less bloated than iTunes, more feature-rich than Winamp, MediaMonkey has it all. I went from being bored with my massive music library to being entertained again.

Media Player Classic - Make no mistake, VLC should still be installed on every system. But Media Player Classic is a little bit more attractive and faster for jumping through certain video files.

RocketDock - This is a sexy lightweight little program launcher. I always used the built-in sidebars in XP but this is sexier.

Notepad++ - My favorite programming editor. I keep finding new features in it that make my life easier.

Pidgin - I replaced Trillian with this after being horrified by how bulky Trillian Astra looks. I still like the simplicity of Google Talk but this is cool for all the other protocols.