List is a bit of a disaster, but I will get it fixed up in the next couple of days. 

This is an update and refactoring of my big software list for Windows.  Now I will offer a couple options for a few categories, as well as add a few new categories all together.  All the software unless otherwise marked is free (as in beer, sometimes as in speech).

The organization of this list will be a bit different now, as I am using external tools to help you quickly get up and running with these apps.  I absolutely love Ninite, so if you want to get a jump-start, use this

Ninite Package

(contains: Runtimes for Flash, Air, Java, Silverlight and .NET (not on apps list), Chrome, Firefox, Skype, Pidgin, Thunderbird, VLC, Audacity, Paint.NET, Picasa, OpenOffice, SumatraPDF, Microsoft Essentials, Steam, KeePass, Inkscape, uTorrent, Dropbox, Everything, TeamViewer, ImgBurn, Evernote, CCCleaner, Defraggler, Teracopy, TrueCrypt, Launchy, WinSCP, Putty and Notepad++).  

Two other things, the first is you will notice I removed all the highly developer specific items, as I think these really deserve there own list.  Secondly, I will be highlighting some cloud computing applications that have crept into my daily usage and replaced some of these apps. 

Not In Ninite (for those looking to get up and running as quickly as possible)

Vim, Abiword, LastPass, X-Chat, WinDirState, Freemind, Dexpot, Sysinternals Suite, Virtual Clonedrive, XML Notepad, Beyond Compare($30)

Text / Idea Editors

• Vim - “The” editor by which all others are measured, use it, love it. (download page)
• Notepad++ - Not everyone is lucky enough to know how to use Vim, also, you might have a guest using your computer or something, just in case. (in ninite package)
• Evernote - A complete noting platform, that works on nearly everything you own, must have once you get used to it. (in ninite package)
• Freemind - Mind mapping software, great for taking notes. (download here)
• XML Notepad - Microsoft XML Notepad is a good little XML Editor. (download here) 

Email Clients

• Thunderbird - Still my primary email client, simple, clean, works well with imap and Gmail. (in ninite package)

Virus / Malware Protection

• Microsoft Essentials - A shockingly well put together product, what more can I say, it rocks. (in ninite package)

Web Browsers

• Firefox - Still my primary browser, but has less momentum than Chrome. (in ninite package)
• Chrome - The young upstart, gaining in popularity. (in ninite package)

Office Products

• Google Docs - My preferred way to work with documents is now docs.google.com, but since the rest of the world doesn’t agree yet, we sill have the below options. (online only)
• Abiword - A lightweight, full featured editor that has full support for lots of text document formats… with a collaborative editing feature built in via Abicollab.  Doesn’t feel as slick as a Google Docs for collaboration, but close. (download here)
• Open Office - Rapidly closing the gap with Microsoft Office, already good enough for most users. (in ninite package)
• Sumatra PDF - Replacing Foxit on my list due to its small size, lack of nags, and / based searching.  (in ninite package)

Compression

• 7-Zip - Great open-source compression utility, supports gobs of compressed file types. (in ninite package)

Password Management

• Lastpass - Amazing, secure, end to end encypted, cross-platform with plugins most browsers and most platforms.  Where I personally keep my information. (download it)
• KeePass - While I prefer LastPass for personal passwords, KeePass is often the best solution for shared / work environments.  (in ninite package)

Messaging

• Skype - Video-conference and VOIP, great software. (in ninite package)
• Pidgin - IM client that supports dozens of networks, AIM, ICQ, MSN, etc.  (in ninite package) | Alternative: Meebo.com - I warned you that cloud options might be on here.  
• X-Chat - Great open-source IRC client.  If you need a high degree of mobility and/or use many computers. (download it) | Alternative: Use Pidgin to get access to IRC, could look at IRCCloud, but coming out of beta, the pricing structure doesn’t work for me. 

Imaging / Vector / Photography

• Picasa - Picasa acts as both a local image viewer / organizer and a tool for getting your images online, with 10x the space online as Flickr. (in ninite package)
• Paint.NET - Minimalist free image editor. (in ninite package)
• Inkscape - Sometimes you need to work with vector, and need a vector editor. (in ninite package)

Windows Improvements

• Autohotkey - More than just keybindings, automation and great features. (in ninite package)
• Launchy - Launchy is a free cross-platform utility designed to help you forget about your start menu, the icons on your desktop, and even your file manager. Read about integrating Launchy and Everything. (in ninite package)
• Dexpot - Just a year ago, this multiple desktop manager was virtual useless due to bugs… now, it is rock solid and a must have for me.  Amazing features! (download here)
• Teracopy - Improve file-copy performance and stability. (in ninite package)
• Everything - Amazing search engine for windows. Read about integrating Launchy and Everything (in ninite package)

General Utilities

• WinDirStat - Find where all that space on your drive went. (download here)
• TrueCrypt - Free open-source disk encryption software for Windows 7/Vista/XP, Mac OS X, and Linux. (in ninite package)
• Defraggler - Great little defragger. (in ninite package)
• CCCleaner - Keep the crud to a minimum. (in ninite package)
• Sysinternals Suite - Tons of fantastic utilities right from Microsoft. (download here)

Video

• VLC - Amazing Multimedia player, supports lot of formats. (in ninite package)

Audio

• Grooveshark.com - This is where I listen to 90% of my music, it has Pandora basically built in (pick a song you like, then hit Radio to hear more like it)… and now HTML and not flash, bonus points. 
• Foobar2000 - Best local media player, not that I play much local media anymore. (in ninite package)
• Audacity - Sound editor. (in ninite package)

CD Burning / ISO Mounting

• ImgBurn - ImgBurn is a lightweight CD / DVD / HD DVD / Blu-ray burning application that everyone should have in their toolkit! (in ninite package)
• Virtual Clonedrive - Great virtual drive for mounting ISO’s and such. (download here)

Internet Misc

• Putty - The most popular SSH client for window; for a reason! (in ninite package)
• WinSCP - SFTP/SCP Client, just works. (in ninite package)
• TeamViewer - Quick becoming the defacto standard for remote management, replacing VNC (in ninite package)
• Steam - Best way to buy and install games on windows, think of it as an appstore for games. (in ninite package)
• Dropbox - Software that syncs your files online and across your computers. (in ninite package)
• uTorrent - Tiny, awesome bittorrent client. (in ninite package)

Commercial Applications

• Beyond Compare - The best diff tool for directories and files on windows, absolutely top notch, the only piece of commercial software I recommend on this list. (download here)

Anything I am missing, leave a comment.