UltraEdit
by IDM Computer Solutions
The Best Editor.   It's been here since 1994 with practically no alternatives; full-featured, professional, fast, cool, handy, adaptive. I can only mention the increasingly capable SublimeText as a real competitor but UltraEdit still beats it in many ways. (Not on Linux, unfortunately.)
Total Commander
by Christian Ghisler
Norton Commander, anyone?... Even better, Volkov? Whichever rings the bell, you can see how this concept has been with us from the very first days, gradually evolving on Linux too (as Midnight Commander), and it's still the most viable approach of handling things in a file system.
Everything
by David Carpenter
All your files.   Always there, instantly. You start typing some letters and you get the hits, realtime. Amazing. The kind of tool that makes you wonder why it's not already integrated in Windows itself. So natural and handy that it actually hurts to live without it once you've worked with it.
PaintShop Pro 7
by JASC Software
PhotoShop in a swiss knife.   Actually, if you can work with this one you'll never really need Adobe's heavyweight resource hog. This one is designed to help your work; it's fast, handy and knows a lot. (Version 7.04 is from 2001; in 2004, Corel bought them and turned PSP into a useless giant.)
OneNote
by Microsoft
Free sketching.   A great surprise from Microsoft, it really is. Practical and fast, stuffed with great ideas and handy little solutions, this tool is the definition of ''well-thought''. Perfect as a screenshot tool as well. Love the whole thing, I simply can't believe the Windows guys did this.
TortoiseSVN
by Stefan Küng, Lübbe Onken and others
Version Control.   No, thank you, I hate Git. Subversion is much more reliable straightforward, and Tortoise is one of the best (and most popular) clients. It has a very good merging tool, has smooth transactions and practically never gets in my way. Thank you for helping without blocking me.
KeyManager
by ATNSoft
Keys, reinvented.   It means control. It can attach actions (like keystrokes, macros, etc) to any key combinations, including exotic media control keys, or even the buttons of your mouse. Yes, that one on the side, too. You can even make dropdown menus to reach several actions. INSANE.
WebDrive
by South River Technologies
The world is a drive.   Just connect any server and use the files as they were local. WebDrive was not always fully reliable; now you can finally trust it. Operates silently in the background, can handle WebDAV, FTP, SFTP, FTPS, whatever you can think of. And it's quite configurable. Give it a try.
Toggl
by some guy I can't track down
The simplest thing when it's about tracking time. It does just that. Tracks your time. So many hours for this, so many hours for that. There's a very good desktop app for it to make it super easy to keep tracking, and there you go - just check which project stole all your time.
RescueTime
by Joe Hruska
Another time tracker, but this one is not aiming for a per-project result. It tells you how you use your own time, I mean how many hours have you wasted for messaging with girls and hanging on Facebook. The single most fruitful form of trolling yourself, and it works like magic.