If you get Office 2003, Outlook is cooler than in Office XP and older versions. (suprnova,org and a bit torrent program are all you need to get that). Outlook Express is gay with its IE integration and AOL instant messenger starter thing that doesn't disable even when you uncheck it in options. Mozilla Thunderbird is okay, but it doesn't allow you to get your Hotmail through it. But if all you have are real email accounts with POP servers and you don't have Hotmail, then Thunderbird is cool. You can work with it more than Outlook certainly; and it's one of the few good email programs that aren't made by Microsoft. Eudora's about your only other good option that we haven't listed yet.
If you need a calendar program to go with that, check out Mozilla's add on calendar. http://www.mozilla.org/projects/calendar/download.html
The only other Windows one that I can suggest is Sylpheed Claws, but I prefer Thunderbird. http://sylpheed-claws.sourceforge.net/win32/#Binaries That's where to get the Windows binary (program), and for more info, you can go to http://sylpheed-claws.sourceforge.net/ For hotmail in Thunderbird, I don't know if this works, but it'd be worth a shot: http://2mod2.com/mohot/
You can try squirrelmail. Pure HTML email client via PHP. It is a neat piece of code. I've never used it but I know some poeple who like it... http://www.squirrelmail.org/index.php It's probably way underpowered for you if you are used to Outlook...
I didn't like Thunderbird because it wouldn't empty my mail from various accounts into one folder. I don't want to have to keep up with a bunch of different inboxes, etc. for my mail.
