EmotiPad Lite - add smileys to your emails

[Ranger Bob]

EmotiPad Lite allows you to easily insert smileys (emoticons) into your (HTML) email messages or into online message board by simply dragging them from the EmotiPad interface. The program supports Outlook, Incredimail, Hotmail, Yahoo, as well as IE and Mozilla. The free version comes with 50 categorized emoticons, additional icons available in a Pro version.

http://www.snapfiles.com/get/emotipadlite.html

I happen to have EmotiPad Plus which is not freeware like the above version but like it very much and highly recommend the program.