CryptaGram
Two word games in one: cryptoquote and wordsearch.
Size: 7.6MB 
OS: 95/98/ME

Classic WordZap
Create the most unique words from a given set of letters.
Size: 284KB
OS: Win 9x/ME/NT/2K/XP/2K3

Gwerdy Wordy
Application designed to help players on a multitude of word based puzzle games.
Size: 1.19MB 
OS: Win 9x/ME/2000/XP

5 Star Word Engine
Build the longest possible word from a randomly selected set of letters.
Size: 1.93MB 
OS: Win 9x/ME/NT/2K/XP

Lettris
Drop blocks and spell words then drop bombs to remove unwanted letters.
Size: 2.4MB
OS: Win 95/98/ME