For PPCs, I like the following, which makes it as modern and functional as possible:

Office 98 or 2001

AppleWorks 5 or 6

iTunes 1 or 2

Classilla

Eudora (older version)

Print Shop Deluxe

Battle Chess CD-ROM

For a 68K, assuming I'm not using it for educational computing:

MacWrite II

MacDraw II

MacPaint or Kid Pix

Print Shop

Resolve or Excel 2.2

Word 5.1 (if I need extra word processing power)

FileMaker II (not Pro)

Battle Chess B&W