I always liked how simple the school computers running OS9 were in comparison to our home Win98 computer. I would say that ClarisWorks is what really drove home the point that Macs are easy to use, because everything in that program seemed so logical. The Paint program was especially good! HyperStudio was another example of a really, really easy-to-use program that could produce great results. Always wished my Windows PC at home could do the same things so easily.
What made me REALLY want a Mac was the first time I saw an iPod (the original 5GB), the iMac G4, and my school's white iBook G3's. I remember wondering how the hell our laptops were getting internet when there was no wires connected! Ads are no substitute for holding one in your hand! I always thought the "Switch" ads were too self-consciously whimsical and annoying with that tinkly background music.