You can´t get any cooler than the software of the 80´s. Everything today is just footnotes to a great legacy. Which however doesn´t mean I don´t enjoy reading the footnotes. There are certainly some better programs today, but back in the day DeluxePaint, Aegis Sonix and F18 Interceptor simply blew your mind.
BTW. some C64 stuff is pretty cool as well. Anyone remember "Final Cartridge III"?
I agree, nearly everything had wow factor and drew you in. But I will say I have been wowed recently too. e.g. The Sims No. 1, Medieval Total War, and Battlefield Vietnam (great theme poor gameplay).
You can't forget a few 90s classics like Myst for example.