Best of the early days (you can't have latter days without early days):
Wammo - the first local site with truly great design aesthetics, supported by incisive writing, good analysis and fresh daily servings
Aardvark/ 7AM and its news ticker
A curmudgeon is born! Long before the blogs were griping, Bruce Simpson was watching the headlines, breaking the news and poking a good sharp stick at anyone who asked for it.
Robyn is old school, yo.
Press releases on line, unfiltered content, news as it happened, long before the Dom or the Herald got moving. Headwater of the daily torrent that is today's Scoop.
Worst of the DotCom Bubble 1.0
EVentures - what was their loan site's name? Wastn't there a snail or something in the vastly expensive marketing campaign?
Not a website, but all deserving a mention:
-The 6 hours it would take to download each new 6-meg version of Netscape
-Starts with T, ends with m