I can remember the first animated gif I ever saw. 1996 I think.
A Frightened Boy - the first…well, something, that I remember. I guess it was the first extended video meme (beyond something like hamsterdance) I remember. I think it was the first time I thought about the fact that people were creating art and entertainment content specifically for the internet.
A trio of websites with fan-written rules for 2nd edition Warhammer 40,000 and associated games on them.
This is the first thing I thought of.
I also think of Canadian web comics (in the sense of comics scanned and posted on the web) like Space Moose and Bob the Angry Flower.
Oh yeah, many of us have been there.
I love this song. It’s from 1989!
“Deeper Understanding” - Kate Bush
In addition to Altavista, Lycos, Geocities, Hotmail, Yahoo search, and the Hampsterdance, there’s was Mirsky’s Worst of the Web and the Cool Site of the Day.
That was my first thought when I read the thread title! “I KISS YOU!”
Also rotten .com; Ask Jeeves, and Bianca’s Smut Shack (the first chat room I ever went to.)
There was a site that had live cams from safari parks in Africa and if you were lucky you’d see giraffes or something.
Man, you never see the change from day to day!
Ask Jeeves makes me think of the 90s. It was the first search engine I used. I didn’t realize that it was a search engine really, mainly cuz I didn’t know what the hell a search engine was. I thought Jeeves was a gimmick that you could ask him about the future, for advice, etc. and he would “answer” you.
I would type things in like “When will I get laid?” “Who will win the World Series this year?” “Should I ask ___ out?” Never got good answers.
I had forgotten about this - I watched it all the time! There was also a site with several streaming web cams from Paris that was fascinating.
I remember the absolute JOY of moving from dial-up to DSL. Suddenly all the image-heavy sites were viable options. Fifteen years later I still visit this siteregularly. When I win the lottery I plan to buy a castle in France. 
Who can forget Mr.T Ate My Balls?
The first real internet lunatic I remember coming across was Steve Lightfoot, who thinks that Stephen King murdered John Lennon. And he’s still at it.
How about Craigslist.org? It worked fine in 1995, so why change it?
The Really Big Button That Doesn’t Do Anything, which is still there (!) and hasn’t been updated in 15 years (!).
Well…how often do you have to update a button that doesn’t do anything?
Darwin Awards.
Snopes.
Anything AOL.
Alta Vista, Excite. Usenet Newsgroups. Yahoo (which I still use). Geocities and Tripod.
Brunching Shuttlecocks was my Cracked.com back then. Hell, I have been a lurker here since the late nineties. Joined officially in 1999.
IMDb has been around since the dawn, I think, and for many years I used it as the poster child for what the internet could be all about and aspire to.
I suppose Wackopedia has replaced that in most ways, but at least IMDb is moderated/curated.
I can’t think of any other “signature” pages from those earliest days. I was never too much into exploring the web just to see how much weirdness I could find, or following strange little pages the way FB is followed today. I had a largish circle of relevant pages (several of them mine) and only occasionally followed “look at this weirdo/idiot/inept fool” pages.
Hamsterdance, maybe.
Moving from Cafe Society to IMHO.
In this respect, Ask Jeeves (now Ask.com) has never changed.
Quimby – Brunching Shuttlecocks! Yes!