While it’s true we see a ton of innovation on the internet (it’s what drives it to begin with) there’s been some stuff that was just nothing but a miserable failure from the word go.
Here’s 5 of them. Some are old, some current.
WebRing
The concept: To "join" web sites together in a circular structure (the "ring")
The reality: A bunch of crappy web sites that don’t relate to each other at all desperately trying to whore each other out for the sole purpose of generating web traffic.
WebRing actually still exists and it still sucks. Granted, this was one of the first attempts to connect web sites with common interests, but it ended up being nothing but a big ball of fail.
Tag cloud
A tag cloud is a "weighted list" of a jumble of words where visually bigger words are discussed more while smaller words are discussed less. See examples here.
The concept: Visually bigger words (like bike instead of bike) mean people are talking about that particular whatever-it-is more often.
The reality: These words when clicked lead to articles/sites/pages that usually have nothing to do with that word whatsoever – OR – the words presented are so unbelievably generic that it never leads to any useful you were looking for.
The tag cloud is one of those Web 2.0 things that just doesn’t work. It doesn’t matter if you have it enabled on your personal blog or use a big-site way of doing it because tag clouds suck.
LinkExchange
This, much like WebRing, was a failed attempt at connecting web sites with similar interests by putting "badges" somewhere in your web page/site. The only difference is that it was more corporate and required cash.
It didn’t work.
Microsoft bought this, realized it sucked and changed it to be part of Microsoft Office Live. In its current form it has absolutely zero resemblance (thank God) to the old LinkExchange.
Badges
The original "internet button" was a 88×31 graphic.
Remember these? 
In the Web 2.0 version this was made smaller into an 80×15 "badge".
Badges look like this: 
For whatever reason someone thought it was good that with ever-increasing resolutions on computer monitors to make graphics smaller and harder to read.
Stupid? Yes.
"Splash" pages
This is more of a web usability thing than anything else but it bears mentioning because it still happens today.
"Splash" pages, a.k.a. the "skipintro", is some dopey Flash-based "introduction" to a web site. This has been widely panned on web pages like Web Pages That Suck because it serves absolutely no purpose other than to annoy people. It’s not "cool" or "hip" or anything like that whatsoever.
If you have your own web site, I have three words of advice for you concerning the intro page: Don’t do it.
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