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This article lists the best and worst web 2.0 sites. I tried to pull away as best I could from the general consensus, and include some sites that less frequently appear in these types of lists whereever possible. Web 2.0 is a loosely defined term, so where the relationship between the site and web 2.0 was fuzzy I tried to explain my reasoning below. I know I forgot quite a few sites, but I limited myself to five, so that is inevitable. Enjoy :)
FIVE BEST OF WEB 2.0
5. TED.com
 TED is a conference held annually in Monterey (with a few satellite conferences held throughout the world). While TED isn't a standard web 2.0 site by any means, a significant amount of their content is about the future of the web (whether you want to call that web 2.0, web 3.0 or semantic web). A particularly interesting recent video you might want to check out to get your feet wet is: The next 5,000 days of the Internet by Kevin Kelley. I have personally watched all of their videos (hey, it beats TV), and would reccomend everyone with an interest in things bigger than themselves to check out.
TED.com (new talks posted every week day)
4. Allrecipes.com
 AllRecipes is not the oldest recipe site on the net, it is also not the best programmed, but it is insanely useful when you want to cook something quick and don't know where to start. They have the largest database of recipes on the web, and a great user interface for interacting with that database. One of my favorite features of the site is the ability to enter in the ingredients you have and automatically search the database for recipes of what you can make with those ingredients.
Some of my friends and relatives think I'm some sort of cooking savant because of my ability to make awesome food with whatever is lying around (thanks to AllRecipes Ingredient Search). Also useful for many people is the automatically generated Nutritional Information. Each ingredient you use is stored in a database by AllRecipes, and based upon the quantity of each ingredient you use they can calculate the total nutritional value of your dish.
AllRecipes.com
3. Slashdot / reddit / StumbleUpon / del.ic.ious
 Some of the above sites deserve this spot more than others, however each has their own strengths and weaknesses and the sum contribution of these sites to the net deserves a spot on this list. It is best to maintain of number of social news sites to stay on top of new content, as there are some topics that just will not become popular on a few sites for various reasons.
Slashdot Reddit StumbleUpon del.ic.ious
2. Gmail
 Gmail completely dominates the free email account market. Sure Microsoft, Yahoo, and others try to offer similar services none can come close to the depth, and wealth of features offered by Gmail. If you've never used Gmail before, it can take a bit of time to get used to, but the dividends of doing so will continue to pay off for years to come.
There are far too many great features included that it is impossible to include them all, but some include the enormous amount of space alloted to each user, the built-in instant messaging system inside of your contacts(which in itself is incredibly useful), perhaps the best spam filter out there, dozens of add-ons, and ofcourse the ability to use Google's ultra-fast search function to (very) quickly search through all the messages you've ever received. I particularly like the ability to send and receive messages from my own domain name through gmail.
If you are still using some other service for a free email account, give Gmail a solid week of use and you'll be hooked.
Gmail.com
1. Digg
 So, why are #1 and #3 social bookmarking/news sites? Well, the way I see it the web has always been about information- whether it be articles, news, video, or pictures, the idea of these sites is to sort through all the crap on the net (and there is plenty) to bring you only the best and most relevant. The question of how this can be accomplished has been around since the Internet was in its infancy, Google actually owes much of its success to helping to solve this very problem. However the ability to find what you're searching for and finding something you actually like can be two completely different things. A computer algorithm can be great at finding search strings, and matching what you're looking for, but this can only take you so far.
The concept of the actual visitors of a site ranking how whether or not they 'digg' it can be extremely powerful. Imagine the Digg algorithm being merged with the Google algorithm for search results, where the top web sites returned for given keywords must undergo the scrutiny of those visitors, and if they like the site, that site will be more likely to appear near the top of the rankings. After all, Google is in the business of bringing the highest quality content possible to its users, and incorporating an idea like this would seem like a no-brainer. (Actually its not very far fetched, though talks of buying digg have subsided for now ) One thing is clear, the web of the future will heavily depend upon the input of users, and Digg is currently leading the way. The only question left is just how far this concept can be taken, and how many different applications it will have in the years to come.
Digg has done the best job of implementing the concept of user-driven content, and is leading the pack for that very reason. Sure digg has its problems, and while most of its users are overall quite intelligent and technology savvy, some can be a bit childish (4chan?) and fan-boyish (Apple/Obama/Paul), once you get over that digg is an invaluable resource for new and interesting content on the web, and anyone who considers themselves web savvy should have it bookmarked.
Digg.com
FIVE WORST OF WEB 2.0
5. Pownce
 Pownce probably does not deserve to be singled out, because by itself it isn't all that bad. But it fails in two key departments: First, it was way over hyped and ultimately Pownce was not able to live up to that hype. Second, it is not original, Pownce is a near exact copy of other micro-blogging sites with the added ability to do the same with files (which I've always found email has worked well for anyway). Lastly, much of the publicity surrounding Pownce was attributed to their lead programmer being a cute girl, which can be a real rarity in Computer Science circles - this is great, but is no reflection of actual quality of the site.
4. Classmates.com
 When you think of web 2.0, classmates.com certainly isn't the first thing to come to mind. But that doesn't stop them from trying to invade your privacy on those real web 2.0 sites you visit. Their site does contain a bit of AJAX, so I suppose that qualifies them as 2.0. Why they suck? As I already mentioned, they advertise... a lot. Enough so that everyone who reads this article, knows exactly what I'm referring to. (which is why I recommend installing Ad Block Plus, if you're using Firefox).
3. Microsoft (Silverlight)

Microsoft in general deserves this place for its relentless pursuit of profits often to the detriment of its core users. Silverlight in particular is what gives Microsoft the #3 spot. Microsoft tends to enjoy having a monopoly over everything related to computers in any way. What especially aggravates them is when someone has a monopoly on a web service whose name is not Microsoft. I am referring to Macromedia/Abobe Flash, which has, for over a decade had the market for dynamic Internet content all but cornered. Inevitably Microsoft comes along, copies Flash almost exactly, gives their version a cool name, and hype the living crap out of it only to have the web at large not take any notice. So as fewer and fewer developers adopted Silverlight, Microsoft decided to corner the market for Internet content by taking advantage of the biggest sporting event of known to mankind, The Olympics. Who knows how much they paid out of pocket for exclusive rights to Olympic content, but it ended up forcing anyone searching for Olympic videos to download the Silverlight plug-in, and resulting in an exponentially larger user base for Microsoft and millions of annoyed web users. For this reason, Microsoft's entry into the worst of web 2.0 is solidified.
2. MySpace
 I cringe everytime I hear the words 'My Space'. There are too many reasons why MySpace deserves to be on this list. I'll start with the technological reasons, the site is designed in a completely disorganized way (particulary when compared with Facebook).
Next, MySpace was bought by Rupert Murdoch's News Corporation (Owner of FoxNews), and that is enough reason in itself to never use MySpace ever. (this isn't a political site, so I won't go any further as to why). Last, once Facebook became popular, MySpace began copying everything Facebook introduced (or atleast trying to do so) and in web 2.0 if you aren't being original especially when you have as much influence as MySpace earns you a spot as one of the worst web 2.0 sites on the net.
It was extremely difficult to not rank MySpace #1, however its popularity seems to be waning which gives me hope for the future of humanity, and perhaps this problem isn't as big as it has been in the past thanks to Facebook. Myspace annoys me so much I cannot continue talking about it, on to #1...
1. AOL
 AOL has been making (mostly failed) attempts at staying modern since AOL v2.0. Every time they do, it is: 1. always half assed, 2. not very useful, 3. a copy of something someone else has already done.
Worst of all their primary objective is quite clearly to get money out of you, whether that is by making you sign up with AOL (god help you), or by the gazillions of ads they place on absolutely everything they do. AOL has been at the bottom of many of these lists for years, and they should be proud, they've certainly deserved it.
( Sorry, I didn't link to the worst five sites, I actually care about my visitors )
Extras: I decided to include these sites because they are incredibly useful, here's why...
RetailMeNot
 Retail Me Not is a quick and simple way to save money just about every time you shop online. It isn't some program you have to sign up for, and doesn't take any additional time. When ordering something online you are often asked to enter a promotional code. Companies do this so that they can offer different discounts to different groups of people. This was a great system before everyone else also decided to bargain shop on the web, and now more and more people are taking advantage of these special offers. The idea behind RetailMeNot is to find the best coupon codes available, and probide them to you as you are checking out.
This works by having users enter a coupon code, and subsequent users try them out. If they work the users can report it, and the code can be ranked based upon this info. Rankings are based upon the percentage of time a code works for users, as well as an aging function (so successful old codes don't continually appear near the top). Ihe result: upon entering the store where you are shopping you are presented with the coupon codes that are the most likely to save you money... and more often than not, it works.
RetailMeNot.com (the firefox extension)
BugMeNot
 BugMeNot works almost identically to RetailMeNot, except it is for username/password combinations. Everyone at some time has come across a web page which required them to register in order to continue, BugMeNot allows users to use recently user submitted username & password combinations to log in directly without having to waste your time or share for private information. It works using the same voting scheme described for RetailMeNot, sometimes even works for pay sites (which technically you aren't supposed to do).
BugMeNot.com (the firefox extension)
Honorable mentions: I would have loved to include these sites, but most people already know plenty about them and I was limiting myself to five.
Wikipedia

IMDb

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Comments
Barnabas Nagy
http://mediawared.info
Jay Timmerman
http://businessof20somethings.blogspot.com/
I'm glad others think about myspace as I do!