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I love Tumblr, been using it for nearly 4 years! While I agree that self expression matters, at least for me, there has to be more than that. MySpace also allowed users to change up and remix their profile page with custom CSS/JavaScript code but they still lost users to Facebook's clean design. MySpace became a digital ghetto, made evident by the glitter graffiti-like images posted user's comments. What I like about Tumblr is not only that it allows me to customize my tumblog but that it helps me with a set of great looking templates!
What myspace did was a horrible implementation of customization and community features. It was an eyesore. They might have cleaned up some of their act now, but its too little too late.

Tumblr is more like blog+facebook+twitter, made ridiculously easy; minus the clutter and noise.

MySpace is arguably worse now than it ever was. The default profile looks much better, but that's about it. There are still obnoxious ads everywhere. They've tried to copy, poorly, a bunch of facebook features like the news feed, but it's crammed full of commercial spam. The profile management tools are clunky and annoying. Even their logo is now horrible.

But the issue wasn't that MySpace was an 'eyesore' or that Facebook was 'clean', except to the extent that MySpace was full of distracting ads. Facebook is full of stupid crap, too. Facebook made the better choice to focus on innovating community features, which was its strength, where MySpace failed to innovate along its own strengths. Maybe was poorly designed or poorly managed, or maybe they simply panicked and tried to be facebook but clearly not as effectively. I don't know. But now it's a mess.

Facebook was and is a better tool for interacting with your social network than MySpace, and continues to innovate in that space. MySpace was, at one time, better than facebook at self-expression, media sharing, and making connections with semi-random strangers. Now, I'm not sure it's really good at anything particularly interesting.

There is a quote I like, "Great people talk about ideas. Average people talk about things. Small people talk about other people."

Tumblr wins because it turns ideas into things and makes them easier to talk about. Not only this, but it also makes it really easy for your writing to get traction with others, assuming it's reasonably interesting. It's like training wheels for future intellectuals, a perfect match for intellectually curious kids in their late teens and early twenties. (In fact, it almost invents a new category of online interaction that I'd call 'intellectual sociability'.)

This was my analysis of Tumblr a year ago, and I think it still holds perfectly today: http://news.ycombinator.com/item?id=961523

I run a site with fairly high traction with teenagers specifically teenages from california and tumblr is very popular with that demographic. From the outside looking in, they seem as excited about it as I was about friendster circa 2003, like this blogging thing was just invented. My take on the success of tumbler, for this demo at least is that it successfully implements standard blog tools that were once too nerdy for the masses (rss subscriptions, auto posting to twitter / fb, making it easy to post any type of media, making it easy to theme their blogs). In fact most of them use it like a twitter on steroids, posting pics and videos and viewing them without having to click on a like to a seperate service.