The first 'blog' I ever came across was probably Phil Greenspun's Travels with Samantha. I suppose it wasn't exactly a blog, as Phil didn't post it on a web page originally. He posted it to rec.travel, if I remember correctly. He also posted each chapter as he travelled, around the USA. Of course, there wasn't quite the bandwidth then as there is now, so pictures had to wait awhile. This was the early 1990s. There were few webservers then. In fact I remember certain webservers posting the hours they would be up. Phil continued his travels and his writing, which morphed into photo.net and a web consulting business.
There were a lot of online diaries before 'blogging' became a popular term. It was only around the turn of the century, when I heard about blogging. We had some folks at work that thought it might be a useful thing for people to do, as to document what they were working on. The first presentation on blogging I went to was a presentation at www2002 by Robert Scoble. At this point there was a sizable community that was blogging, and Scoble mentioned that blogging was a great way to get eyewitness accounts of events. He also demonstrated some early blogging 'software', or more likely templates at that stage. I remember him showing how it was a good thing to have a calendar pointing at your archives.
At this point, I didn't do much in the way of blogging. I put a few pictures of some trips up on my old website. They're still there but not in any sort of order. Just a bunch of holiday snapshots with a few captions. It was more about the pictures than about the writing. Most of my stuff was up on the web for friends to have a look at anyways. In fact, most of the stuff I've got up on the web is still that way.
Then I got married and moved here to Switzerland. I found I was often writing more or less the same email to people when I would email them. Often I'd forget to write a few interesting things in the next email. So that, and my old grad-school roommate sent me an invitation to yahoo360's beta, which had blogging as a part of it. So I figured I'd try out a bit of blogging there. It was an interesting thing to try, but I just couldn't deal with writing stuff in the little textarea input box. So, eventually I stopped doing much blogging there. Then I got a new iMac a few months ago, and that came with iWeb, which is pretty cool, but I couldn't use it when I was on another computer, so that wasn't going to work. Now I've ended up using this blogger.com thing, but mostly because readers can see the entire entry in an rss reader, which is pretty cool. Anyways, so that's enough ABOUT blogging.