As part of their 30th Anniversary of the Mac celebration, Apple has a cool year-by-year visualization of peoples' first Macs and what they used them for. Scrubbing through the timeline, it's interesting watching Internet & Email surge into popularity in the mid-90s - followed by the decline of Desktop Publishing shortly thereafter.
I've used Macs since college - in my freshman year, one of my friends had a Mac SE II, which was an amazing machine for playing Tetris (and writing papers, of course). Later, when I transferred to SCAD, the labs also had a bunch of Quadras and various other assorted Macs in the Desktop Publishing and Computer Art departments.
I've worked on nothing but Macs at the various advertising gigs I've had since I graduated, but the first Mac that I bought for myself was a 15" G4 PowerBook in 2001. The thing had 8MB of VRAM and a 500Mhz processor, and it cost me close to $4000, but it lasted a good 6 years before it started to feel old and sluggish. It shipped with OS 9, but I remember running at least up through OS 10.4 (maybe even 10.5) on it, which is kind of impressive, looking back on it. It's still one of my favorite Macs, in terms of its design, although it had its issues (the stress cracks near the hinges, the heat, etc.).
My setup, circa 2007. MacBook Pro and G5 Tower.
Around 2003, I had a brief part-time gig at the Soho Apple Store. That was a fun gig, and the employee discount helped me get a G5 tower and one of those giant plastic-bezeled 23" Cinema Displays.
Eventually, I upgraded from my old PowerBook to one of the Intel-based (and now aluminum rather than titanium) 15" MacBook Pros.
2009 - iMac 27" and MacBook Pro
When the G5 got long in the tooth, I replaced that with a 27" iMac. This was about the time I was finally sold on the iMac as a high-end machine - by now there was no point in spending $2500 on a MacPro (tower only!) just because I considered myself a power user.
A couple of years later, I got my first (and only, so far) iPad (the 2nd-gen version), and ended up selling my MacBook Pro.
Current setup: unibody MacBook Pro with Thunderbolt Cinema Display
For a while there, I was rocking the iMac/iPad combination, and it was cool, but I missed the ability to go completely mobile and get work done. Don't misconstrue that as me validating the "iPads-are-for-content-consumption" trope - the fact is, my 9-to-5 requires me to work on desktop-only apps like Flash Professional and Photoshop. Plus, I use Aperture to manage my giant photo libraries (though I'm dabbling with Lightroom more and more lately, given the neglect Aperture has been suffering).
I've always held on to the philosophy that I should get the best computer I could afford, and that way I could extend its useful life for as long as possible, and then sell it for a pretty decent price. That's worked for me for the last 13 years and 5 Macs.
So that's my Mac history - what's yours?