Gran Turismo 3 - I loaned my copy of Silent Hill 2 to a friend, and he loaned me GT3. Sadly, he hardly played SH2. But I got plenty out of GT3, even if I completely sucked at it.
Gran Turismo 4 - A few years later, and I find myself in posession of my very own copy of GT4. And this game completely blew me away on so many levels... the gorgeous graphics, the insane amount of content, all the great features like photo mode. My enjoyment of GT reached obsession levels with this title, and slowly through sheer determination, I start to suck less.
GTHD - Cue the next-gen consoles, and I found myself begging for a PS3... with GT no doubt being a significant factor in my choice of hardware. In the early days of PS3 ownership, there wasn't much to play except for Oblivion... and, of course, GTHD.
GT2 - During the wait for a more substantial next-gen release, I decide to start looking for copies of the older GT games. The first one I found was GT2. Didn't play it a whole lot at the time, but I did love that sweet opening video.
Tourist Trophy - While technically not a GT game, it's great nonetheless. Although due to how acquiring new bikes works in it, I found myself struggling to make significant progress. Like GT4, eventually I started to get a little better and was able to make a little progress. But after a long break from it, I found that what little skill I acquired had completely vanished and I was too discouraged to try and regain it. I guess it's not like riding a bike after all, eh?
GT5 Prologue - Finally, a (slightly) more meaty next-gen release! There's not much to say about this one, other than I was completely in love with the cockpit view, and that I now know Suzuka like the back of my hand thanks to it.
GT PSP - Two months of boot camp wasn't bad. Learning that GT5 was delayed afterwards... now that was rough. But I now had a source of income, so I decided to pick up a PSP Go and GT PSP. I didn't really love it, but I played it off and on... and still do to this day, although now I'm playing it on a Vita.
GT1 - A little later, I decided to order the very first GT on Amazon since I had yet to nab a copy of it. Didn't really play it much though... not as much as I played the demo of it on the Pizza Hut demo disc many years ago.
GT5 - Eventually the fabled GT5 came out, and... I liked it, I guess? Didn't obsess over it to nearly the same degree I did with GT4 (or even GT5P), but I appreciated the dynamic weather and time of day. I decided early that the disappointingly small A-spec wasn't worth it, so I found myself mainly just working my way through the special events... some of which were great, some of which were meh.
GT Concept 2002 Tokyo-Geneva/GT4 Prologue - A little over a year later, and I find myself stationed in Japan. And in Akihabara, I find these two selling for 400 yen each. I'd be a fool not to purchase them. I also bought a Japanese PS2, but sadly I haven't yet gotten around to trying them out yet.
GT6 - GT6 was announced and surprisingly released when it was supposed to, and it was mostly what GT5 should've been. Unfortunately, thanks to being busy with work, I haven't played this one as much as I would like. The A-spec mode is still small, but the star progression system is worlds better than the grindy leveling system of GT5. Though I do plan on getting back into it here soon while we wait on the eventual GT7.