Anything before GTA3 is going to be radically different from the later games in the series. If you want to see how the series has grown and changed over the years then I suggest you start with wither 3 or Vice City. Or fuck it, start with arguably the best game in the series, San Andreas.
I really, really liked 3. Vice is probably my favorite for story. But San Andreas was the most packed full of stuff. GTAIV they really came into their own for storytelling. My favorite is still for GTA Vice City, silly but not over the top, has Ray Liotta's voice, and a lot of great missions with references to the 80's.
If your going to play 3 and Vice City on PC, then I would start with 3 and go forward. I find that the controls of those two games on console are terrible by today's standards and almost unplayable. If your going to be playing just on consoles I'd start with San Andreas, then move onto the hd generation.
Vice City was the only one I played much of and it was awesome. Never got into the others but I could play that one and drive around all day, looking for jumps, picking up hookers, looking for more jumps then wrecking with hookers in the car. Good times...
Whatever you do, take your time with San Andreas. Quite arguably the best game EVER in my opinion. Really have fun with it; you'd be very surprised to learn just how much is in that game, past the surface even. All of the Easter eggs, and just how far the Easter eggs go. It's quite an amazing game!
San Andreas, don't know if it holds up but I suggest playing that one to get an idea how the old ones play then jump to this gen because they are quite different experiences.
It entirely depends on you. If you can get past the dated graphics you can start with 3 and move forward. Otherwise you might just wanna play GTA IV and move on to V. Gotta admit that 3 has a lot of nostalgic value for me. Just check some gameplay videos and decide duder.
I almost feel like starting with 4 would make a better leaping point into 5. While the other GTAs are good, they are better off played on the side because the jump from last gen to next gen is such a big leap that they both have different experiences.
I've loved every GTA game, maybe with the exception of IV, and I imagine that's only because it was the only one I didn't play when it was released. Those games age terribly. Start with five.
Vice City then San Andreas, then GTA 4 and GTA5. You could probably throw in GTA3 somewhere on that list, but it's kinda hard to go back to these days, and GTA 1 and 2 are un-fucking-playable these days.
It's not like the story is connected or anything (besides a few minor character references every now and then) so you aren't missing much at all story-wise. Going back to the older games at this point is really only important if you want to see where the series came from and evolved.
Honestly, you could probably just watch this and be set.
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