The discussion on how to run/play the games on modern systems is an easy one to solve but can include methods not allowed to be discussed on Giant Bomb's forums.
How to choose the games that you play is more subjective and interesting. I've been in the same predicament as you and I still haven't covered all of my flaws yet. Keep in mind that most of the lists you find are completely blinded by nostalgia. You need to look at why a game is good and not just what people thought about it at the time.
One strategy you may find helpful is jumping from genre to genre (or franchise to franchise), finding gameplay that you like. I found out I liked games that mix exploration and combat so games like Metroid Fusion and Cave Story are great for me.
The trifecta of SNES RPGs is Chrono Trigger, FF 6, and Earthbound. Of those, I've played Earthbound and Chrono Trigger. CT seems alright but Earthbound really grabbed me with its unique style. The cart is very expensive though. I don't think it's worth the ~$150 asking price, but that's just me.
Sonic love, as you may know from the bombcast, is 99% nostalgia. Sonic was never great and most people just didn't realize it at the time. You can play Sonic the Hedgehog 2 or Sonic 3. (Sonic 1 is especially bad, Sonic CD is ... different and I didn't like it either. Note that S1 and SCD were made by JAPAN SEGA and S2 and S3 were made by AMERICAN SEGA so they are different.)
Super Mario World is either the best or second-best 2D Mario game, depending on who you ask. Either way, it is a must-play for anyone who loves video games. You can play Super Mario 64, but it's not mandatory like World is.
Zelda Link to the Past and Ocarina of Time are great, but OoT's graphix are better on the 3DS. It's absolutely a better game for that reason and a few other technical issues that the original had. Again, nostalgia and not knowing any better means we overlooked some flaws while these experiences were fresh.
Beware of games that were difficult simply because that's how games were designed back then. Old Castlevanias and Zeldas may have been fun back then but are probably better served by their more recent counterparts (Symphony of the Night and Link to the Past).
Donkey Kong Country sucks. Its graphics suck and its gameplay isn't great either. In fact, everything Rare has ever made for a Nintendo platform has been superseded in gameplay by something else. Yes, even Goldeneye (say hello to TimeSplitters 2 for a re-imagining of that style of game that's slightly more modern).
I found Metal Gear Solid 1 (PS1) to be worthwhile even when I played it for the first time back in 2007. However apparently newer games like Mark of the Ninja and Dishonored handle stealth "better." If you want to get "into" the MGS series, you won't ever want to go back to MGS1 after playing the sequels, so you should start here if anywhere.
Crash Bandicoot and Spyro come from prestigious developers, but I played them when I was very young. People talk about Nintendo games being classics far more than Sony games...
Mostly it's trying stuff for yourself. Jeff's been going on an Amiga vision quest and not having much luck. Problem is that fond Amiga memories are caked in nostalgia just like everything else.
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