Recommended Retro Games for Newbies?

The two GBA Summon Night games, Dragon quest 1 (any version), Klonoa, the KOTOR games (if you want a RPG), Silent Hill 1, FF VII (I recommend using a guide if you want to get all the weapons or objects) , Castlevania Symphony of the night (plus the GBA ones) and Boktai
While most of this list is good stuff, i'm gonna have to disagree with you on "any version" of dragon quest 1, if your gonna play dq1, play the snes version or later, the nes version is rather notorious for the amount of grinding required to do anything.
 
(NES) Kirby's Adventure
(NES) Contra (it's a hard game but it's fun, even if you don't get too far)
(SNES) Mega Man X
(N64) Pilotwings 64
(PS1) Pac-Man World
(GB) Pokemon Gold (or Silver or Crystal)

I think those games showcase each console's capabilities pretty well, and are easy to pick and play.
 
I always recommend the same ones, with the addition of lesser-known or popular titles:

  • Disney's Hercules, Resident Evil 2, Final Fantasy VII and IX, Pepsiman and Donald Duck - Quack Attack for PS1 (there is also the PS2, Dreamcast and PC version, but I honestly preferred the PS1 version);
  • Medal of Honor Frontline, Crash Nitro Kart, Final Fantasy X, Shrek 2 and Spider-Man 3 (yes, I like tie-ins, I'm weird xD) for PS2;
  • Civilization III, Black & White, Age of Mythology and Caesar III for PC.

It depends on how much time you can dedicate to video games, but trust me, they are real gems.
Even Pepsiman::lol::lol
Disney Hercules is an amazing game
 
Dead connection is a fun arcade shoot'em up that has detectives fighting against gangsters. It also leans into noir, so if that sounds appealing to you I would recommend it.
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