Rygar (NES, 1987)Loved this game as a kid, and I still think it's pretty cool as an adult. It's not a difficult game, but at the time I spent months pouring over it's nooks and crannies before I finally figured out how to beat it. Then I played it a bunch more, just because. I remember discovering a lot of fun bugs too, like finding places were you could go out of bounds and enter strange minus realms.
Rocket Knight Adventures (GEN, 1993)This was another side-scrolling platformer that I loved and played repeatedly. I got my Genesis out and replayed it about a month ago, and it still holds up great.
Sam & Max Hit the Road (PC, 1993)I got a CD-ROM drive and Soundblaster 16 for my Packard Bell 486 PC for Christmas 1994, and discovered a trailer for this game on a 1000-in-1 CD-ROM that my parents got me. It blew my mind, I thought it was the most hilarious thing I'd ever seen. I picked it up at the local mall in a PC game store (I can't even believe that such a thing existed, here the year 2017
) along with Day of the Tentacle because I was a big Maniac Mansion fan, and I enjoyed both games immensely but I really loved Sam & Max. I wasn't familiar with the Steve Purcell comics at the time, but I have sense read them, and watched the Fox SatAM cartoon (it's actually surprisingly faithful to the material), and played the Telltale series. The original game remains god-tier.
Final Fantasy VII (PSX, 1997)Is this the game that turned me into a JRPG weeaboo? Maybe. I loved Dragon Warrior and Final Fantasy on the NES, but for most of the early-mid 90's, I was only gaming on the PC, so I missed all the big SNES JRPGs. One of the local gaming stores had a LAN area where you went to play original-ass Team Fortress for Quake, and they had some PSOnes and N64s for Goldeneye or Tekken or whatever, and they also had a copy of FF7 for some reason and I played it and I was like "holy shit, I need a Playstation right now". I played like 20-30 other RPGs for the PSOne, and basically every one I was just chasing the rush of that first taste of FF7. Maybe I still am.
Silent Hill 2 (PS2, 2001)I'm a pussy when it comes to horror games, so a horror game has to be extremely compelling for me to beat it. I beat Silent Hill 1 & 2 and loved every minute. Silent Hill 1 was pretty janky, but I could forgive it's flaws because it was so good in other ways. Silent Hill 2 was just better in every way. I was totally locked in on this game for about a week. I would play it for a little bit, get scared and turn it off. Turn it back on about 30 minutes later.
Super Smash Bros. Melee (GC, 2001)Best multiplayer game ever. "You guys wanna come up and play Smash?", said everyone, all the time.
Half-Life 2 (PC, 2004)Just the best single-player FPS experience ever, and if HL3 never comes out, I ain't even mad. If we can count Orange Box as a single game, it would be the best game ever. Hail Gaben.
The Binding of Isaac (PC, 2011)I don't even care for the scatological aesthetics, but I still think this game is wonderful. Peak indie.
Skyrim (PC, 2011)This is really more of just a blanket pick of all of Bethesda's first-person RPGs, but Skyrim is probably my favorite. It's a tough pick, though. Oblivion has extremely robust mod support which makes it fun to tinker around with, I like the post-apocalyptic settings of Fallout 3 & 4, but Skyrim man, that was just the good shit right there, right there, sign me up for some more of that shit.
Persona 4 Golden (Vita, 2012)Just a good-ass JRPG.