The 5th gen was a weird one. It was a highly transitional era, pretty mind-blowing at the time, but the vast majority of the games from back then have aged incredibly poorly. So nostalgia winds up counting for a lot more here than it does in my other lists.
Here are my favorite 25 games in ranked order, with some runner-ups listed alphabetically.
Eligibility: Released on PS1, N64, Sega Saturn or Game Boy Color. Released on PC/Arcade during 1996-1999 in the US.
Noticeably missing because I haven't played them (much): FF Tactics, Baldur's Gate, Homeworld, Metal Gear Ghost Babel, the Resident Evil games.
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On the single-player side, this revolutionized first-person shooters and set the standard for what we expect today. On the multiplayer side, Valve fostered the best damn mod community that has existed before or since. Half-Life was practically a platform unto itself. Counter-strike was the biggest hit of course (and that would probably be my real #1 if I was counting it as its own game). But a lot of other mods were great too. I loved Team Fortress Classic, Day of Defeat, Action Half-Life, Wasteland Half-Life, even the vanilla deathmatch could be fun on certain maps. It seemed like every week I'd learn about some cool new mod that I'd want to check out. Good times.
Quake 2 is probably not a great game, but I was damn near obsessed with it. It was my first introduction to online multiplayer, I'd play on a 56k modem with a ping between 100 and 400 and I loved it. Before Half-Life I was way, way into the Quake 2 mod scene, constantly checking Planet Quake to find new shit to play. Threewave CTF was mind-blowing at the time, Rocket Arena was great. There were a lot of other neat mods like Jailbreak, Catch the Chicken (yes really), Headhunters, Blast Chamber, etc, that never really got a large player base but the Internet was new to me and it was more about the joy of discovery. The single-player was not too shabby either. I loved the tone of the story, I'd watch that intro cinematic over and over again... As a moody teen it was right up my alley.
I had a crew of people that would be playing this constantly, it was amazingly fun. It seems that Melee has become the overall fan favorite, but the original always felt better to me.
I played Fallout 1 & 2 back-to-back (never finished 2), lets say they share a slot here.
The best story in video games.
Tribes was an incredibly innovative and influential multiplayer game that, sadly, has largely been forgotten today. It was the first FPS with wide open terrain and vehicles, and everyone had a fucking jetpack. The main focus was on CTF, but a big dueling culture emerged too. Nailing someone with a disc while you were both in midair was incredibly satisfying. There were lots of different options for your armor type, weapons, special equipment like mines, etc... We'd spend a ton of time experimenting with different loadouts and we didn't even have to unlock any of it! Imagine that! The 2012 F2P reboot only lasted for a few months, and the recent kickstarted spiritual successor never even broke 800 concurrent players. This style of gameplay is probably gone for good, but it was a hell of a thing to experience.
My head knows that OOT is the better game...
... but my heart belongs to Majora's Mask.