I own a lot of consoles. This list might not be my favourite for each console - in fact, quite a lot of them aren't - but I've opted for things that assume I might want to replay them a lot. I'm also assuming that I have an internet connection, so correct me if that's against the rules.
I went into this optimising 3 criteria:
- Obviously, I want the game to be really good
- Long games or endless games are better as who knows how long I'll be here for
- Games where you can replay with self-imposed restrictions, new loadouts or where the game has a high skill ceiling allow the game to feel fresh for longer
NES: Super Mario Bros 3. - It's got a lot of levels to explore, easy to apply restrictions via power ups, and a skill ceiling to improve speedrun times or something. NES was a tough one to choose, because none of the games would be ideal
SNES: Donkey Kong Country 3 - I just really like this game, and it has lots of secrets, a lot to do and cheats to make it harder.
Nintendo 64: Paper Mario - I adore this game, and thanks to the badge and levelling system it's easy to add restrictions to the battle. Can I beat the game with no HP boosts? Itemless? Can I use hammers only? Lots of options!
Gamecube: F-Zero GX - This game has tons of content, loads of racers to make it feel different, and some incredibly, incredibly tough to unlock secrets for high level play. It'd take me a really long time before I even unlock everything, and then there's still room to improve. This was a hard choice though, because I was really tempted to choose Animal Crossing instead.
Wii: Monster Hunter Tri - A variety of weapon options gives me lots of ways to replay this differently, plus theres a ton of content here too
Wii U: Super Smash Bros. for Wii U - Smash Bros. never gets old ever. This is the best one (for now)
Switch: Dragon Quest Builders - It's a fun RPG and a lego set rolled into one. Loads of options to be creative even outside of the base game.
Game Boy: Pokémon Gold/Silver - Lots of Pokémon to catch, tons of ways to replay slightly differently, and it's the biggest of the original GB Pokémon games.
Game Boy Colour: Pokémon Pinball - Not only does pinball have a nearly infinite skill ceiling, but there's a load of stuff to do here even just trying to catch all the pokemon.
Game Boy Advance: Advance Wars 2: This was a tough one to decide, but Advance Wars has lots to do, unlock and fun variations you can add to battles via your unit choices and CO abilities that mean it has lots of new ways to enjoy it.
Nintendo DS: 100 Classic Book Collection - Is this cheating? This way I get to enjoy an entirely different pastime on my desert island too, giving me more variety.
Nintendo 3DS: Fire Emblem Fates: Special Edition - Now, you might say that this is a compilation - well sir, I counter that this game is in fact one game with 2 lots of DLC included (you could buy both other campaigns from a baseline Fates Birthright or Fates Conquest copy), and thus I get to include three different 30+ hour strategy games with a whole host of character variations I get to use or easy restrictions I can add to mix things up a bit.
Pokemon Mini: Pokemon Tetris - The pokemon mini doesn't have many games, but this is both an endless puzzle game with lots of score beating potential, and another 'gotta catch em all' challenge that will take ages to complete.
Virtual Boy: Panic Bomber - Yeah....there weren't a lot of options on VB...
Master System: Bubble Bobble - It's 200 levels and has lots of ways to improve
Mega Drive: Toejam and Earl - random factor = replayability
Saturn: Guardian Heroes - Tons of rbanching stories and multiple characters offers a lot of replay value.
Dreamcast: Chu Chu Rocket - So, if I'm on this desert island for a long time, like, a really long time, I can literally create tons of my own levels on Chu Chu Rocket, wait a few years, and then come back to solve them anew! Endless original content
Also, that multiplayer is always fun, even with CPU bots.
Game Gear: Columns - I don't have a lot of Game Gear options, and this one is pretty replayable.
Playstation: Metal Gear Solid - I struggled on Playstation between this and a Final Fantasy game, but I opted for this because of the numerous ways I could add challenge for myself
Playstation 2: Tekken Tag Tournament - That's a lot of characters to master
Playstation 3: LittleBigPlanet - Potentially infinite new content hoorah (I haven't played many PS3 games either)
Playstation 4: Overwatch - As long as the servers stay up, I get to play a game that both rarely gets old for me, and also allows me the privilege of human interaction. Even if it is to tell me to get off Symmetra.
Playstation Portable: Castlevania: The Dracula X Chronicles - Hahaha, I'm cheating the rules once more. This isn't a compilation game, even though it is. I get to play Symphony of the Night and Rondo of Blood as freebies
Playstation Vita: Hatsune Miku: Project DIVA F 2nd - I never get tired of this one.
Xbox: Outrun 2 - I don't have a lot of XBox games, and this one's just a lot of fun.
Xbox 360: Akai Katana - I also don't have many 360 titles, but I do have a few bullet hells which I can use the time to get better at. This is my favourite of the ones I have.
PC Engine Duo: Puyo Puyo CD - More high difficulty, replayable puzzle fun.
3DO: Road Rash - 3DO options are limited...
Neo Geo Pocket Colour: Metal Slug 2nd Mission- NGPC is tough to choose again. This game has multiple paths at least though.
Wonderswan Colour: Sennou Millennium - I only own 3 WSC games. 1 is a Japanese RPG I can't understand and 1 is 15 minutes long, so I went with the third option.