Punch-Out!! (NES). I discovered it thanks to the NES Classic Mini in 2016. My God, I wish I played this one long ago. What a game. One of my favourite games ever. It's just... Perfect. I never get tired of it. It feels rewarding and fun even when you know exactly what to do at any time. Whenever I don't know what to play, I just beat it from start to finish in 20 minutes. Between the NES Classic Mini, original NES, 3DS VC, WiiU VC and NSO I have probably put more than 1000 hours in it. Most replayed game in my life, and that's saying something considering I've been replaying the 2D Metroid games every year since 2003.

Metroid and Deus Ex.

Have you tried Space Invaders Infinity Gene? I found that a lot of fun.

Deus Ex I take it your talking about the original, so did you play the later console games before it?

Yep, then I couldn't get into the original.

I imagine it's the same as when you play HL2 first then try to play Half-Life. It looks very dated.

Yes it's a genuine classic, but when talking about decades old games I'm sure  we have all had the experience where we have played for the first time or replayed these games of yesteryear only to realise that even games who through pushing either there genre or gaming in general forward has resulted in their dna underpinning many of today's games became classics they are still products of their time, especially when they are 3D polygon based games that we know don't age well mainly because they are very dependent on the tech underpinning them and also being popular the underpinning tech has risen rapidly increasing the differences between the old and the new, it just goes to  shows how much of a factor the actual moment we are doing something plays in our lives. still on the other side you also have some games that age well but were mediocre and will remain that way no matter the moment. 

Is the Trails in the Sky series a reference to you wishing you having been more aware of them before playing the coldsteel games first, or just wanting to have played them at release.

Yep, all the good mechanics which were all new back then have been copied and refined over the years by many many games. The total revolutionary feeling of half-life in story presentation and AI is now standard stuff. So when you play it after playing all the refinements, the original mechanics feel outdated. Plus a lot of the action movie tropes half-life used for inspiration and humor are now also a thing of the past. Games are as much a product of their time as tv and movies.

I can also add the 2D zeldas to this list. I tried Link's Awakening on gameboy and tried to get into link to the past on the Switch. It just doesn't click with me after 3D Zelda. I would have loved them before playing OOT, I'm sure of it.

I wish I had gotten Paper Mario: TTYD back then already since now it's just way to expensive to get.

I have some of the Trails in the Sky games on steam but I have only played a couple of hours of the first game, I have played all the Cold steel series on PS4 and it is pretty much it's own story set in a neighbouring empire with a story that follows a cast of young military cadets starting college called class 7, there are a some references to events in trails in the sky, but those are mostly entwined with what you and your classmates learn as you travel across the empire training and mostly relate to past events that occurred across the whole continent and they are usually delivered by talking to npc's and through certain events that unfold across the wider story, also all the important history, people, creatures, recipes etc are put into your notebook for you to peruse at your leisure ,while this and persona are in many aspects different games, the aspect of following a group of students and watching them grow is very persona like and from my small playtime with trails it's what differentiates it from the trails in the sky games, so I in the end I never got that I need to play those other games feeling, so my  hearty recommendation would be to purchase Coldsteel 1 and see how you like it .

Fire Emblem