I wouldn't be able to remember the first game I ever played, because I must have been younger than three years old. But early ones that I remember loving were Super Mario Bros. 1/2/3/World/All-Stars, Donkey Kong Classics, Sonic 1/2/Spinball, and Castle of Illusion. I sucked ass at all of them, of course. I didn't even notice the difference between All-Stars and the NES versions, despite the massive graphical update. I just knew sometimes I played them on the Super Nintendo and sometimes I played them on the "Regular Nintendo."
I couldn't get past Labyrinth Zone in Sonic 1, and I don't think I ever got past Aquatic Ruin Zone, or maybe Mystic Cave Zone, in Sonic 2. Couldn't beat level 2 in Spinball, but that game only has like four levels, so I don't feel that bad about it.
I could beat Castle of Illusion, but only on Easy Mode. For those who don't know, if you play on Easy, you only play a few levels, then you encounter the final boss, but just give her all the magical gems, and the game is over. I remember my dad getting mad at me for handing over the gems, as he didn't realize it was a cutscene. It was pretty funny.
I also remember playing a lot of Cool Spot, Shadow Dancer, and Beavis and Butt-Head, but of course could never beat them. Got pretty far in Cool Spot, though. Once I got far enough that I noticed the levels started going in reverse order. I didn't realize until many years later that that meant I was halfway through the game. I didn't realize as a kid that Beavis and Butt-Head was a thinking man's game. Took me decades to figure that one out.
The first game I actually remember getting, rather than having owned (or rather family owned) before I can remember is Sonic & Knuckles. I couldn't get past Lava Reef Zone Act 2 as Sonic, though, or Sandopolis Act 2 as Knuckles. I remember at one point I got up to Lava Reef Zone 2 and forced my dad to beat the rest of the game for me, so I could feel like I did it. Good memory. He still brings that one up. I must have only been four or maybe five years old.
I remember getting Dynamite Headdy around that time, but that game is fucking hard and I still can't beat it. And once my dad brought home a Super Game Boy, but the only game I had for it for a while was Mickey Mouse. An okay game, but it was no Castle of Illusion. I also remember renting games like ToeJam & Earl, Earthworm Jim, and other Genesis classics, but I sucked balls at video games and couldn't get anywhere in them. Actually I still can't beat ToeJam & Earl or Earthworm Jim.
Shortly after that I got a PlayStation, and though I wanted it purely for Crash Bandicoot, my dad thought Pandamonium looked cool. I like that game, but of course it's no Crash Bandicoot. Second game I got was Jumping Flash! 2, which ended up being the first game I was actually able to beat, though it took me a couple of years to actually get good enough at games in general to do it. Now I can beat it in about a half hour without even trying. Finally got Crash as my third PlayStation game, but that game is hard as hell. Took me way longer to beat that. Once I got Crash I was at the point where I could actually make my own game decisions, and started collecting way more games, so I suppose I shouldn't blogpost my experiences with all of them.