Dates are foggy at the beginning, since I've been playing games for about as long as I could talk, lol. I still own all or parts of my earliest gaming stuff.
1994-1995ish - Played my first video on the NES, Super Mario Brothers. Continued to play NES games quite a bit, playing mainly Gauntlet, Castlevania III, Super Contra, and Clash at Demonhead until my dad moved on and took the system with him.
1994-1995ish Got a Sega Genesis. The only games I really cared for and really played were Sonic the Hedgehog 2 and Earthworm Jim. I didn't have very many games for the Genesis.
1994-1995ish - Got a Super Nintendo. I spent most of my time playing Wario's Woods, Yoshi's Island, Super Mario World, Super Mario Kart, and the Donkey Kong Country games (all 3).
1997-1998ish - Got a Sega Saturn. The only reason why I ended up with it was because apparently the Playstation had too many "mature" games on it. My mom was picky with what I played as a kid. The only games I ever had for it were Nights in Dreams and Sonic R. I didn't like the Sega Saturn.
1997 - Got a N64 and Super Mario 64. Of course, my mind was blown since I had never seen 3D graphics in a game before (yes, I got the N64 sometime before the Saturn). I spent most of my time playing Star Fox 64, Mario Party (all 3 of them), Pokemon Stadium, and Mario Kart 64.
2000 - Got a PSOne. I was so excited because, I had wanted a Playstation on the day I got the Sega Saturn instead. I ended up getting Digimon World 2 as my first game for it. The Playstation would have the biggest impact on me out of any other system I had. I found my love for RPGs thanks to randomly picking up Lunar 2 Eternal Blue Complete one day. After that, most of my Playstation library ended up RPGs, so I have a nice collection. Of course, the PS1 was also where I eventually picked up Castlevania Symphony of the Night, because I remember playing Castlevania III back in the day. The Playstation is also credited to getting me into the Castlevania series.
2001 - Got a Gamecube. I really didn't care too much for my Gamecube. I got Luigi's Mansion as my first game for it, and I didn't care for it either. The only good thing that came out of my Gamecube was Tales of Symphonia. I LOVED that game to pieces. It's the only thing I really ever used my Gamecube for. I get the original Nintendo back from my dad some time between 2001 to 2004ish.
2003 - Got a Playstation 2. I got it for my birthday that year, and picked out the game .Hack//Infection as my first game for it. The PS2 would become the system I have the most games for (with a total of 47 games) over time. I started off with not really getting anything but RPGs, except for fighting games and the Castlevania games. Then, I got Devil May Cry 3 after reading on some forums of other Castlevania fans who also loved the game. Tried DMC3, and fell in love with it. So, in the end, my PS2 library ended up with a mixed assortment of genres. The last game I got for the PS2 was actually recent, and it was Sakura Wars ~So Long My Love~.
2007-Current - I would pick up a Wii and Xbox 360 during 2007 (Wii early 2007 and Xbox 360 Christmas 2007). The Wii I never really cared for, other than Homebrew applications and the Virtual Console. The Xbox 360 was only picked up because of Tales of Vesperia and Devil May Cry 4. I would have gotten a PS3 for Devil May Cry 4 if Tales of Vesperia hadn't been on the 360, and at the time the 360 was cheaper. Between 2007 and now, I've also been collecting older games and systems. So I've picked up the Dreamcast, since I was never blessed to play it, a replacement Sega Saturn, and many Super Nintendo, Nintendo, and Sega Genesis games. I've also picked up many hand-held goodies before this period of time, but I decided not to mention them since I didn't mention any hand-helds in my timeline (Even though the Gameboy was EXTREMELY important to me).
All of the systems and games I picked up over the years I have kept, except for the Nintendo, which my mom broke (so I had to buy a replacement), and the Sega Saturn. My mom lost the Sega Saturn somewhere (or gave it away). I still had Sonic R for some reason though. All of my stuff all still works too, except for the Playstation game Klonoa that I had bought used in terrible shape. It never really worked great to begin with, but one day it just sorta died. Luckily, I have the Wii version now anyway so it doesn't matter.