So I own a crap load of systems but probably not as many as other people out there.  I have made bad choices and some really good choices as to what systems to buy.  Some times I feel dumb for buy a system because it feels like I threw away my money and other times disappointed that the system didn't get as much use as I had hoped.
My first system ever was my Super Nintendo. I got it for christmas in 1992 so I didn't know but it had been out for a year already.  though the one thing that keeps running through my head was that at this point I didn't know shit about video games, and so how did my parents know to get me this thing?  Wow, either they got lucky or really looked into it.  So that came with Super Mario World which is still by far, my favorite Super Mario Game.  I got other games like Turtles in Time and Super Empire Strikes Back.  I guess the other really good game I had on there was Super Mario Kart, Which until Mario Kart DS came out, I thought was still the best Mario Kart game out there.  I don't know how the fuck anyone could really like Mario Kart 64, the idea that the computer could catch up no matter how well you drove was irritating.  I could lap people in the 50cc cup but even they gave you trouble in MK64, which really didn't feel well.  I also had the first two Donkey Kong Countrys and those were great too, pretty hard at points as I remember.  I think it is these games that would lead to some disappointment on the Nintendo 64.  The one game I used to rent all the time for some reason was Jurassic Park.  I just found it to be a great game, and it was always so funny to use a gas grenade to knock out the dinosaurs.
I also got a gameboy at some point.  I came home from school and my parents just gave it to me.  It was the weirdest thing.  It had Super Mario Land 2: the 6 Golden Coins with it and that game was great as well.  Not as complex as World but still an amazing feat on that system.  I also had Jurassic Park on this system, probably because o my experience on the SNES.  Though these games I had no clue how to finish.  I don't remember much of any other games I had.
At some point here, I got an NES at a garage sale.  It came with the original Super Mario Bros and Duck Hunt with the light gun.  It also had Xevious which was a fucking hard game.  I didn't really play it that much since my SNES was so great, but it was neat to have it there.
I didn't get an N64 until about 1998, I had gotten so much use out of my SNES that I could wait.  The only game that I really wanted on that system was GoldenEye007.  Up until that point, the 3d graphics seemed like a novelty still and didn't do much for me in terms of gameplay.  But goldenEye was the game that changed it all.  It had great graphics and the single player was just as fun to play as the multiplayer.  After that game though, there was not much else to really keep me going on that system.  Super Mario 64, I got that but was not very hooked.  So I had to wait, and had played goldeneye almost exclusively for a year until 1999 when I got a few good new games.  First up was Turok 2, that game blew me away and I got it at what then seemed like a cheap 30 bucks.  The blood and gore were amazing, the graphics were also great too.  Though the gameplay seemed a little hard considering that it had a PC fps feel to it when the N64 controller wasn't fit for that.  that's why goldeneye still seemed like a better fit.  Then I got WWF Attitude.  I had recently gotten into wrestling but I was so surprised by how late the game was with the wrestlers and their personas.  Triple was still using DX music while it was obvious that should have been changed 5 months before the game came out.  But it was all made up when WWF Wrestlemania 2000 came out.  I had NFL Quarterback Club 1998 which was an impressive game and so I traded it with a friend of my dads for Wrestlemania 2000.  A great trade because I got a lot gameplay out of that cartridge.  And it was quite up to date.  Donkey Kong 64 came out later that year and I got that and was stoked.  But while the game had its moments, it was just too silly and had too much collecting to be anything near as good as the games on the SNES.  Seriously, the retard mokey, the big one and the retard monkey with the big arms pissed me off.  And the stupid rap song, it killed what otherwise seemed like a well thought out game.  The factory level was my favorite I think.
During my time with the N64, I got a GameBoy Color.  I had given my other GameBoy to my cousin on my mom's urging which I now feel was a dick move on her part.  That shit was mine, you can't just ask someone to give something up.  How could I say no?  everyone was looking.  But a few years after that incident I got the Gameboy Color with Links Awakening.  I had not played a Legend of Zelda game except for a little time on the NES one on my cousin's system.  But this game convinced me these games were some of the greatest.  It was a great game that I didn't actually finish because I got stuck in this part where a flamethrower blocked my way. I knew that I had to get the mirror shield but I just didn't know where to go.  I got Turok 2 on the GBC too, but man, did that game suck.

So about this time I felt like the N64 was running out of life.  I knew that I had missed something by not getting a Playstation and the PS2 was going to be out sometime in 2000.  But everyone was anticipating it.  Then I saw something great.  Best Buy had been running this deal where you would get a 400 rebate on a computer or anything you wanted if you signed up for 2 years of internet service with MSN.  Now, today I still think that is great deal if it were broadband, but not having had the internet before, I didn't know how slow dialup was, but still it was an opportunity.  So I convinced my parents to take them up on that and we got a dreamcast.  My computer at home was a piece of crap with 16MB of ram.  But the dreamcast had a web browser so we were ok.  Oh man, I got Sonic Adventure and Crazy Taxi.  Those two games were amazing and Crazy Taxi was the most fun game I had played since GoldenEye.  Now the disappointing thing is that this system was killed off not too long after I got it.  But The games that were coming out were amazing.  Never had I had a system where the games seemed to just be getting better.  NFL2k1 was an amazing purchase and I got it when it came out.  Then there was Marvel Vs Capcom 2.  And Unreal tournament.  When Sega killed the Dreamcast, I couldn't understand why people weren't getting this system.  At 150 and later at 100 dollars, this game system was a steal and the arcade games, RPGS, shooters and sports games were all there.  The Sony Hype machine was too much.

So I had to relent because no new games would come out for the dreamcast.  I had to get a PS2.  I found it to be a good system and the first game I got on it was Soul Reaver 2 because I loved the first Soul Reaver on the Dreamcast.  The DVD playing capabilities made this system pretty easy to secure its spot as the top system in my collection at the time.  But there were no remarkable games I wanted until I got Metal Gear Solid.  This game was great and the graphics blew me away.  I actually traded in Smackdown Shut your Mouth for it because that game was too simple and easy.  But it was not until GTA3 was in my collection did I see the light.  After that the next GTAs were must buys upon release.  I dont have many other noteable games that I like except maybe Medal of Honor: Frontline but GTA and Soul Reaver were what I remember.
The Xbox came into my mind because of Halo.  I remember seeing previews of it on TechTV before the Xbox came out but never played it.  I got a bit of money for my birthday in 2003, so I took it upon myself to get me an xbox.  I had to wait until I gathered enough money to get Halo with it.  Although I got a deal where it came with Tony Hawk 3.  Having played Tony Hawk before, I found myself to be really good at this game, often finishing levels on one try.  With the revert and manual, I could not be stopped.  But Halo was as good as I hoped and then some.  But with no Online Multiplayer, it was sorely lagging behind my experience with Counter Strike.  That was all fixed when I got Halo 2 but the requirement of Xbox Live kinda killed it.  They use to have those two month free trials but I didn't keep it going until later in 2005, when the Xbox 360 came out and I was sure to get that and saw all of what the Xbox would do with Xbox Live, now I was convinced.  But the 360 was so hard to find, it just didn't seem like I would get one for a while.
The Gamecube was a great system and presented me with the first Nintendo system where Nintendo games were it.  I got Rogue Squadron first with it and to this day believe it was the best looking game on that generation of consoles.  But After that, there was not much.  Zelda came out and that game was beautiful as well.  I had fun with it but was disappointed at how Nintendo was treating the whole online component of games.  Demo discs were easy to come by and those kept me entertained.  Though Resident Evil 4 and Super Smash Bros Melee were standouts as well.  I think it was a good choice to get that system especially since it was cheap.