Of the oldest systems I only ever played the NES. I know my uncle had an amiga somewhere, but I never tried it, and never tried anything else. Had a few game and watch games from around the same era. Cannot judge them early systems.
I could never get used to the button layout of the genesis controller. Felt like I needed to create new joints in my fingers to get the combinations needed right. Even if there are great games here I never played them much. Gunstar Heroes was fun.
The N64 had one of the strongest line ups of first party games on any system. Did not mind the strange controller layout but the control-stick made it impossible for me to revisit the games later on. I much rather play the games on later systems like the game cube release of the Zelda games. Still a contender for sure when it comes to the best runner up.
The Xbox was by me seen mostly as a joke back then. But it had awesome online capabilities, Two of my friends that got one had a heat problem and one of them actually started a small fire. A third friend installed linux or something on the thing and used it to emulate SNES games and other older systems. I had fun with Halo a couple of times, a game in a genre I never play. Sums up my whole experience with the Xbox brand. Neve got or even played any of the other Xboxes. Used the 360 controller on PC at least, great controller.
The PSP was the cool kids system for me back in the day. People without "Nerd" tattooed on their soul played it. I wanted one even if I did not really like Patapon or really any of the games a tried. But it looked so sleek.
PS3 is the system that sort of won me over to the Playstation. I had played a lot of PS1 and PS2 games before but the best titles on PS3 was on another level. in particular the Naughty Dog games. Bought my third copy of Resident Evil 4 for the system. Still liked the Wii-version better, but my ex took our Wii when we broke and i needed my RE4 fix. I sort of skipped the whole next generation and just kept on playing PS3.
PS vita... Well, it existed I am told. Never had one, never knew anyone who had one. To be fair I was not much of a fan of the 3DS either. That whole system generation almost lost me as a gamer. Was disappointed with pretty much everything.
Xbox one. No.
PS3 is my winner of best runner up.