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Cerebralbore101 said:

What's the most disappointing game system you've ever owned? Did you keep it? Did you trade it in? What games did you have on it?

I hate to say this but Nintendo 64. I owned one as a kid and loved it. Then I bought one to collect for six years ago. The system just has not held up well over the years. Many games on the system like Goldeneye, and Turok aren't classics. They're just old. I can't get over the N64 fog when playing games like Rogue Squadron. True classics for the system like Zelda, or Starfox were remade for another system ages ago. Collectathon platformers just kind of all feel the same. IMO it was a revolutionary system for it's time, but N64 just has not aged all that well.

I wound up trading it in eventually.

I had...

Goldeneye
Perfect Dark
Turok
Turok 2
Banjo Kazooie (The best collectathon platformer IMO)
Banjo Tooie
Conker's Bad Fur Day
Super Mario 64
DK 64
Rogue Squadron
Resident Evil 2
Ocarina of Time (20 FPS has not aged well. Get the 3DS version!)
Majora's Mask
Excitebike 64
Starfox 64
Battletanks
Battletanks 2

Did you have the N64 Expansion Pak in the system?  I remember a huge improvement in the graphical detail of Rogue Squadron after getting the Expansion Pak.

The Atari 7800 by far was my most disappointing system.  The system released around the same time as the NES, but felt like a dinosaur by comparison.  I remember having Pole Position 2, but not much else.  The following Christmas, my family bought an NES and The Legend of Zelda and never looked back.  Here's side by side comparisons of Double Dragon, Ikari Warriors, and Rampage on the Atari 7800 (left) and the NES (right):