I don't really regret buying any, although out of all the consoles I ever owned, the N64 was definitely the one I played the least. However I didn't buy it, it was a gift.
Best: The dualshock ps1/ps2 controller is my favorite, it's well built, comfortable, and the button layout is great. Also, I like the feel and design of the Genesis 6-button controller.
Worst: N64, I hated the design...the buttons were so oddly placed and it looked ridiculous.
I recommend getting the ps2. There are just so many excellent games for it, it's well worth investing in the console. Plus, many of the games you can find cheap these days.
I much prefer the DKC trilogy. I had DK64 and I didn't really care for it. But I especially loved the first two DKC games, the original was just fantastic and Diddy's Kong Quest was really challenging.
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