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NES - I think it took me a day or so until I 'got' this basic layout with Super Mario Bros.

Genesis - I never quite got 100% used to the standard Genesis controller, thankfully most games only required using A & B and ignored C.

SNES - Took quite some time, as it added X & Y, plus the R & L bumpers. Didn't help that most games could be played with just A & B. Link to the Past might have gotten me used to it, but took way longer than most.

PlayStation - Going from SNES to PlayStation was pretty easy, save for the shapes in place of letters; some rigorous Parappa & Tekken action had me memorizing the face buttons quickly.  The newest Dual Shock took a few days to adapt to, since they moved what is effectively the 'Pause' button to an odd spot. Was kind of a funny moment for me when I went back to my DS3 and found myself fumbling for the Start button in the wrong spot again.

N64 - I'm not sure whether Goldeneye or Ocarina of Time forced me to adapt to this monstrosity, but it happened quickly once I really got into one of them.

OG Xbox - Remember the original? I refused to touch 'em. The sleeker, improved controllers were pretty easy to get used to from PlayStation, almost instantaneous, but fuck those white & black buttons forever.

Dreamcast & GameCube - Never happened. Something about these controllers never felt right to me. Dreamcast felt cheap. GameCube felt odd; like, the D-pad was too small or something, the gigantic A button surrounded by little buttons...nah, I just hated it, even more than the N64 controller. I sucked at GC games purely because I just couldn't stop thinking about how much I didn't like the controller, how the triggers felt, etc.

Wii - Seemed like an instant transition, though I never really liked the odd feeling of having my left hand free from the right with the nunchuk, if that makes any sense. The classic controller was a magical accessory for this system, instantly felt good in my hands with no learning curve. (Still don't really know what those Z nubs by the bumpers do.)