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To think back a few generations I'd say the SNES controller and also the Mega Drive controller(even worked with Amiga!). I can't choose which one I liked the most.

The generation after I'd have to say the DS controller, when they added the dual sticks it's easiest the best controller. But I also enjoyed/liked the Saturn controller.

For the sixth generation I liked the GC controller the most. The DS2 was also a nice controller.

Last gen I'm not sure, I've heard that the 360 controller is great, but have not used it as much as the other controllers. The Sixaxis is not my favourite, that's for sure. But the DS3 was really nice, and I did enjoy the Wiimotes at first but they later bored me. So for last gen I guess I would have to say the X360 controllers, even though I haven't used them too much. Or else the DS3.

The DS4 is absolutely a great controller, and perhaps(probably) my favourite for this gen. :)

So I suppose overall I'd say the DS-family of controllers, I have enjoyed pretty much all of them.