Mine would be the Game boy color since it was the first handheld I owned but I do have 3 psp's The PSP 1000 and two PSP 3000's but handheld gaming in my opinion is a pointless race, companies are trying to bring console entertainment to a portable system and it's never going to be as good as sitting on a couch and having a controller its almost as annoying as the motion control bandwagon (Kinect, Wii and Sony wizard wand).