all things considering i'd go for the ps1/2/3 controller, when it originally came out i thought the design was quite good, being about 8 the controller fit my hands well, much better than the much clunkier N64 controller which i found hard to use, and obviously better that some of the other offering of the time, and previously.
Even on the PS2 it wasn't terrible, the continued design bought a bit of familiarity, the constant layout made it easy to get to grips with having been using the controller for the last 4 years anyway, and it was still better than the majority of the competition. but on the horizon was the Xbox (or the black beast

), the initial design of the controller was perplexing, what with being so large and having an analogue stick in the wrong place (not to mention 'R1'/'L1' being 'black' and 'white' in an odd place) but this controller was quickly revised to cater for the small handed japanese (why have big hands if one of the things they're most useful for is so small after all?) the 's' version of controller was just about perfect, by then my hands were much bigger (obviously not being 8 any more, but closer to 13/14) and the fit was near perfect My thumbs, having been horridly contorted on the DS2 now found a much happier home at more muscle friendly angles and my gaming improved, no longer did i have to endure the tedious cramps induced by a 2+ hour session on the PS1/2, i could cheerfully play all day (if i could divert the call of nature and hold it in long enough).
then came the Xbox 360 controller, sticking with it's winning design it made only 1 major revision, shifting black and white to the R1/L1 positions of the DS1/2 controller, a good, sound move. Sony would have to do something to remedy their poor controller design, now only with 2 major competitors they needed something to match the winning controller designs of Microsoft and Nintendo, a drastic change was needed to win over comfortable hand lovers everywhere and so they designed the boomerang, horrible looking and still poorly laid out they realised it would not be received well, and so, sticking to the tried and true method they returned to the old ways.
however removing the one thing that made the DS2 controller good (the DS bit!!!) they proceeded put a motion sensor inside the controller, poorly implemented and absent form many games this proved to be a pointless feature and many wished to see the DS return.
and so, Sony, taking a controller 12 years old, and at least 6 years out of date managed to make a bad design worse. ignoring calls for a more ergonomic controller they simply re-did what they knew. poor ergonomics, bad size, awful blind spots, sloping triggers make it impossible to stay on the ball in heavy gaming sessions, a lack of dual shock made games more 2D, no longer feeling the effects of a grenade going off at your feet, or crashing in to a barrier at 150MPH.
and that is why sony's is the worst, knowing it's out of date. failing to re-design to any meaningful extent, ignoring pleas of fans and refusing to adapt and then to top it all off taking away what few good features it had left.
TLDR? sonys controller sucks