Nothing on the PS2 was compelling enough for me to buy one at the time, and I found the dualshock's stick layout uncomfortable. Then Xbox came along with Halo and that was that, really.
The PS3 was overpriced and underwhelming while the 360 knocked it out of the park. Still my favourite console ever.
Then the Xbox One and PS4 happened... Yeah, MS ballsed up the messaging and then floundered even more every time they tried to re-explain their ideas, but I honestly think the whole put-the-disc-in-once licensing thing was ahead of its time. The people claiming that they couldn't possibly connect their console to the internet for 2 minutes every month to refresh their licences were being disingenuous, and Sony's "this is how you share games on PS4" bit, while understandable from the free marketing perspective, just came across to me as both short sighted and incredibly mean spirited.
Since then I've been team Xbox by default, but they've never really recovered from the shit show that was the Xbox One launch and it's a shame.