Tough question. Usually I'd go right to PS2, but I've been collecting a lot of PS1 games lately and starting to really warm up to that system.
But for now, I'd go...
4) PS3 - Probably the weakest of the generation, but still a nice machine with some great exclusives: Infamous, Uncharted 2, The Last of Us, and Demon's Souls, which alone is worth the price of admission.
3) PS4 - This system has two problems. The first is that "AAA" third party multiplats, the PS4's bread and butter, are in decline. The second is that Sony's first party studios have been in decline since circa 2009. The Last Guardian is great, but it arrived three years into the system's lifespan and its director is no longer on the Sony payroll. Indies and third-party exclusives like Nier, Nioh, and Spider-Man look to save the day.
2) PS1 - Sony's first-party studios were still finding their footing, but third parties more than picked up the slack. PS1 hosted some all-time great games, including Metal Gear Solid, Symphony of the Night, Street Fighter Alpha 3, Tomb Raider, and Final Fantasy VII.
1) PS2 - What makes PS2 so great is that it represents the height of Sony first-party software and, arguably, the height of third-party software. Sony scored with Ico, Shadow of the Colossus, God of War, Killzone, and Jak and Daxter. Third parties scored with Ratchet & Clank, Grand Theft Auto, Devil May Cry, and Metal Gear Solid.