I'd say NHL 14 on PS3 is the best I've played. For management, Eastside Hockey Manager is a solid title.
I'd agree that 14 and Legacy are the best overall games. I haven't played a title post-PS3, but from the sound of things, a lot of people say the series peaked then and hasn't reached the same heights since. I keep trying to get into previous versions of Franchise Hockey Manager, but it hasn't grabbed me yet. I should try EHM because of its proximity to FM.
Funny enough, I have been on an 16-bit bender, playing all the Genesis NHL titles and Tecmo Bowl, and those games still hold up. NHL 94, of course, is a classic, and I remember many late nights battling with my older brother and his friends, and my mom making me go to bed.
NHL 94 is still great - it has its flaws, sure, but it is just a banger of a title. I think the more I play it, I see more varied goals from myself and the CPU (I don't do the across-the-crease cheat unless it's a realistic opportunity). NHL 95, I think, is a
touch better - improved AI, a full season mode (where you can control all of the teams!) - but the pacing of 94 is better. 96 has it all and is the most polished, but I wish I could slow down the gameplay.
97 and 98 could be so good, especially 98, where you have the option to change the game speed, but the AI is hyper-attacking, but in the worst way possible. It shoots at every opportunity from inside center ice, so it takes all these pointless wasters and never lets its offense set up, and you end up distributing all the time with your goalie. It also has the two-line pass, though there are mods that remove it, which stifles a lot of the fun.
94 is a bit like PES 6 for me - fun and easy to play, but not my all-time favorite, and it has a ton of different mods available. Pretty much every season is available on
NHL94.com as well as Olympics/Canada Cups/European leagues.
Tecmo Bowl - well, that's another thread, but god damn that game is fun.