Hmm... best overall experiences
Chrono Trigger and Final Fantasy VI - These came out while I was in Middle School / High School. My friend and I would play almost every day (especially during the winter) getting to the end of these. I eventually had all of my characters at ** on CT as I am working towards now on the DS version. We also worked to get everyone up as high as we could on FF VI, our Edgar was near unbeatable with Genji Glove + Atma Sword + some other awesome sword.
FFX - The last FF game I really enjoyed playing. I loved the characters (except Khimari, but I really screwed him up on the grid sphere, if I had to do it again he would be much better), I liked the plot and the notion of a real world / fantasty dream world. And contrary to popular thoughts I really liked Blitzball! The characters grow on you, the mini-games don't really hang things up for me and are enjoyable and I really liked the game.
FFVIII - Yeah, another FF game, but this one is because I was in college at the time and my friends and I played the game together. It just made the game really fun because you had someone there at all times watching anxiously to see what happens next or to support you. However the final boss battles are what sold it. It was nearing the end of the semester and we wanted to finish before finals so we plowed through some of the game and we really weren't as prepared for the final battle like we would have liked. So it was a tough fight, took nearly 3 hours but the ending was totally worth it.
GoldenEye 007 - I had a N64, four controllers, decent TV and enough friends. That year of college was all about trying to find out people's strategies, what maps which person was better at, and who was the best player out of all of us. Needless to say I hate mines on the Temple level with my friend Dan. The solo game was okay, not nearly as fun as the multiplayer though.
Hot Shots Golf (Any of them) / Mario Golf - Sure they are sports games but they are pick up and play sports games. Totally worth it for the mini-golf mini-games in either series, something that is sorely missed in my eyes from the current gen versions.
You can see that most of my best games are games I played with others. I think it is because you get some competition, some friendship, and the enjoyment factor goes up when you have others rooting for the characters like you do.
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