Having recently played through a space rogue-like (Transcendence, its awesome btw (and free)
http://neurohack.com/transcendence/), I had the urge to rewatch Cowboy Bebop. I must say, it is utterly amazing. There are so many things in it that I can appreciate and contemplate now with an older mindset than when I first watched it nigh 10 years ago. There is just a subtle charm to how the characters play out and the whole atmosphere really captures you. I definitely recommend watching (or rewatching) it. Might do Outlaw Star too.....
Anyway, I'll just state again that most of the classics have already been watched. That is why this thread is hard to really do. It is assumed that the best animes have already been watched. With that said, I am reflecting on how this experience affects me. Are there some things that I've missed because of my age or because of my lack of insight? I may go back and rewatch some of the older animes now to see.....