I think Clannad takes the cake for sad anime that is now timeless for being so sad. I am so happy the VN was ported to Switch, it is so worth it!
My other favorite is Galaxy Express 999, totally a blast from the past (1978). So many episodes create a sense of dread and emptiness that is hard to describe. The show is very slow and stylized. I personally think it has aged very well considering it is 42 years old