I cry at the drop of a hat these days.

First, the ones others have mentioned:

• Clannad – but only the first season
• Gurren Lagann – but not the dramatic moment in the first season that’s supposed to have that impact
• Kiki’s Delivery Service – everyone is so nice (╥﹏╥)
• Trigun (original) – Hallelujah

As for my own:

• Haibane Renmei – everyone is so nice ( ˃̣̣̥⌓˂̣̣̥)
• WorldEnd (AKA SukaSuka AKA What Are You Doing at the End of the World? Are You Busy? Will You Save Us?) – a tragic romance but it still got to me as it was meant to
• Cowboy Bebop – the ending of Ed & Faye’s stories always get me bawling
• Millennium Actress – just destroys me more than any other of Kon’s works
• The Light of a Firefly Forest

EDIT: I was trying to ignore movies but how could I forget to mention Koe No Katachi (AKA A Slient Voice)? I watch that one every year or two when I need a good cry to kinda reset.