One Piece did it three times. All three were really powerfull situations. And Naruto just once, but Naruto really overdoes the drama. If they made it just a little more subtle I would probably cry a lot more.
Well I haven't seen many anime that made me cry but I cried watching Naruto when Jiraiya died (probably because my grandfather died a couple months b4 and reminded me of it) It also destroyed me when Asuma died but Ive cried more watching movies or TV than anime
I know this one's a game but crisis core left me with weird feeling in my throat, couldn't speak for 3 hours.......anime wise Sola came close, good thing I've never watched Clannad.....
I've cried only once. It was at YYH when Kuwabara "died" at Dark Tournament and Yusuke just walked foward and there was flashes of Kuwabara and Yusuke's friendship + this song kicked in and I started crying.