Proof of Life (hdsjds who's the producer again orz i forgot feat. Kagamine Rin) had me crying for... I dunno. 10-30 minutes. Longer than Servant of Evil (I only cried for a few minutes lol), surprisingly.
Let us not forget the song in this beatmap. https://osu.ppy.sh/s/129676 The music box-like part makes me imagine a sad scene with a pairing and... well. Like. I can handle the song it's just... the music box part has this bittersweet feeling.
I love Rooftop Prince so much.. Such a beautiful Korean Drama.. Also.. Sad songs + animation: 15 years of pursuing a cute boy - Hatsune Miku Reboot - Hatsune Miku and Megurine Luka The Love-struck Kitty won't be Discouraged! - Megpoid Gumi Fools among the Stars ~Kappa~ - Megpoid Gumi