What vocaloid songs matches withc Homestuck character?

Im doing one of em' Youtube ipod song theme for characters. And I wanna make it vocloid related
Write a Homestuck character and any vocaaloid song that sounds perfect for the character
ex. dolch, dirk - Winge Jp Von Luka(since he is kind-off an Otaku and the song s about the world of japanese animes and stuff)
Damara - Shooting star, sterne Von Miku(The lyrics....they just...cod...)

So please just Kommentar what song serves what charcter 8D
Du can also give me other ideas for those example charcters I used if Du want