Well I promise not to take it that far. At least this won't be an official day, but I ran across this looking up Voc@loid videos.
The song is of Megurine Luka, the third (fourth technically) character in the Vocaloid2 software by Yamaha, singing "Like a Virgin". The great thing about Luka is that she has English phonemes build into her database, so she can sing English songs. However, it is English based on how the Japanese pronounce English, so it still sounds pretty accurate to a Japanese girl trying to sing English.
And as a bonus here is her singing "Stairway to Heaven", which I only include because the fast part at the end is hilarious.