First i will give one song (i suggest it must be a popular one)
then user after me just answer which singer should be singing that song.
You can add with imaginative explanation like what era should it be released or maybe add some collaboration etc
Example:
Katy Perry - Birthday
My answer:
Avril Lavigne. For "The best damned thing" album as 3rd single
and also make it more rock version with more guitar from Avril Lavigne.
Use your imagination, you can make it cool, fun, or anything you like. Or if you lazy to think creative, maybe just write a name of the artist.
After you answer, don't forget to give another song, so the member after you will answer it, and so on