Childhood - Michael Jackson
This song isn't so much about type 4 in general but is written by a type 4 about the lost childhood he longs for.
Type 4
Four - Sleeping At Last
A song written about Enneagram type 4 by Sleeping at Last.
Over The Rainbow - Judy Garland
Judy Garland's raw emotion of her type 4 personality comes through in her rendition of the song. A more recent popular rendition by IZ offers a (perhaps type 9) contrast to the type 4 feel Judy Garland gives the song.
When Doves Cry - Prince
Prince is an SX/SP 4. Elements of the song and video tie in to both the sexual instinct and type 4 characteristics.