A few general comments about the music headcanons
Imagine Humphrey passionately rapping Slim Shady. I can't. I fucking can't. Dexter is in the crowd supporting him and so is Meeshell but everyone else is in disbelief.
One time, late at night, Ramona comes inside the dance room searching for Justine and finds Duchess dancing and kind of screaming to Rabbit Hole's "Violet" in a fit of feral rage and she goes out of there thinking "ok, ok, I get why she and Sparrow are kind of a thing."
Faybelle daydreams about her grand entrance as the Dark Fairy being set to Britney Spark's "Break the ice". Briar would be 100% for it were it not for the fact she wants to rebel.
With that said, Fay also once made an entire choreography among her six faithful fairies set to this mashup of Hollaback girl & Barbie tingz and she is extremely proud of it.
The entire Pink Squad sings to Katy Fairy's "Last Friday Night" on road trips and while cooking. One day they shoot a fan music video that is just the real life music video but with Ginger as Katy, Briar as Rebeca, Hopper as the nerdy guy (yes, Ginger is living the dream, and so is Briar. Hopper...not so much), Cupid as the jock, and Cupid's uncle Dionysus as Kenny G playing his saxophone solo.
Dexter & Raven went to a Taylor Quick concert together and it was the place they had their first kiss. While listening to "Enchanted".
Marina & the Diamond Cards is native to Wonderland and distantly related to Lizzie, who sees her as a fashion icon. When Duchess found out she basically begged her to take her to meet her.
Yes, Goldie Lockes, Blondie’s mom, did somehow manage to become the new wave sensation Goldie. I would like to believe this happened after her story was finished.
Little Red Sheeran is distantly related to Cerise (& Ramona) and Sparrow but none of them like acknowledging that because these are emo-punk-rock kids who obviously don’t want to be associated with a pop guy (especially Sparrow). Also, yes, he wears a little red hood.