For Scruffy Dude, a lot of things by Billy Joel absolutely hit the mark. This one always strikes home:
I Don't Want To Be Alone Anymore: Billy Joel
Also, 'Goodnight My Angel', also by Billy Joel, for... reasons.
Also also, bagpipes, and Celtic-inspired music in general.
For my Elven lady, this piece by Simon and Garfunkel really resonates with me.
For Emily, Wherever I May Find Her: Simon and Garfunkel
Glitch: Probably a combination of weird electronica, combined with the most irritating 90's pop you can imagine. She's the kind of character to get roaring drunk and 'sing' 'The Vengabus' at the top of her lungs.
Blues Scale: Miles Davis and John Coltrane. Cool school jazz, basically.
Boxer: So long as he can work out to it, he isn't fussy.