Damn Mihkay - that's a seriously eclectic mix!
And Jess, what a thread! What an ask! What a challenge!
: D
You're about to discover some hot-ass music!
Ok, it's gonna be tough not to overwhelm you, so I'm going to be as brief as I can. But I'm a believer in albums, so since you've asked for them, that's what I'm gonna give you.
Temple of low men - Crowded House
Sign o' the times - Prince
Grace - Jeff Buckley
Court & Spark - Joni Mitchell (even better than Blue in my opinion)
Blue Valentines - Tom Waits
If you only listen to one, make it the Prince, since pop is your thing. The man's genius will make you create a burning effigy of Lady Gaga and dance around it playing wah-wah guitar solos.