It's too hard to pick my top five. It changes too often. Right now I'm thinking:
The Bruisers- One Law for Them...
The Sun Records Collection- and if I'm not allowed a box set, I'll take disc one
The Smiths-Louder Than Bombs or maybe that greatest hits one
Cocteau Twins-Four Calender Cafe
Ella Fitzgerald- Compact Jazz
I'm glad I'll never have to make this decission IRL. Too tough. Ms. Mom- I love reading in your posts about your musical tastes! I don't think I would have survived my teen yrs w/out the Smiths, the Cure, etc. I was so seriously IN LOVE with Morrissey back in the days of black and white striped tights, black old lady dresses, black hair, black lipstick, black... well, you get the picture. I remember thinking "I wear black on the outside because black is how I feel on the inside" was such a clever and witty line. I still love the music, have really gotten into it again recently, although I'm very glad that my tastes have become a lot more inclusive.

Maybe we should start a "If you were Gothic" thread...
Etoile, CanOBeans- I love hearing about other people who were/are into this genre.