I think it pertinent, also, to think of what might've been Jess' favourite music, as I think 1) Sam is the kind of guy who doesn't live his life immersed in music (unlike his brother) and would therefore just listen (and shrug glibly and say stuff like "Yeah, it's alright, I guess") to whatever the people around him are listening to, and 2) he's also the kind of guy to have a few songs on his iPod that remind him of his beautiful lost love.

I wonder if Jess was a Tori Amos kind of gal or more into Madison Avenue? :)