'Closer' also reminds me of college follies, but it's skippable. The Downward Spiral is a great, atmospheric album that would be great background.
My many gig Led Zep playlist was fun except I should have left off the BBC sessions. The heavy guitar riff tracks are hot!
I would love to try out some trip hop but none one seems to loves it like I do. Stuff like Morcheeba and Portisthead is subtly sexy. Same for some more shoegaze music like Air.
Alternately if I wanted to truly relive awkward teenage awakening, it would have to be The Smiths/Depeche Mode/The Cure/New Order. Ah....the memories!