Okay, here's a first pass at a playlist. Got it to work on my iPod, and it seems to be okay... I would like to branch out further and add more. Some of the events so far have helped to shape the list.
1. "Lost Carol" by Akira Yamaoka, Silent Hill 3 Soundtrack (An introspective moment)
2. "Totentanz" by Maksim, Variations Parts I and II (Theme from Paridon)
3. "St. Jarna" by Depeche Mode, Little 15 Single (Ada's Song)
4. "Vampire Hunters" by Wojciech Kilar, Bram Stoker's Dracula Soundtrack (The Paridon Constabulary)
5. "Edward Scissorhands: Suburbia Barber" by Danny Elfman, Music for a Darkened Theater, vol. 2 (The Gnomish New Year)
6. "Mission Impossible: Trouble" by Danny Elfman, MfaDT2 (The Careening Carriage)
7. "Sickness unto Foolish Death" by Akira Yamaoka, SH3 (Investigation)
8. "Edward Scissorhands: Main Titles" by Danny Elfman, MfaDT2 (Kindness of Strangers, Sasha's Kiss)
9. "Lucy's Party" by Wojciech Kilar, BSD (The Mind of a Pet)
10. "To Die For: Main Titles" by Danny Elfman, MfaDT2 (Alek's Suite)
11. "Gave Up" by Nine Inch Nails, Broken/Fixed (Edditomas' Song)
12. "Batman Returns: Trouble Suite" by Danny Elfman, MfaDT2 (Stop! Police!)
13. "Freeway: Main Titles" by Danny Elfman, MfaDT2 (The World Makes Less Sense Now)
14. "Flower Crown of Poppy" by Akira Yamaoka, SH3 (Clocktower)
15. "Self Destruction, Part Two" by Nine Inch Nails, Further Down the Spiral (Ending Credits... and the song strangely covers a lot of what has happened)
I'd definitely want to add PC theme music as well... Any suggestions?