Possibly a cool idea, possibly very boring. Your mileage may vary.
It all started when I observed that i) the frequency of those "iPod shuffle fic anthologies" seems tightly correlated with the cheerfulness of the fandom as a whole (e.g. despite having roughly comparably-sized samples on ff.net, the Zelda fandom has far fewer than the pokemon fandom) ii) a fic which is an iPod shuffle fic anthology... thing seems slightly more likely to be focused on interpersonal relations -- particularly shipping -- than a fic that is not.
Which led me to note that, any playlist I might assemble for such a hypothetical anthology would be hilariously unsuited to expectations i) and ii). I am pleased to say iTunes did not disappoint.
- John Cale, Fear is a Man's Best Friend
- Dire Straits, Industrial Disease
- Janet Baker (Gustav Mahler), Des Antonius von Padua Fischpredgit
- 梶浦由記, Rain and Storm
- Slim Dusty, One Truckie's Epitaph
- Joan Baez (John Prine), Hello in There
- Tom Waits, Murder in the Red Barn
- Warren Zevon, Play it All Night Long
- Kate Bush, Under Ice
- 梶浦由記, M03
- Jacques Brel, Les Singes
- Gordon Lightfoot, The Watchman's Gone
I don't see many of these songs as particularly "dark" or "dreary" (John Prine, Tom Waits, John Cale and Kajiura Yuki's M03 are probably the only ones I'd put firmly in the "dark, gloomy stuff" box), most have a sense of humor or irony about them that prevents them from being really at all depressing or scary, but neither are they in any way cheerful (except maybe Rain and Storm, depending on your feelings about rainstorms).
But of more interest is how completely this avoids (ii). What are the odds, I wondered, of managing to avoid love songs for twelve consecutive tracks? I was under the impression that, oh, maybe half of all songs are love songs? It's certainly a wildly popular topic. So, here's something to try. Run shuffle and skip through tracks, keeping count of how many consecutive non-love songs you come across. Once you come to a love song write down your count and start again from zero. Take the average of twenty or so such runs (or a larger sample if you have more time). What number did you get, do you think it accurately represents your musical tastes? I got an average of 4.8, so a chain of twelve songs like this is probably very unusual for my library.