I would _not_ take one of my favorite albums, as I have them both memorized -- _Wish You Were Here_ and _Animals_. Ditto _DSOTM_. I think I might take some classical music, since I don't find most pop music intellectually challenging enough for repeated listenings for the rest of my life.
But I actually have been stuck on a dessert island (Hawaii) for 5 weeks once (on business, original plan was two weeks, and it kept getting extended), and I had only brought about 30 CD's with me, and the one that got _far and away_ the most listening was Tear Garden's _Last Man To Fly_ (I even got to the point where I started figuring out the programming feature on my portable CD player and sequenced it backwards). But I just about have that one memorized, too, although I would need a refresher before I left...
So I would probably pick an album based on the artist's reputation, but which I haven't heard yet. So, not knowing what's in store next for godspeed you black emperor!, and since I haven't heard _I Poopoo On Your Juju_ by Third Eye Foundation (his/their latest album), yet, I would probably pick that...but then I think about those wonderful instrumentals on _www.pitchshifter.com_...no, pretty much got that memorized, too...I've only heard Hooverphonic's _The Magnificent Tree_ once, and, funny coincidence, I had just pulled that out to listen to again, so maybe that...no...
Ask me again when I'm more decisive...no, that's not the problem, I'm pretty decisive right now...yeah, but I could be more decisive...(spontaneously combusts)...