I've got a few that are really depressing to me, that may not be for other people. First and foremost:
This one may be especially strange to some (many? most?), so allow me to explain: I always listened to a little bit of Tiny Tim for the novelty. You know - chilling and listening to "Livin' In the Sunlight, Lovin' In the Moonlight" or "Tiptoe Through the Tulips", appreciating the strangeness, whimsy, and fanciful nature of the tracks. I was looking for a good "pick-me-up" album after a rough stretch, and chose to download this thinking, "Oh, joy! This is ukulele-laden bliss, and it will pick me right up!" Perhaps it was just my mindset at the time, but that wasn't the case. I found that it made me overwhelmingly sad. What I saw the album for was this: Tiny Tim adopted this persona deliberately to have the naivete and wide-eyed wonder that a child has. It's the world as seen through the eyes of a child, is basically what I'm saying - you probably gathered that, but yeah. In addition, even the covers took on a whole different effect for me, listening. Anyway, certain tracks especially troubled me, as I saw the album from that perspective. Several of these will be included below.
And, Hell, even: