Tear Jerker / Randy Newman

• "Living Without You." It's one of his oldest, but still one of his most somber.
• "God's Song (That's Why I Love Mankind)", about God being evil and inflicting suffering on humanity just so we'll need him, while mocking believers worshiping him after doing that. Pretty hard to hear for many, even atheists.
• "Sail Away" doesn't seem like this at first. In fact, it sounds downright lulling... until you realize it's about a slaver pitching life in America to a group of native Africans.
• "When Somebody Loved Me" is easily the saddest thing he's ever written, and not only because of what it accompanies.
• "Losing You." Made a thousand times worse when it was used in the trailer for Toy Story 3.
• "Sandman's Coming", Margaret's final aria (and the penultimate number) in Faust. The dark lullaby feel is bad enough on its own, but it slides headlong into Fridge Horror when one remembers the context.
• "In Germany Before the War".
• "Marie," "Guilty," and "A Wedding in Cherokee County" from Good Old Boys can all feel very poignant.