The Decemberists/Tear Jerker

"There's a bend in the wind and it rakes in my heart. There's blood on the thread and it rakes in my heart!"
 * "On The Bus Mall". Soaring acoustic guitars + story about teenage runaways in love turning to underage prostitution to survive = utter uselessness on many a person's part.
 * That goddamn chorus. "But here in our hollow, we fuse like a family/but I will not mourn for you." Gets this troper every time.
 * Three words: "But oh, Valencia..."
 * From the same album, "You'll Not Feel The Drowning" and "The Crane Wife 1 & 2" can be quite depressing.

""And at the gate of the embassy Our hands met through the bars As your whisper stilled my heart No, they'll never catch me now""
 * "After the Bombs." Two lovers imagining life after war's end.
 * A whole crapload of songs that Colin Meloy has written can make people cry, most notably (in chronological order) "Odalisque", "Grace Cathedral Hill" (the line "We were both a little hungry, so we went to get a hot dog" might be especially triggering), "Red Right Ankle", "Eli, The Barrow Boy", "The Bagman's Gambit", especially the lines

""And as the waves came crashing down He closed his eyes and softly kissed her""
 * "Sons and Daughters" can make people cry bittersweet tears, as it's about a family escaping a war torn country.
 * Now from The Hazards of Love, we have the last two songs, where
 * "My Name is Leslie Anne Levine, and I've got no one left to mourn for me..." can really hit some people where it hurts.
 * "The Hazards of Love 4 (The Drowned)" is another one. Especially these lines:

""And I've written pages upon pages trying to rid you from my bones.""
 * "The Engine Driver" yet? This line, oh my god:

""I'm an engine driver, on a long run, on a long run Would she were beside me, she's a long one, such a long one.""
 * The whole song is a tearjerker, (in a more surreal and beautiful way than most of the other examples here.) because the passion and the sadness of the 3 narrators comes across so clearly:

""I'm a moneylender, I have fortunes upon fortunes. Take my hand for tender, I am tortured, every tortured.""
 * The first verse sounds like it's about the Engine Driver missing his wife/girlfriend while on the job. On first hearing the song, though, I interpreted it as the engine driver, who has retired, missing the train or truck or whatever he drives, since it would be so odd to can a real woman "A long one."
 * I perceived this as the Driver missing his love, but also being so isolated from everyone that he no longer differentiates between characteristics desirable for people and characteristics desirable for objects. So his love becomes "a long one", because that's the kind of route he likes best - he has no other frame of reference to draw upon.

""And it's one-two-three on the wrong side of the lea What were you meant for, what were you meant for? And it's seven-eight-nine, you get your shovel back in line And if you ever make it to ten you won't make it again.""
 * Again, there are two ways to interpret this: The sweet way, where the moneylender considers his fortune worthless compared to someone's love (I.e., hand in marriage.) Or, the deals that made his fortune, sealed with a handshake, may have been less than savory, and he's tortured by the memory.
 * "Yankee Bayonet (I Will Be Home Then)", about the American Civil War soldier and the woman who knows he won't be coming home alive, is another one.
 * Then there is "The Crane Wife 3".
 * "And I will hang my head low..."
 * "Sleepless", released on an album sold to promote AIDS awareness and possible to interpret as being about someone dying of AIDS. Even if that's not what it's meant to be about, it's heartrending.
 * "I Was Meant For The Stage" is sad enough, but try listening to it after losing an actor friend to suicide. *sniff*
 * From the latest album: "Please Avery... come home...".
 * "Rox in the Box" too:

""Hey Henry, can you hear me? Let me see those eyes. This distance, between us. Can seem a mountain size.""
 * In Pembroke City, when I was young, I lived by the castle keep/ And twenty-five pennies is all I earned to work as a chimbley sweep ... The Lyrical Dissonance and sudden verge into Squick in the final verse only make matters worse.
 * "Odalisque". Poor woman never had a chance.
 * After watching the video for "This Is Why We Fight", this troper decided he needs to just stop watching Decemberists videos. Man.
 * Rise to Me, a song about Colin Meloy's autistic son Henry, is both Tear Jerker and Heartwarming.

"His mother wept no tears, his brother grew unruly His mother wept no tears at burying Davey, at burying Davey Who'll plane the old pine boughs, who'll set his legs uncrooked? Who'll plane the old pine boughs? A coffin for Davey, a coffin for Davey!"
 * When The War Came. When this troper read the story behind it (group of scientist during the Leningrad siege, who rather starved to death than eat seeds from the seed bank they were guarding. And Nikolai Vavilov, geneticist who fouded the seed bank have died in a prison for not believing in Lysenkoism.), she bawled for an hour.
 * My Mother Was A Chinese Trapeze Artist makes this troper cry, for some reason. Despite that it was written to make someone laugh. Just the fact that the narrator goes through life largely unwanted ( 'Till the money got tight and they bet me away) and watching from a distance as everyone else has a lot more fun (look at his sister!), and the heartbroken tone of the original version... Ahem. There's something in my eye.
 * Burying Davey.