The end of Bringing Out the Dead. “Nobody asked you to suffer. That was your idea.” Man, I love that movie.
This is my grandfather. Down to the last detail; the glasses, the tweed jacket, the pressed pants pulled suspiciously high, the white hair and the slightly straggly eyebrows and the blue eyes. He was one of the kindest, gentlest, most intelligent men I ever knew. He died in March 2008.
I had a bit of difficulty getting through the opening montage of Up in the movie theater when it hit me.
I tend to be a cynical sort (in the past, I’ve frequently re-applied Oscar Wilde’s “One must have a heart of stone to read the death of Little Nell without laughing” to one of the entries referred to herein), but I have yet to read Huckleberry Finn’s pronouncement “All right, then, I’ll go to hell” unblurred by moisture in the eyes.
I once had a girlfriend break my heart clean in two, and though I had watched it a bunch of times before, the part in (anime) End of Evangelion where Asuka activates her Eva and starts fighting back…after I had my heart broken, I can’t help but tear up by the time she says, “You were always protecting me! Always watching over me!” Have no idea at the connection there.
Also, when Dory from Finding Nemo says, “I look at you and…I’m home.” Write me off right there, I’m useless for the next few minutes.
For songs…that same girl introduced me to Minor Majority, and one of the things I did to get over her was put on “Wonder If She Knows” by them and bawl. If I dig at it now, I can still get teared up.
Oh, God - I know what you mean! Sometimes I walk around singing Dream a Little Dream to her and it makes me cry. It was the same song that used to comfort my little boy when he was a baby and it kills me to know that she’s growing so fast and soon I’ll have no one to sing that song to. I wish I could hold her forever to watch her eyes light up while she laughs and reaches for my cheeks while I’m singing.
I have to add another one. This week’s episode of Bleach, and the corresponding chapter of the manga:
About half the characters in this episode either die (but some get better) or end up horribly injured and/or traumatized. The death of Ulquiorra is the thing I specifically came to post about. He spends most of his time on the series alternately guarding and emotionally bullying Orihime, partly because it’s his job, partly because, as an Arrancar, he doesn’t understand her human emotions, especially her loyalty to her friends and unrequited love for Ichigo. It is only in Ulquiorra’s final moments that he understands that he, too, has emotions, and one of the last things he does is ask to hold Orihime’s hand. Being the compassionate girl she is, she agrees, and continues to do so as he turns to dust and blows away. I don’t know why this affects me so much, since he is a villain, but I think it ties in with what Sunspace wrote about striving to become human and experience love.
I’ve only read the manga chapter and seen screenshots of the anime, and it still makes me misty-eyed just typing this. If I see the actual episode now, I will definitely start to cry. 
You said entertainment, so here goes.
I was at a local yokel St. Pat’s parade and leading the parade was a group of developmentally disabled children. I had to hide my eyes in my sleeve.
The original short version of " Flowers for Algernon ".
People still watch Bleach? I really wanted to keep liking it, but the endless filler and the fight scenes that made DBZ look fast-paced… ugh. I got to the beginning of the 2nd Hueco Mundo arc I think, and gave up.
The Stand.
I just re-read this for the millionth time and still, every, single time when
Stu falls down the embankment and Larry, Glen and Ralph have to leave him behind. and
when Stu gives Tom the eternity symbol medal
M.O.O.N. That spells sobbing!
As many said:
Beginning of Up, Marley & Me, the part in Sixth Sense where the kid tells his mother about her mother…
Several songs, but the one that strikes me is Hallelujah, Jeff Buckley’s version. If I sing it myself, I can’t go through the entire song, but the worst thing is, I don’t know why. It just makes me tear up, and before long, I’m bawling.
This song by Sufjan Stevens about a girl dying of cancer and the boy who loves her.
Can’t listen to it.
Oh yes.
…
I didn’t read the thread because even reading about sad songs/movies makes me cry. But I did a search and see that nobody’s mentioned the movie Taking Chance. Kevin Bacon, escorting a Marine’s body home. Every time Bacon did that slow salute, I teared up, and again when he spent the night in a warehouse with the coffin instead of heading for a hotel. They underplayed the traditional tear jerking scenes, which made the other scenes even more effective, because you had to think about it, about what happened to that 20-year-old kid.
My family’s crying songs are Blind Man in the Bleachers and Country Bumpkin, and the Kathy Mattea song about the couple in the nursing home.
Ok, on a personal note, the song Second Chance by Shinedown.
Here are a few that I’m surprised no one has mentioned yet, when Roland watched Susan get burned at the stake in Wizard and Glass from the Darktower series by Stephen King, the movies My Life(with Michael Keaton) and Leaving Las Vegas(both excellent movies that I will never watch again), and Hello, Darlin’ by Conway Twitty.
One that also gets to me is Sam’s last words on the finale of Cheers, “I’m sorry, we’re closed”.
Movie: E.T. – when he apparently dies, and then when the flower begins to revive and you know he’s alive.
Song: My Immortal by Evanescence – just a beautifully haunting song.
Book: Lonesome Dove – Gus’s death.
Television: Buffy the Vampire Slayer – Mom’s death.
Oh my god. I remember seeing this in the theater and I was alone. I bawled my frickin’ eyes out. You made me remember…thank you. I’m in a bad place…maybe I should re-watch it and have a cathartic cry!
Oh…and a spoiler here probably would be good. I have not read the series but plan to someday. I’m sure I’ll forget by then but for others…
Oh yes. One of my favorite, favorite books. I first read it for a leadership class.
Just reading this thread brings a lump to my throat.
I’d forgotten about the short story, Flowers for Algernon, I remember reading it in high school, which was already kind of an angsty time.
I can never read The Yearling again.
I really had a tough time with the little girl in the pink coat in Schindler’s List.
I always tear up during Beth’s death scene in Little Women.
…“Now I am the one going ahead…”