It would probably have hit hard enough anyway, but I first heard this song on the radio soon after a friend suddenly died completely out of the blue of unknown cause, leaving a wife and two kids age about 2 and 5. It was actually 10 years ago this weekend, as it happens.
I don’t think two threads on the same topic in 20 years is too many.
Israel Kamakawiwoʻole’s rendition of “Somewhere Over the Rainbow” will get me every time.
As for purely instrumental choices I would add the climax from Barber’s Adagio for Strings
Warren Zevon - “Keep Me In Your Heart For A While”. After he got his terminal cancer diagnosis, he managed to get one more album out and this is the last song on that last album. Just absolutely heartbreaking.
Phil Hartman singing “Goodbye” during his final Saturday Night Live with Chris Farley sitting there sobbing is really hard for me to rewatch knowing both of them would tragically die with in the next four years.
Jim Stafford has a talking-song version of “Mr. Bojangles,” that is quite moving. Near the end, he becomes Bojangles and when he says the line, “Why is it a dog only gets to live a short time but he still has to die old?” I just lose it.
The Fifth Dimension — “If I Could Reach You.” Marilyn McCoo can sing the pants off me and no one needs to see that. One of those songs that makes you wish you were a girl so you could sing it in public — like Janis Ian’s, “At 17.”
These three always do it for me:
Even lighthearted songs by Karen Carpenter choke me up.
And as I grow older, One By One from Enya:
“One by one the leaves fall…”
I’m by no means a big Keane fan but this song:
gets me with just the first few notes.
Tracey Thorn made a Xmas album a dozen years ago. The song Joy, which she wrote, makes me weep.
I think the choice of music here is always going to be very personal and very reflective of emotionally-charged memories. It’s not just going to be about sad songs – it’s going to be about music that moves us deeply for whatever reason.
One candidate that I thought of proposing was “In the Wee Small Hours”, originally by Frank Sinatra but I prefer the Carly Simon version:
But what really triggers my emotions even more is a lot of Christmas music, because of such powerful associations. Some go right back to my childhood, but the most recent Christmas memories are evoked by Kenny G …
I’ve always loved that song, and teared up over it, and I’ve always been equally perplexed why the hell anyone would sing it at a wedding!
Omg, yes. I can’t listen to it without bawling. Yes, bawling.
“Whenever rain appears, it’s really angel tears.”
That is a good one that also gets me! I have an “Enjoy Every Sandwich” sticker on my dual-sport motorcycle because of him. That is freaking outstanding advice from a dying guy. 
Cat’s in the Cradle by Harry Chapin
Wreck of the Edmund Fitzgerald by Gordon Lightfoot
Fields of Gold by Sting
The last two verses are especially poignant.
Fast Car - Tracy Chapman
I Can’t Make You Love Me - Bonnie Raitt
Songbird - Fleetwood Mac (mostly because it was my mom’s favorite song)
I’m a sap. I can’t listen to any version of Ashokan Farewell without tearing up.
Meadowlark from “The Baker’s Wife” does me in.
Les Miserables: “I Dreamed a Dream” and “Bring Him Home”
Two songs about growing up and leaving home: Mary Chapin Carpenter’s “Only a Dream”, and Tom Rush’s “Child’s Song”
And also
I’ll never forget the first time I heard this one back in 2000. It was coming from a kiosk in a pedestrian tunnel in Moscow. I was looking to buy some comic books for my daughter, and I ended up getting the cassette as well.
Back in 2022, I put this one on and cried my eyes out when I heard that Judith Durham had passed away.
