I actually did have to pull over once for that reason. My wife was playing a Disney greatest hits CD, and it got to Sarah McLachlan’s “When She Loved Me,” from Toy Story 2. At the time, my mother had recently passed away. The lyrics just reminded me so strongly of her, and the fact that she was gone now, that I almost completely lost it.
To this day, that song still gets me.
This song really got to my dad too, but in a totally different way. He would laugh like a hyena whenever it came on. He would poke me and say, “Get it? Get it? Because HE DIED!!! HAHAHAHA!!!”
He thought that song was the most hilarious thing ever, and while I can’t say he ruined it for me because I never really liked the song, I now LOATHE the song whenever I hear it, which is thankfully rare these days.
As for emotionally intense songs for me, I guess I’ll go with Kris Kristofferson’s Loving Her was Easier than Anything I’ll Ever Do Again. I’ll just zero in on these words:
I don’t know the answer to the easy way she opened every door…in my mind.
But dreamin’ was as easy as believin’ it was never gonna end.
And loving her was easier than anything I’ll ever do again.
I’ve said it before on this board, but it bears repeating. Kris Kristofferson was a poet without equal.
I had a similar thing happen with Lucinda Williams’ “Copenhagen”. The song is about her being in Copenhagen on tour when she finds out about the death of a close friend back home. I was listening to the album that the song is on about three weeks after my mom passed away and when that song played it hit me hard.
I heard that once, when I saw the movie. You can bet I’m not going to let it happen again! 
My entry is Can We Still Be Friends? by Todd Rundgren. The funny thing is, it’s not connected to anything in my head, and it means nothing to me. But something about the situation described and the notes of the music breaks my heart.
Woah, dad had quite a dark sense of humor.
A few songs that pack an emotional punch:
“I’ll Be Seeing You (in all the old familiar places)”
- originally by Billie Holiday, but since covered by just about everyone
“In the Wee Small Hours”
- originally by Frank Sinatra
“One for My Baby”
- originally by Frank Sinatra
“Long, Long Time”
- Linda Ronstadt, and very effectively used in The Last of Us
And on a happy rather than melancholy note, one of the most cheerful songs ever with the happiest memories is …
“Christmas Vacation”
- the opening theme song from National Lampoon’s Christmas Vacation, sung by Mavis Staples.
Two songs do it for me. First, the Bruddah Iz (Israel Kamakawiwoʻole) version of What a Wonderful World. I always liked the Louis Armstrong version, but Bruddah Iz’s cover just hit me. The second one - a bluesy cover of He Ain’t Heavy, He’s My Brother - has more of a story to it. My brother and I were ski instructors and carpooled to the mountain during the winter. Just a few weeks after the end of the 2018 season, he died of a massive heart attack. We were close, and I struggled mightily all summer, grieving and coping with his loss. On the first day of ski season the next year, all the ski school instructors took a commemorative run for him before our work day started, so it was already an emotional day for me. Then at the end of the day, as I’m pulling onto the main highway from the resort access road, He Ain’t Heavy… came on the radio, a blues version I’d never heard before. With the opening line (“The road is long…with many a winding turn…”) it seemed to be describing exactly my situation, since I was hitting a winding mountain road for a 2-hour drive. The gravity of it just hit me like a ton of bricks, and I had to pull over as tears streamed down my face. I wish I knew who the artist was.
World O World by Jacob Collier.
A vocal piece that breaks into 8 and 9 part harmonies in many places.
It gets to me every time…
T
Shortly after my wife died I was listening to some of my CDs at work and one of the songs that came up was a song where a husband is telling his wife how he’s found someone else. It wasn’t until the last verse when we find out that he’s at her grave.
I completely broke down, to the point where I was unable to continue working, and told my manager I needed to go home. She was very understanding.
Fortunately, I have completely forgotten who the singer or the song was. I remember taking the CD home with me and burying it somewhere in my country CD so I wouldn’t accidentally play it at work again. All I can remember is that it was one of my favorite singers, so I’m kind of sad that I may not be able to listen to that particular CD again.
Solitude by Black Sabbath. A sad-sounding song with depressing lyrics.
James Taylor - Fire And Rain (BBC In Concert, 11/16/1970)
Simply a singer, a guitar and a song he wrote when he was 22.
That was 55 years ago - and this will never be forgotten.
Adele - Someone Like You (Official Music Video)
Another classic proving you only need a talented singer-songwriter and a piano.
Elton John - Border Song (BBC In Concert 1970)
Again just a singer, a piano and genius lyrics:
Holy Moses, let us live in peace
Let us strive to find a way to make all hatred cease
There’s a man over there, what’s his color? I don’t care
He’s my brother, let us live in peace, oh
For me it’s “Windsurfer”, from the same album. One of the best songs about unrequited love ever. I was the guy in the song several times, until I met Ms. P.
It’s a great song.
“Winter” by Tori Amos and “Hurt” by Christina Aguilera (which isn’t the same as the NIN/Johnny Cash song) both hit me hard because they remind me of my dad.
“30KFT” by Assemblage 23
The other “Hurt” (the Johnny Cash version) but mostly the video, which is heart-wrenching.
“Space City” by Drive By Truckers (written by Mike Cooley) destroys me every single time. It’s from the perspective of a man dealing with the death of his wife and Mike just absolutely inhabits the character.
“That’s Life” by Paul Thorn. The lyrics are all things his mother said to him through the years. I played it at my mother’s graveside service. It brings her loss and memory back so intensely.
“If We Were Vampires” by Jason Isbell. It’s a reflection on the idea that if you’re married long enough one of you will end up alone. Tears me up as my wife and I watch the years pile up.
A newer one is “You Without Me” by Brandi Carlile and Elton John on their recent album together. It’s about watching her daughter come into her own as a person and become her own person. My twin boys are starting their senior year of high school soon and every kid growing up song is pretty much killing me these days, but this one just stabs me in the gut because Brandi’s vocal is so raw and pure.
Good luck. You did inspire me to check out 5 versions on YouTube, including soul versions by Donny Hathaway, Al Green, and David Ruffin. But oddly the one with the most blue notes was the original 1969 version by Kelly Gordon. Probably not it…
Moby “Slipping Away” and its video, during a rough pregnancy with complications for Mrs G and our daughter.
I came here to nominate that whole Little Earthquakes album, but for some reason, “Mother” gets to me the most. For the uninitiated, it’s about the lost identity that many women experience when they get married.
Go, go, go, go, now
Out of the nest, it’s time
Go, go, go, now
Circus girl without a safety net
Here, here, now, don’t cry
You raised your hand for the assignment
Tuck those ribbons under
Your helmet, be a good soldier
First my left foot
Then my right behind the other
Pantyhose running in the cold
It’s not even something it occurred to me to be emotional about until I heard that song. And then I was like, shit, that’s just how it is, isn’t it? All that grief and longing and fear packed into one song.
Oh, wow, yeah. I’ve listened to that song a lot of times but never really listened to it.
That whole album is a gut punch. I never got into the rest of Tori’s work (except for “Happy Workers,” from the movie Toys, which is what brought her to my attention originally) but that album is amazing.
There are a few that I’m sure I will remember later. One that sticks out was more about the timing but the lyrics still get me. When my father died they quickly got me on a plane from Germany on emergency leave. After I got home I was laying in the dark listening to music and I heard “Time Stand Still” by Rush.
Summer’s going fast, nights growing colder
Children growing up, old friends growing older
Freeze this moment a little bit longer
Make each sensation a little bit stronger
Experience slips away
Experience slips away
The innocence slips away
She sang an early version of it but was not the original. Bing Crosby had a number one hit with it the same year. I’m not sure which came out first. Sinatra sang it years before. Looking at wiki it’s says the song was actually from a failed Broadway show that closed after 15 performances.