My high school drama teacher taught our class The Circle Game and had us sing it during the last week of school. One girl, who was graduating that year, burst into tears and ran out of the room.
It was a song at the end of an episode of ‘The Wonder Years’ - I seem to remember Kevin’s grandfather, and I think a dog. I’d never heard the song before but the combination made me tear right up.
Cat’s in the Cradle is by Harry Chapin (as noted earlier). But I’ll add Father and Son by Cat Stevens to the list.
Mawkish? Not sure. But yes, absolutely, and I can’t think of another song which makes me cry. I’m a sucker for the June Tabor version
Oddly, I’m OK until she starts singing Waltzing Matilda, but that does for me.
j
I always get those two mixed up (they were both fine singer-songwriters from the same era. Both good songs, too). You’d think “Cat” Stevens should have written “Cats” in the Cradle, however!
There’s A Long, Long Trail A-Winding
Oddly enough, none of the professional recordings move me at all. But get a group of non-professionals singing it, and it is heart-wrenching.
As the cast of MASH demostrated.
Quoting rather than reposting.
I feel like I did this not too long ago, but here are mine both related to my son’s death:
If I Die Young - The Band Perry
Lord make me a rainbow, I’ll shine down on my mother
She’ll know I’m safe with you when she stands under my colors.
Oh, and life ain’t always what you think it ought to be, no
Ain’t even gray, but she buries her baby.
The sharp knife of a short life
Well, I’ve had just enough time.
Wherever You Will Go - The Calling
And maybe, I’ll find out
A way to make it back someday
To watch you, to guide you
Through the darkest of your days
I know now, just quite how
My life and love might still go on
In your heart, in your mind
I’ll stay with you for all of time
Look up “The Cat Carol” on YouTube. I think the song was written with the goal of jerking as many tears as possible.
Re Rainy Days and Mondays
It made me think of how I feel when hearing Todd Rundgren’s Can We Still Be Friends. I have no associations with the song, it means nothing to me. But something about the music is just heartbreaking.
I’ve liked the song Monday, Monday since I was a kid. It helped lift my spirits having to go back to school after a fun weekend.
I forgot a couple of songs that were used to devastating effect in Scrubs. Divorced from the show, I don’t think they hit quite as hard, but they’re still pretty effective:
Colin Hay’s “Waiting for my Real Life to Begin”
Peter Gabriel’s “The Book of Love”
Three submissions:
Last Kiss - J Frank Wilson & The Cavaliers
Seasons in the Sun - Terry Jacks
[‘Shannon’ was a dog. That right there is kryptonite for me]
I need a tissue now 
“I Was Young When I Left Home” - Antony
“Watermelon in Easter Hay” - Frank Zappa
I’d forgotten, “Waiting…;” that is a beautiful arrangement.
And probably the most touching Dr. Cox line of the series.
I do not cry. I may feel very emotionally affected by a song, but crying? Not my thing.
That said, I recently saw a video of Willie Nelson singing Yesterday When I Was Young with pictures of him from throughout his life, and wow.
Similarly, the video of Johnny Cash singing Hurt near the end of his life.
Does “Thirteen” by Big Star count as mawkishly sentimental? (I’m not sure I’d call it “mawkish” but definitely sentimental.) Every time I hear it, it just takes me back to my childhood and young crushes. It’s such a poignant, soul-stirring song.
Won’t you let me walk you home from school?
Won’t you let me meet you at the pool?
Maybe Friday I can
Get tickets for the dance
And I’ll take you, ooh-ooh
Ah, jeeze, yes. And the last song from that album, “Come On, Come On”, always gets me choked up. For that matter, so does her “I Am A Town”, which makes me think about all the little North Carolina country towns I drove through, visiting family.
I fixed a typo in your quote - her name is “Mary-Chapin Carpenter”.
F-ing autocorrect! Thanks for fixing it!
“The Dance” was one of my wife’s favorite songs (along with a few of Garth’s others) and every so often when I hear it I start thinking about her. In fact, it seems to have gotten a bit dusty in here. Oh, and the Judds’ “Mama He’s Crazy” because she said it was about us.
There are a lot of songs that will make me misty-eyed, depending on my mood when I hear them. George Jones’ “He Stopped Loving Her Today”, Bette Midler’s “The Rose”, and a bunch of others that I’m trying not to think of.