For me, it’s “The Rose.” And I don’t even much like Bette Midler. Even so, it’s been a good deal more than one or two times it’s reduced me to tears and utterly destroyed my macho facade.
So let’s hear it. What breaks you up and exposes all your hidden beautiful feelings to the jeers and mockery of your brutish ape-like compadres? Surely I’m not alone here!
Randy Crawford - “One Day I’ll Fly Away”
Hardly floods of tears, but it was all around at the time of a painful break-up, and it can still shake me up decades later, especially if I hear it unexpectedly.
The Dance. Garth Brooks.
Alison Krauss’ version of “I’ll Fly Away” always gets me even though I don’t believe in an afterlife.
Lots of them, actually.
Aaron Espe - Back to the Beginning, for the most recent one. It inspired me to start a thread about songs that hit too close to home on several levels.
Don McLean - Vincent
But I could have told you, Vincent
This world was never meant for one
As beautiful as you
Let’s stop here (for the moment).
Alison Krauss has a truly moving voice.
Alison Krauss & Union Station — “The Lucky One” — Live - YouTube
And two from the Lord of the Rings:
The Lord of the Rings: The Fellowship of the Ring • May It Be • Enya - YouTube
Annie Lennox - Into The West (live at the 2004 Oscars) - YouTube
I don’t know about “mawkish”, that’s a bit pejorative, but I embrace sentimentality. Who doesn’t want to be moved in that way?
“one day I’ll fly away” is a good one.
“good year for the roses” Elvis Costello version
“Devonside” by Richard Thompson, the live version specifically.
This verse gets me every time.
Ah, she said, my John, I’ll be your pillow
I’ll be your lover, mother, whore and wife
And he knew that he had loved and never seen her
When the light fell from the shiver in her eyes
I listen to this one a lot late at night, especially in the depths of winter:
I would be happy just to hold the hands I love
on this winter night with you.
It’s not exactly mawkishly sentimental, Danny wrote this song after his mother died and I cannot listen to it without having at least a sniffle.
I’ve told you not to call me Shirley!
OK, with that out of the way, “Alone Again, Naturally” has to rank #1 in this category.
Harry Chapin’s “Taxi” and “Sequel,” back to back.
The story of two people, who seem just right for each other, except she’s a society girl, and he’s just a cabdriver. They’ve met before, and “learned about love in the back of a Dodge,” but that was that. The girl was gonna be an actress, and Harry was gonna learn to fly, but all that happened was that “she took off for the footlights,” and Harry took off for the sky.
Except neither’s wish came true. She ended up acting happy, inside her handsome home; and Harry just kept driving a taxi, taking tips and getting stoned. He goes flying so high …
It’s in “Sequel” where the tearjerking comes. Sue got away from her rich family, and now lives in a five-storey old brownstone. Harry has had some success with music, and is now doing concerts, and he pays a call on Sue, when he’s in town for a concert. They converse, and when asked by Harry “Why are you so happy now?” Sue replies:
I finally like myself,
At last, I like myself.
Have the Kleenex handy. That’s when we understand who Sue really is, and she’s not that society girl, nor did she ever want to be. That was a role that was thrust upon her.
I used to sing both these songs back-to-back, at a neighbourhood pub, back in the 1990s. And it was difficult, I must say. Just so much emotion in the lyrics.
“Somewhere Over the Rainbow.” It was played at the funeral of one of my students, as it was her favorite song.
“Saturn” by Sleeping at Last:
You taught me the courage of stars before you left
How light carries on endlessly, even after death
With shortness of breath
You explained the infinite
And how rare and beautiful it is to even exist
I don’t know if I’d call either of these “mawkish” but they certainly are sentimental and get me every time.
“Space City” by Drive By Truckers (written by Mike Cooley. “If I could have one wish right now, I’d be about half as tough as I pretend I am.”
“Elephant” by Jason Isbell “Surrounded by her family I saw that she was dying alone”.
Believe it or not, the song “Patches” by Clarence Carter gets me choked up a bit. Even though some people consider it the corniest song in existence.
One Tin Soldier, by Coven.
Shut up! 
For some reason “I’ve Been To Town” always made me maudlin. It was first a poem by Rod McKuen, then first sung by Glenn Yarbrough, who could make you cry by singing the phone book. This part of the lyric always got to me:
"Don’t tell me any more lies
I can’t waste any more years
I’ve seen my image in your eyes
dissolve in disappointed tears.
I’ve been to town you ask me do
I know the Milky Way
I do and furthermore I’d like to say
It isn’t milky white it’s dirty gray.
Especially when
Your world breaks down
I know because
I’ve been to town…"
That was a collaboration with Gillian Welch (first featured in the film “Oh Brother, Where Art Thou?”).
My choice would be a Gillian Welch solo song (well, with David Rawlings): “Hard Times.” The sentimental feelings are for…a mule. Don’t laugh. It’s a real tearjerker (for me, at least).
Cry? Can’t think of one. Emotional, with a swelling in my chest, and feeling like tears aren’t out of the question? Maybe these ones, but I’d never describe any of them as “mawkishly sentimental.”
Harry Nilsson’s cover of Randy Newman’s “I’ll Be Home”
Bruce Springsteen’s “Valentine’s Day”
The sax solo in Paul Simon’s “Still Crazy After All These Years”
Okay, maybe this one’s a bit mawkish. I was in a pretty emotional place when I saw “We Wil Rock You” at the Dominion in London, but I was nearly brought to tears by “No One But You”
Several song over the years have brought a tear to my eye but The Sad Cafe by The Eagles does it for me almost every time. Some friends and I used to use a local truck stop as a hang out and as our numbers dwindle I can relate to that tune.
Gordon Lightfoot, “The Wreck of the Edmund Fitzgerald”
Does anyone know where the love of God goes
When the waves turn the minutes to hours?
And all that remains is the faces and the names
Of the wives and the sons and the daughters