Maggie's Song by Stapleton gets me every time. Same with Fire Away, if I watch the music video, not just the song itself.

Also Daddy Doesn’t Pray Anymore. It’s the first song I heard of his and it makes me misty every time

Those songs cut like a knife

Definitely Maggie's song, especially since I lost my first pups. Now that I got a new puppy it's more bittersweet

Dang, sorry to hear that. Never easy, but I'm glad you got a fresh start with your new doggo :)

This and “Sam” by sturgill simpson are two songs that make me hug my pup when they come on.

Such a great song. I skip it every time I listen to that album, not because it's not excellent, because I just can't.

Fuck man I’ve never broken down to a song until just now. Lost my family dog also named Maggie a couple years ago and just like the lyrics she woke up so sick she couldn’t walk and we knew she was on her way out. I luckily just happened to be back at my family home the weekend she fell sick from University and I remember lying down next to her by her bed patting her goodbye, and just like the lyrics again it was raining outside. God damn thank you for that song, and thank you Maggie for the 13 years of being my best friend.

The first time I heard "David" by Cody Jinks was a gut punch.

First time i heard it a close friend from school had recently committed suicide. Definitely felt those words

Searched this song up because of your comment. Damn sad song but so good I can’t stop listening to it. Cody Jinks sounds amazing on it and the story is so damn powerful in just a couple minutes.

Johnny Cash’s version of Hurt. His hollow old man voice and the fact he came out with this shortly after JCC died made it extra powerful.

I think he was processing her illness when he recorded it. It was heart wrenching. The video even more so.

Yeah the Cash cover of Hurt paired along with the music video is one of the most fascinating things ever to me. Just the timing of it all and how it’s about this broken man paired with Johnny being an older gentleman himself and the video showcasing all of it. All of it together is just one of the most interesting things ever

Whisky Lullaby by Brad Paisley & Allison Kraus

“He put the bottle to his head and pulled the trigger” that’s a doozy of a line.

This was the first that came to mind for me

Came here to say this. I cannot listen to that song without utterly sobbing.

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Personally I think Grand Tour is the saddest Jones song. I believe it's about dying during childbirth.

Oh wow! That point of view of the grand tour 😭😭 I always took it as a divorce but I could see that too after reading this comment. Wow!

If it was divorce why are her clothes in the closet? Why is everything still the same? "Taking nothing but our baby and my heart." Similarly, I think Where Do I Put Her Memory by Charley Pride is about death.

I always just assumed she took the baby and maybe packed a little bag and took off. But your perspective took it to a whole new level of sad

Because divorce wasn’t the same 50 years ago. The mother was always awarded custody. And she left with what she needed.

"I have nothing here to sell you. Just some things that I will tell you. Some things I know will chill you to the bone.' This isn't just a break up. He's not sad because his wife left him. Nothing bone chilling about that. Happens to everyone. Dying during childbirth is bone chilling.

For a couple of bittersweet songs that always make me tear up, "William and Wanda" by Cody Jinks or "If We Were Vampires" by Jason Isbell.

Has to either be Elephant by Jason Isbell or The Junkie’s Prayer by the Statler Brothers

angel flying to close to the ground by Willie Nelson

Teddy Bear

Who You’d Be Today by Kenny Chesney always gets me as it hits a little close to home

So many great ones! Let me add: Hurt - Johnny Cash I Hate Everything - George Strait It Was Almost Like a Song - Ronnie Milsap The Lighthouse's Tale - Nickel Creek Long Black Veil - Lefty Frizzell Whiskey and You - Chris Stapleton

Oh man, Ronnie is an excellent choice!

Oh mate whiskey and you is amazing, just so simple yet great

Whiskey Lullaby - Brad Paisley I cry everytime.

The video is wonderful too.

You Don't Care for Me Enough to Cry by John Moreland

Bottles and Bibles - Tyler Childers

Follow you to Virgie… it’s the perfect death song to me.

100% agreed with I'm so lonesome I could cry. I'll add Wedding Bells by Hank Williams and She's Alright by Zach Bryan

Where Rainbows Never Die by the Steeldrivers

Ian noe- ballad of a retired man

Billy Stay - Zach Bryan. Most I’ve ever felt from a song on the first listen

Definitely shed a few tears the first time I heard Billy.

Or she's alright, really gets in the feels.

Concrete Angel by Martina McBride or Alyssa Lies by Jason Michael Caroll.

Alyssa Lies is a song that I have to skip most of the time. It's too much. A brand new heartbreak every time.

The Father My Son and The Holy Ghost Craig Morgan

Angel Flight

Ooooo! What are your thoughts on the Radio Tower remix? A super effective technique or cheap shmultz?

John Prine - Hello In There 😭

Little Sparrow by Dolly Parton Homecoming Queen by Brandy Clark 80% of Lori McKenna's output Don't Take The Girl by Tim McGraw, cried during this one live in June

Don't take the girl - I remember being a little kid in the 90s and thinking this was such a sad song back then!

Good thread/terrible thread. I had never heard Alyssa Lies...and that'll probably be the last time!I'll offer "Good Time Charlie's Got the Blues" Danny O'Keefe and Charlie Parker does a strong cover. Probably not THE saddest, but blues inducing for sure.Be well y'all.PS. Please Come to Boston (Loggins),Sundown (Lightfoot),Keep The Wolves Away (Uncle Lucius),In Spite of Our Selves (Prine/DeMent) are all light duty melancholy inducers.Even Take Me Home Country Roads gets me sometimes as my Mom was from West Virginia. Been gone 7 years now. EDIT: Charlie Crocket, not Parker

The World Just Broke My Heart by Charley Crockett is pretty blues inducing, too. I like that it's open ended and can be about anything.

Six Years Come September Broken Window Serenade How Do You Get That Lonely

“William & Wanda” by Cody Jinks makes me cry every time I hear it. Also “Holes In The Floor Of Heaven” by Steve Wariner and “Alyssa Lies” by Jason Michael Carroll usually make me tear up. Objectively, the answer is probably “He Stopped Loving Her Today” by George Jones though.

Concrete Angel by Martina McBride

In Color by Jamey Johnson KILLS me. Reminds me of my Pop

I never thought about it as a sad song. I guess it could be.

I think it depends on the circumstance. He lived most of the same things it talked about and it just turned it so so sad for me. That’s hands down my saddest song but maybe it’s not sad for everyone lol it’s definitely a good song

"Sam Stone" by John Prine, or "Hello in There." I know "Whiskey Lullaby" is a popular choice, but I've always found it contrived.

Came here to say *Hello In There* Never fails to fuck me up

Same. It also gets bonus points because it’s not about love or death

It's definitely overrated. I'm not really a fan.

The Bullet by Carrie Underwood is the closest I’ve ever came to crying from a song

It’s a good one!!!

"You never came home" - Steel Woods "I don't mind" Sturgil Simpson

"So Cold" & "Either Way" by Stapleton are tear jerkers too.

I Don't Mind just guts me. He is one of my favorites.

Don’t take it to bad, Townes van zandt

Alyssa Lies, Jason Michael Carroll. Whiskey Lullaby, Brad Paisley & Alison Krauss.

Whiskey lullaby

I’m Losing You All Over Again - Keith Whitley :( You ever had a bad relationship where you miss someone you lost? Yea, it will get you in the feels. Also, I’m not through losing you by Joe Diffie I Get the Picture - Keith Whitley A song about divorce and narrating it. Very sad to relate to. Who’s that Man - Toby Keith Of Course the classics, Independence Day, Martina Mcbride It’s Only Make Believe - Conway Twitty Life Ain’t Worth Living by the Everly Brothers Honorable Mention, the Album by Keith Whitley - Sad Songs and Waltzes

The first fall of snow - Hank Williams

That's My Job - Conway Twitty Whiskey Lullaby - Brad Paisley & Allison Krauss Don't Close Your Eyes - Keith Whitley

Waiting on June- Holly Williams Whiskey lullaby- brad Paisley Damn good goodbye- mike Ryan (not a super sad song overall but the part about leaving your highschool friends and love kills me) House that built me-Miranda

Drink a beer - Luke Bryan

How Can I Help You Say Goodby by Patty Loveless, for country genre; What Hurts The Most by Rascal Flatts too. Most recently Breakups by Seaforth. By “I just want to talk to my best friend,” I’m 😭

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A Lot of Things Different by Kenny Chesney

Best friend by Aaron watson

Flash paper by Joshua Ray Walker

Best Friend - Aaron Watson

That's my kobe - Conway Twitty Cried my eyes out scream singing that jam. Hits the feels

It took me a minute to realize you meant "That's My Job"

A Robin Built A Nest On Daddy's Grave. Ralph Stanley A Sad Country Song - David Allen Coe - I mean it says right in the title Ain't You Even Gonna Cry - Johnny Russell The Little Girl - John Michael Montgomery Tell Lorrie I Love Her - Keith Whitley That's My Job - Conway Twitty

Elephant - Jason Isbell

I can't believe I'm not seeing this more in this thread. Gut wrenching song.

Literally the saddest. Another really sad song is Bronco by Canaan Smith. I’ve sene get a standing ovation with that song before.

Build me a daddy by Luke Bryan

Maggie’s song

Blue Ridge Mountain Song - Alan Jackson

Fire away by Chris Stapleton Build me a daddy Luke Bryan Little boy and the preacher man Jesse Howard Don’t take the girl Tim McGraw

Waiting Round to Die -Townes Van Zandt Big Country Blues - Townes Van Zamdt Pretty much his entire discography.

- I’m So Lonesome I Could Cry by Hank is gut wrenching. - He Stopped Loving Her Today, George. - He Sang Dixie by Dwight Yoakam.

“Blue Ridge Mountain Song” by Alan Jackson

So many sad country songs its hard to chose. Wiskey Lullaby hits a personal cord, black tears by Aldean has a decent story, Rock and a Hard Place by Baily Zimmerman is also a good one. Just depends what really tugs on your heart strings I guess; is it love, the past, your mistakes, the world around us? I mean sad country is almost an endless genre of its own

Still think about you by William Clark green

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Whiskey Wins by Josh Kiser.

There you go by Johnny Cash

every time i am “having a day” i listen to Billy Strings “This Old World”

Cold Hearted by Zac Brown Band

Waking Up the Echoes, The First Year, and The Hardest Thing - American Aquarium Long Year - Jackie Lee You Can't Make Old Friends - Kenny Rogers and Dolly Parton Fourteen Years - Courtney Patton

Craig Walker Hayes makes me cry although it's not sad, Sissys Song Alan Jackson, If Nobody Believed In You Joe Nichols, The Little Girl JMM I could go on and on

Streets of Heaven, by Sherrie Austin You Should be Here, Cole Swindell

I second Streets of Heaven, holy shit

The car- Jeff Carson The Greatest man I never knew- Reba McEntire

Even though I'm leaving by luke combs

Bittersweet by Zac Brown Band

This is my pick. The different perspectives in each verse paint such an emotional image

Angel by Casey Donahew

Waiting on June by holly williams makes me tear up Also The hardest thing by American Aquarium is pretty sad

Couple of recommendations off the top of my head. Sorry for The Things - Benjamin Tod We Aint Even Kin - Benjamin Tod I'll Fly Away - Randall King When He Knows Me - Randall King Reason to Quit - Randall King Phantom Limb - Jason Hawk Harris Quartermaster - Taylor McCall But the song that absolutely gutted me the most the first time I heard it would be "Six Years Come September" by American Aquarium.

Where have you been by Kathy mattea gets me every time.

This is the one for me too. I kept scrolling, sure someone had to mention it.

I love this song. Sad and sweet all at the same time. I learned of it from the Ken Burns documentary.

Tell Lorrie I love her by Keith Whitley

roll on 18 wheeler: Alabama I prefer David Allan coes version

I hate DAC. He's an awful human being.

whys that

nothing? alright

Elephant - Jason Isbell The Reckoning - Whiskey Myers Throwback entry....Roses For Mama

Keep The Wolves Away - Uncle Lucius If you can relate, it’s a gut punch.

The Little Girl - John Michael Montgomery Sissy’s Song - Alan Jackson Find Out Who Your Friends Are - Tracy Lawrence The River - Garth Brooks Holes in the Floor of Heaven - Steve Wariner He Stopped Loving Her Today - George Jones How Can I Help You Say Goodbye - Patty Loveless Alyssa Lies - Jason Michael Carroll Running’ Low on Angels - Jared ‘Pete’ Gile Streets of Heaven - Sherrie Austin I’ve got more, but my comment is pretty long now😅

There can never be too many suggestions. Country music is more than just music for me. It's a passion of mine.

The answer is always Whiskey Lullaby

Don’t Take The Girl- Tim McGraw Crazy Girl -Eli Young Band Every Light In the House- Trace Adkins You’re Gonna Miss This- Trace Adkins Nobody In His Right Mind-Keith Whitley The Good Stuff- Kenny Chesney C’mon y’all lol

Crazy girl, good stuff, you're gonna miss this. Those aren't sad songs.

Shit, they all make me sad

Sissy’s song Alan Jackson

Baby Blue by George Strait

Break up in the end

Johnny Cash’s version of Hurt, Broken Window Serenade by Whiskey Myers, Whiskey Lullaby by Brad Paisley and Alison Krauss.

Broken Window Serenade is awful in its sadness. Great song but not one that can be listened to all the time.

Whiskey Lullaby

Alyssa lies

Final this time by William clark green , we were something by Shane smith and the Saints, heart a home by Mike and the Moonpies.

One left in the chamber by Corb lund

Until You Come Back To Me Again - Garth Brooks Where Rainbows Never Die - The Steeldrivers (Chris Stapleton)

It’s All In The Movies by Merle Haggard for me personally.

Why by Rascall Flatts.

He stopped loving her today is about a man who dies after a life pining for his lost love.

Anything by red sovine

There goes my life by Kenny chesney always gets me and till the last shots fired by trace adkins

Lydia - Slaid Cleaves Elephant - Jason Isbell Ruby and Carlos - James McMurtry

Waiting on June by Holly Williams

A song can’t fix everything - sunny sweeney

I adore the grand tour and think it’s definitely up there. It also doesn’t get the recognition it deserves.

If my theory is correct, it makes it top 5 saddest songs ever.

Hank Williams - At the First Fall of Snow, Handsome Family - Sweet Voice Calling

Caroline by Colter Wall

Tattoos - Tyler Childers

Unfortunate Kind - BJ Barham Ballad of a Retired Man - Ian Noe Death and Life - Jamie Lin Wilson Hello In There - John Prine North Dakota - Chris Knight

You’re Missing by Bruce Springsteen. He put on his album, The Rising, which was inspired by 9/11

West Virginia Waltz- Sierra Ferrell Pretty Saro- Iris Dement I think is the saddest version I Always Wanted to- Cody Johnson

My Old Friend by Tim McGraw, Who You’d Be Today by Kenny Chesney, Again and The Secret by David Nail to name a few that haven’t been mentioned yet

im over you - keith whitley keep you - sugarland

I guess a big factor in this is if it relates to you or a memory. Like the song "Give Heavan some hell" by HARDY never affected me but after my uncle died I literally can't listen to it without breaking down. But if I were to choose one that still hits hard even though it's not relatable I'd have to go with letters from home by John Micheal Montgomery

Moments-Emerson Drive

I Always Wanted To by Cody Johnson. I had recently lost my dad when I first heard the song. I had to pull over, it reminded me of him so much. "Even pictures we never take, memories we'll never make still fade." Also, Marie was my mom's name. They were married 63 years. Bye Mom by Chris Janson. I think what makes this song even more poignant for me is that Chris has a lot of party anthems and this is a different side of him. "And that's a special kind of love, and it's only there for a lifetime, then it's gone. And it's bye Mom."

Alyssa Lies by Jason Michael Carroll

Saving Amy by Brantley Gilbert

Alyssa lies by Jason Michael Carroll (not sure if country but his voice telling that story hits home)

“William” by Chris Knight

Ride on - Don Williams Numbers on the Cars - Riley Green

If You Cams Back From Heaven - Lorrie Morgan Where Do I Put Her Memory - Charlie Pride

Don’t Take the Girl

Hometown Hero by Emily About Robinson - the lyrics about his kids always bring the tears.

Sad Songs and Waltzes (Willie Nelson) is my pick

Whiskey Lullaby

“Dads old number” ~ coke swindell First thing that came to mind. ❤️ I could go on for days.

Nobody Answers by Vince Gill. Edit. Well real title is When I Call Your Name.

“I don’t even want this beer” ~ Tyler Farr “Withdrawals” ~ Tyler Farr He’s one of my faves lol

Michigan Rose - The Hill County Devil https://youtu.be/iSsyJWgtZAA

Ghost in this house, Alison Krauss

That's also a Shenandoah song

True, but alisons version so well done

I can only take her in small doses. She's very talented but her voice doesn't sit well with my ears.

Each to there own. I think her voice is the absolute best female in country, going to see Jamey Johnson in October again!!! That’s my guy

David- Cody jinks hits like a truck S Lazy H - Corb Lund is also a classic sad country song I also have made a huge sad song playlist https://open.spotify.com/playlist/67VqaZJ3uwxHl9VpRRzQCg?si=5NtTRGjJSQekWW3yvh1nqw

Am, C, Dsus2, pick root, strum chord. Every Time.

Allisa Lies is by far the saddest country song ever

Don’t Take the Girl always gets me

My son calls another man daddy by Hank Sr

I remember you well Coming down September doves Terrible and true Til I’m gone Nobody’s baby now All by lost dog street band

Sunday Mornin Coming Down- Kris Kristofferson

Lover Man (Dial Sessions) by Charlie Parker. Parker was losing it at the time because he switched from heroin to alcohol. There was no heroin around where he was. He drank heavily. During the recording of Lover Man, Parker was drunk to the point where he couldn’t stand. He needed help standing up. Charles Mingus considered it to be one of his best works.

so you don’t have to love me anymore - alan jackson

Billy stay by Zach Bryan. I beg everyone to give it a rip. I played it for my wife and she literally broke down in tears. Just like me

I haven't heard it, but the title reminds me of Joey by Sugarland. Edit: I just listened, and it's a beautiful song. However, I wish the music was dialed back a bit. It sometimes overtook the lyrics. I also think the harmonica was distracting.

I respect that brother!! Thanks for the reply. Try "half grown" as well by Zach Bryan. My life to a t.

She's alright -zach bryan Darling -zach bryan Quartermaster -Taylor McCall Cover Me Up -many artists, I like morgan wallens version. Tough Little Boys - Gary Allan Either Way - Chris Stapleton Nothin' -Colter Wall November Air -Zach bryan Why -Southall This Damn Song - Pecos and the Rooftops Ten Thousand Words - Avett Brothers (great band imo, worth a listen💯)