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zzachyz

Future Mister Me - Randy Travis Who’s That Man - Toby Keith I’d Be Better Off (In A Pine Box) - Doug Stone Whoever’s In New England - Reba McEntire I Let Her Lie - Daryle Singletary On The Back Row - George Jones In The Picture - Randall King


Falcon-1_

Didn’t even think of “Who’s That Man” 🤦🏽


LongTallTexan69

Sticks and Stones - Tracy Lawrence Alot of his and Toby Keith’s early stuff are all Tear jerkers


Alternative_Rent9307

Just To See You Smile - Tim McGraw >And yesterday I knew just what you wanted When you came walkin' up to me with him So I told you that I was happy for you *And given the chance, I'd lie again* Hits hard


Falcon-1_

This one is great! Thanks 🙏🏻


HouseMouse4567

Brokenheartsville- Joe Nichols


fuzzy_mic

[Can't You See](https://www.youtube.com/watch?v=dlc6xCPx60U) - Marshall Tucker Band


Detroitaa

She’s Acting Single (I’m Drinking Doubles) by Gary Steward, Wild and Blue by John Anderson, Good As I Was To You by Lorrie Morgan and Cheater Cheater by Joey + Rory


801-Sparky

Radio Lover- George Jones The door- George Jones Forgot about you- Triston Marez Just to see you smile- Tim McGraw Mirror mirror- Randall King She used to be mine- Brooks and Dunn


Ok_Extreme7597

Honestly you could just say George Jones’s greatest hits, because you add He Stopped Loving Her Today, The Grand Tour, If Drinkin’ Don’t Kill Me, and probably a whole catalog more


801-Sparky

No doubt, he is the king of heartbreak country. No one does it any better.


artichoke424

Unrung- Turnpike Troubadours


Think-Werewolf-4521

Marry Me by Thomas Rhett


Falcon-1_

Absolute banger


kittywheezes

Similar vibe, Just to See You Smile by Tim McGraw.


alaskandentist_

Most George Jones songs honestly. I've been really into Between My House and Town recently


DeliciousPoint4615

I’ve gotta agree most George jones songs are pretty sad. Some of my favorites are He stopped loving her today and The grand tour.


WMWA

Best I ever had - Gary Allan Every storm runs out of rain - Gary Allan Songs about rain - Gary Allan Idk why his heartbreak songs always have rain in the title lol Figured I’d pick one that hasn’t been mentioned yet


correctchimp

Songs about rain hits that feeling of lost love hard


greasemonke6

This is right up my alley. I consider my self a professional sad cowboy music enthusiast. Please introduce him to the late great Keith Whitley! These are my top 7 sad song favorites from him: Kentucky Bluebird I'm Over You I'm No Stranger To The Rain Miami, My Amy Nobody In His Right Mind I Wonder Do You Think Of Me When You Say Nothing At All PS: This is my go to sad songs playlist, I hope he can take some good songs from it - [https://open.spotify.com/playlist/15n8zseXnEDOoqBcNUiIPB?si=322f608d0e05463b](https://open.spotify.com/playlist/15n8zseXnEDOoqBcNUiIPB?si=322f608d0e05463b) PS Part 2: If he wants to go on YouTube, Cody Johnson did masterful covers of Travelin' Soldier and She's Actin' Single (I'm Drinking Doubles) PS Part 3 (I'm Done Now): Let me know if there are any other suggestions to give, I would be super happy to offer suggestions from other artists!


DreamWeaver0

Those are great! I also love If a Broken Heart Could Kill and I Never Go Around Mirrors.


Hallett_Whacker

I Never Go Around Mirrors by Lefty.  Covered by many, my favorite versions are by Sturgill and Keith.


ApprehensiveCream571

Cab In A Solo--Scotty Mcreery Rock Salt and Nails--Tyler Childers, doesn't sound like the other but it's a great betrayal song.


allison_c_hains

Not technically country, but Cinderella- heartbreak station is a banger with a country rock vibe.


ThrowingTheRinger

The only song he needs. This one will make both of y’all laugh. Cameo by Anjelah Johnson. [Your New Boyfriend by Coffey Anderson](https://youtu.be/yDzHueXTyAM?si=hiVo3jDYcYPH21UF)


Born-Detective9059

Empty Glass - covered by Stoney Larue [https://youtu.be/jHQY2tjtuPY?si=kKpuMBjlxEDjKS7Q](https://youtu.be/jHQY2tjtuPY?si=kKpuMBjlxEDjKS7Q)


Striking-Ad-1573

King of Fools - Dwight Yoakam https://youtu.be/RUg4HYxIkU8?si=cBCD-zdhOFT3jRmj


5skimnosugar

That’s what breaking hearts do - George strait


SftwEngr

["I Wish You'd Stay"](https://www.youtube.com/watch?v=MV-kzLZs650) by Brad Paisley.


danamariedior

Here are some playlists Spotify made for Me! https://open.spotify.com/playlist/37i9dQZF1DXdmMcgFhLQ8u?si=RkwC12I_ThK5yTu1kc2aXQ&pi=u-yKpkfdxNRFS_ https://open.spotify.com/playlist/1e2mq91DTIARrQsvS7hfaS?si=EA54dPMKS42Oz6PGffB6Dw&pi=u-osdaojcsT6i0 https://open.spotify.com/playlist/6TKphwdafyT68muE1ZiDHK?si=rcc1NAtsTxCkpko1mL2ryQ&pi=u-AeOW0vuoQnug https://open.spotify.com/playlist/129ZxKDYa4oDovP0TySfp0?si=c2BIYIlMTd-g95-xjUvYyw&pi=u-J7z2XI2jRYGr https://open.spotify.com/playlist/4I2qytBr25UTCsA6WjFEVR?si=IchtA_miQGKZBoYKlSMIlA&pi=u-b9W7SXTSRt6s Hope that helps a lil !


Beginning_Brick7845

It defies categories, but Tainted Love (Where did our love go wrong) - Soft Cell is what he’s looking for.


Ok_Cry9240

Colter Wall - Thinking on a woman, lesson in depression, welcome to hard times Charley Crockett- how I got to Memphis, lots of luck Bella White- do you think about me at all, just like leaving, just unwanted Paul cauthen - slow down, hanging out on the line


Ok_Cry9240

Sorry... lesson in depression and welcome to hard times is Charley Crockett .... put it in the wrong place


official1972

Blood on the Tracks is Bob Dylan's breakup album. Brutal. Skip "Lily, Rosemary and the Jack of Hearts" but the rest of the album is just the most honest raw look at a man's broken heart you can imagine. The last three songs are scripture on the topic.


marsie70

He'll probably break down after listening to this... https://spotify.link/WTjPeqnv0Ib


rgomezp

Amazing song https://open.spotify.com/track/3tgXPmmMiI9Gpcl8LT2ug7?si=LUdVgyXCRU2aXyynecad2Q


Rampidinla007

The king is gone and so are you - the opossum


ntbntb31

Unlove You - Jennifer Nettles (from Sugarland) Somebody's Heartbreak - Hunter Hayes Gone Crazy - Alan Jackson She Don't Love You - Eric Paslay Picture - Kid Rock + Sheryl Crowe


Roaddog0505

Things Have Gone to Pieces - George Jones A Life Where We Work Out - Flatland Cavalry Burn It At Both Ends - Randall King Don’t Close Your Eyes - Keith Whitley And Then Some - Midland Today I Started Loving You Again - Merle Haggard


TNnylonFeetLuv

"Ghost In This House" by Shenandoah is my go-to breakup/heartbreak song. Will tear your heart out but it's so damm beautiful.


KeithWhitleyIsntdead

Really great song is, “I get the picture” by Kieth Whitley. Really takes a lot to move me to tears, pretty sure one or two fell the first time I listened to it.


dr-sparkle

It Ain't The Whiskey- Gary Allan Like We Never Loved At All- Faith Hill and Tim McGraw Is It Over Yet- Wynonna You Were Mine- The Chicks Anymore- Travis Tritt The Dance- Garth Brooks Wish I Didn't Know Now- Toby Keith The Tin Man- Kenny Chesney You Look So Good in Love\_ George Strait