Every love story that doesn’t have a happy ending inevitably leads to heartbreak for someone. Perhaps no other genre captures the emotions of a breakup better than country music. That’s why we decided to put together a playlist of country breakup songs.
The honest, heartfelt lyrics often deal with painful truths addressing what went wrong in a relationship and how the ex-lovers are getting on with their lives after the breakup. Whether you are experiencing heartbreak at the moment or just want to feel a little nostalgia for a past relationship, this collection of songs is sure to bring out all of the emotions. We also have a playlist of sad breakup songs from across all music genres if you’re interested.
Table of Contents
1. Trouble With A Heartbreak by Jason Aldean
“Trouble With A Heartbreak” was recorded by Jason Aldean and released on his 2022 album Macon, Georgia. The song left a big impression on Jason Aldean the first time he heard it. Songwriters Brett Beavers, John Morgan, Kurt Allison, and Tully Kennedy combined classic country sounds with hints of R&B on this tune about dealing with a breakup that left the narrator heartbroken. The song topped the Billboard Country Airplay chart and showcases Aldean’s more sensitive side. The lyrics indicate that no matter what he tries two do to get over his heartbreak, nothing other than time will help heal his wounds.
2. What Hurts the Most by Rascal Flatts
|Album||Me and My Gang|
Originally written by songwriters Jeffrey Steele and Steve Robson, “What Hurts the Most” was later covered by Rascal Flatts and released on their 2006 album Me and My Gang. Their version was wildly successful, topping the Billboard Hot Country Songs chart and the Billboard Adult Contemporary chart. The song was later certified 5x Multi-Platinum by the RIAA. Rascal Flatts performed “What Hurts the Most” with Kelly Clarkson at the 2006 Academy of Country Music Awards. The following year, the recording was nominated for Best Country Song and Best Country Performance by a Duo or Group with Vocals at the 49th Annual Grammy Awards. The music video currently has over 177 million views on YouTube.
3. You’ll Think of Me by Keith Urban
“You’ll Think of Me” was co-written by Darrell Brown, Dennis Matkosky, and Ty Lacy. It was recorded by Australian country-pop singer Keith Urban and released on his 2004 album Golden Road. The song topped the Billboard Hot Country Songs chart and was a top 10 hit on the Adult Contemporary chart and the Adult Top 40 chart. In addition to the song being certified 2x Multi-Platinum by the Recording Industry Association of America, it would go on to become Keith Urban’s first Grammy Award in the Best Male Country Vocal Performance category at the 2006 ceremony.
4. Break Up In The End by Cole Swindell
|Album||All of It|
Originally pitched to Luke Bryan and Dan + Shay, “Break Up In The End” was recorded by Cole Swindell and released on his 2018 album All of It. Swindell decided to record the song because he related to its central theme of staying in a relationship even though he knew that it would not work out in the end. Co-songwriter Jessie Jo Dillon noted that the title was inspired by the book John Dies at the End, where the ending is given away and carried that idea into the lyrics of the song. Despite the heartbreak, Swindell sings that he’s happy to have experienced the relationship.
5. Before He Cheats by Carrie Underwood
We’ve all heard about someone’s crazy ex-girlfriend or ex-boyfriend, but the woman in Carrie Underwood’s song “Before He Cheats” may take the cake for being the craziest. The lyrics tell the story of a bitter breakup and detail a woman exacting revenge on her lying, cheating ex-lover. The song was co-written by Nashville songwriters Josh Kear and Chris Tompkins. “Before He Cheats” was a massive commercial success and was a top ten hit on five separate Billboard charts. It was certified 7x Multi-Platinum and won Underwood and the songwriters numerous awards.
6. Miss Me More by Kelsea Ballerini
“Miss Me More” is a country-pop song recorded by Kelsea Ballerini and was released as the third single on her 2017 album Unapologetically. The breakup song recounts the various aspects of her personality that Ballerini sacrificed to please her former lover. Ballerini laments that she thought she would miss her ex but ended up realizing that she misses her former self more. “Miss Me More” peaked at #2 and #7 on the Billboard Country Airplay and Hot Country Songs charts, respectively, and was later certified 2x Multi-Platinum by the RIAA.
7. Break Up In A Small Town by Sam Hunt
“Break Up In A Small Town” was inspired by Sam Hunt’s tumultuous relationship with his wife, Hannah Lee Fowler. The pair have had an up-and-down affair, with Fowler filing for divorce from Hunt, accusing the singer of adultery and improper treatment of a spouse. Hunt’s wife later requested the court to dismiss her divorce filing, and it has been reported that the couple has reconciled their relationship. The song peaked at number 2 on both the Billboard Country Airplay and Hot Country Songs charts. “Break Up In A Small Town” was also a big commercial success, later being certified 5x Multi-Platinum by the RIAA.
8. Like We Never Loved At All by Faith Hill (Featuring Tim McGraw)
|Genre||Country, Country Pop|
“Like We Never Loved At All” tells the story of a couple whose love has started to drift away. To one another, their ex-lover appears to be doing fine after the breakup and getting on with their life, while they struggle to move on. The song was written by John Rich of the country group Big & Rich, along with Vicky McGehee and Scot Sax. It was recorded by Faith Hill and her husband Tim McGraw. The song would go on to peak at #5 on the Billboard Hot Country Songs chart and won a Grammy Award for Faith Hill and Tim McGraw in the Best Country Collaboration with Vocals category at the Grammy Awards in 2006.
9. Tequila by Dan and Shay
|Album||Dan + Shay|
“Tequila” is a popular breakup song about a man whose memories of his ex-girlfriend come pouring back in whenever he drinks tequila. It was co-written by Dan Smyers, Nicolle Galyon, and Jordan Reynolds. The song was a huge commercial success, topping both the Billboard Country Airplay and Hot Country Songs charts. In January 2022, the song was certified 7x Multi-Platinum by the RIAA. The music video, directed by Patrick Tracy, features actor and deaf activist Nyle DiMarco and has over 144 million views on YouTube.
10. I Will Always Love You by Dolly Parton
Written and recorded by Dolly Parton, “I Will Always Love You” is one of the most famous breakup songs of all time. Interestingly though, the song isn’t actually about a romantic relationship but rather a farewell dedicated to her business partner and mentor, Porter Wagoner, when Parton decided to pursue a solo career. The song was a commercial success for Dolly, topping the Billboard Hot Country Songs chart twice, in 1974 and again in 1982. But the most popular recording by far is the soulful version sung by Whitney Houston for the film The Bodyguard, which was certified Diamond by the RIAA.
11. Let It Rain by David Nail (Featuring Sarah Buxton)
|Album||The Sound of a Million Dreams|
“Let It Rain” is a breakup song co-written by David Nail and Jonathan Singleton. It was released as the lead single off of David Nail’s 2011 album, The Sound of a Million Dreams. It would go on to become Nail’s first number-one single, topping Billboard’s Hot Country Songs chart, and has been certified Gold by the RIAA. Co-writer Jonathan Singleton has mentioned that the song was partially inspired by the romantic comedy film, The Last Kiss. The lyrics detail a man’s remorseful state after cheating on his girlfriend. He knows he messed up and is accepting whatever karmic retribution comes his way, including losing his partner forever. This is one of my personal favorite songs about regret and the consequences of huge mistakes. It’s also a powerful song about rain, so to speak, that very effectively uses metaphors to make the song even more powerful.
12. What If I Never Get Over You by Lady Antebellum
Written primarily by singer-songwriter Ryan Hurd, the lyrics to “What If I Never Got Over You” were meant to capture the constant, never-ending heartbreak Hurd imagined he would feel if he were to separate from his wife, country singer Maren Morris. Lady Antebellum recorded the song and released it as the lead single on their 2019 album Ocean. The song topped the Billboard Country Airplay chart and was certified Platinum by the RIAA. Lady Antebellum performed “What If I Never Got Over You” at the 53rd Annual Country Music Association Awards with Halsey. If you’re looking for sad country breakup songs, then this is certainly one you’ll want to have on your playlist.
13. You Don’t Know Her Like I Do by Brantley Gilbert
|Album||Halfway to Heaven|
“You Don’t Know Her Like I Do” was co-written by Brantley Gilbert and Jim McCormick. It was recorded by Gilbert and released on his 2011 album Halfway to Heaven. The song was a huge commercial success and earned Brantley Gilbert a certified Platinum record. It topped the Billboard Hot Country Songs chart and ended up being the second-most-played song on country radio in 2012. The lyrics depict a phone call between a friend checking in with another friend. A man that is not quite ready to say goodbye to his now ex-girlfriend.
14. Mama’s Broken Heart by Miranda Lambert
|Album||Four the Record|
“Mama’s Broken Heart” was co-written by Kacey Musgraves, Brandy Clark, and Shane McAnally. It was recorded by Miranda Lambert and released as the fourth single on her 2011 album Four the Record. The lyrics detail the story of a woman having a hard time dealing with a breakup. The people in her town start gossiping about her because she isn’t handling the split from her boo with grace, or being very “ladylike.” Lambert laments that, unlike her mama’s generation, that would have simply accepted the breakup and pretended to be okay to save face, she sacrificed her reputation to exact revenge on her ex.
15. Break Up With Him by Old Dominion
|Album||Meat and Candy|
“Break Up with Him” was written and recorded by Nashville-based country group Old Dominion. The song became the band’s first #1 country hit, topping the Billboard Country Airplay chart. It was later certified Platinum by the RIAA. The lyrics tell the story of a man in love with a woman that is still in a relationship. He encourages her to breakup with her current lover so they can finally be together. The official music video, which has over 51 million views on YouTube, references the 1985 film Back to the Future, with lead singer Matthew Ramsey portrayed as Marty McFly.
16. Keep It To Yourself by Kacey Musgraves
|Album||Same Trailer Different Park|
“Keep It To Yourself” was co-written by Kacey Musgraves along with renowned songwriters Shane McAnally and Luke Laird. The lyrics tell the story of a woman trying to get over her ex and not wanting to know how they are feeling because she doesn’t want to go back to that relationship. The song was released as the last single on Musgraves’ 2014 album Same Trailer Different Park. Musgraves reminds listeners that sometimes the best way to get over a breakup is to simply be left alone so that you may heal. If you resonate with this song, check out our playlist of songs about being alone here.
17. Over When It’s Over by Eric Church
“Over When It’s Over” was co-written by Eric Church and chart-topping songwriter Luke Laird, who has written over twenty Billboard #1 singles. The song was released on Church’s award-winning 2011 album, Chief, which was named by Rolling Stone magazine as one of the 500 Greatest Albums of All Time. The lyrics of the song recount the final resolution of a relationship, noting that no matter what the ex-lovers try to do, they will never get the magic back. The song is a fan-favorite at Eric Church concerts, and the live music video for the song was recorded at Chattanooga’s Tivoli Theatre and released on Church’s first live album, Caught In The Act: Live.
18. Crazy by Patsy Cline (Featuring the Jordanaires)
“Crazy” is a country breakup song written by Willie Nelson and popularized by Patsy Cline. The song was featured on Cline’s 1961 album Showcase. Nelson allegedly wrote the song in less than an hour, while he was driving from his home in Pasadena, Texas, to nearby Houston. The song has been covered by many artists, from Linda Ronstadt to LeAnn Rimes. In 2003, the Library of Congress inducted Cline’s version of “Crazy” into the National Recording Registry.
19. Bye, Bye by Jo Dee Messina
“Bye, Bye” was recorded by Jo Dee Messina and released on her 1998 album I’m Alright. It was co-written by Rory Bourke and Phil Vassar. The song spent two non-consecutive weeks on the Billboard Hot Country Songs chart. The lyrics are empowering as Messina sings that she is not going to sit around and wait for or get back together with her former lover who she thought could have been her Mr. Right. The music video for the song, which has nearly ten million views on YouTube, was nominated for the Country Music Association Award for Video of the Year.
20. Mercy by Brett Young
“Mercy” is a powerful breakup song co-written by Brett Young and Sean McConnell. It was recorded by Young and released on his 2017 self-titled debut album. McConnell has written other hit songs for famous country musicians such as Tim McGraw, Brad Paisley, and Martina McBride. The song has enjoyed tremendous success, becoming a #1 hit on the Billboard Country Airplay chart, and has been certified 4x Multi-Platinum by the Recording Industry Association of America. The music video currently has over 233 million views on YouTube.
21. Brokenheartsville by Joe Nichols
|Album||Man with a Memory|
“Brokenheartsville” is a classic country breakup song recorded by Joe Nichols and released on his 2002 albums Man with a Memory. The lyrics tell the story of a man whose woman left him for another lover. He compares his ex’s new boyfriend to the devil and is caught drinking his heartache away as a means to help him move on from the relationship. “Brokenheartsville” became Joe Nichols’ first #1 hit on the Billboard Hot Country Songs chart. The song was nominated for a Grammy for Best Male Country Vocal Performance but lost to Vince Gill’s song “Next Big Thing.”
22. Drinkin’ Me Lonely by Chris Young
“Drinkin’ Me Lonely” is a breakup song about a man drowning the sorrows of his failed relationship at a bar. He laments that while he is trying to drink his blues away, the heartache is too strong, and he is still left feeling lonely. It was co-written by Chris Young and Larry Wayne Clark and released as Young’s debut single shortly after he won season four of Nashville Star. The song peaked at #42 on the Billboard Hot Country Songs chart. It was featured on Young’s only album not to feature a Top 40 single.
23. Die From A Broken Heart by Maddie & Tae
|Album||The Way It Feels|
“Die From A Broken Heart” was co-written by Maddie Marlow and Taylor Dye, together with songwriters Deric Ruttan and Jonathan Singleton. The song details the emotional phone call from a daughter to her mother, whom she seeks comfort and advice following a painful breakup. The heartache feels so intense she innocently asks if she can die from a broken heart. The song was certified 2x Multi-Platinum on July 14, 2022, by the RIAA. The music video has over 76 million views on YouTube as well, which is extremely impressive.
24. Just To See You Smile by Tim McGraw
“Just to See You Smile” spent six weeks atop the Billboard Hot Country Singles & Tracks chart and a total of 42 weeks on the chart, setting a record at the time for being the longest-running single on the Billboard chart. The song was co-written by hit record-making songwriter Tony Martin and Mark Nesler. Many years after its release, it was certified 2x Multi-Platinum in August 2022 by the RIAA. The lyrics detail the bittersweet emotions the narrator feels for his ex-lover. He loved and still loves her so much that he would do anything to make her happy.
25. Picture To Burn by Taylor Swift
“Picture to Burn” was co-written by the queen of country breakup songs, Taylor Swift, and her longtime songwriting partner Liz Rose. The song was released as the fourth single on Swift’s 2006 self-titled debut album. It peaked at #3 on the Billboard Hot Country Songs chart and was certified 2x Multi-Platinum by the RIAA. The lyrics tell the story of a breakup the narrator is working through. She obviously still has some feelings for her ex-boyfriend but is leaning into her anger with him for leaving her for someone new. The music video, which is complete with fiery pyrotechnics, has over 114 million views on YouTube. This is one of the most popular angry breakup songs of all time, with the music video on YouTube racking up 100s of millions of views.
26. Blame It On Your Heart by Patty Loveless
|Album||Only What I Feel|
“Blame It on Your Heart” was co-written by Harlan Howard and Kostas. It was recorded by Patty Loveless and released on her 1993 album Only What I Feel. The lyrics describe the narrator’s no-good, cheating ex-boyfriend and imply that any heartache or bad luck that comes his way is the fault of his own wicked ways. The song spent a week atop the Billboard Hot Country Songs chart. The song was performed by River Phoenix in the 1993 film The Thing Called Love. Cheating is one of the worst things anyone can do. If you’ve recently been cheated out, head over to our songs about betrayal playlist because you’ll probably relate to many of them.
27. Damn Strait by Scotty McCreery
“Damn Strait” is not your typical country breakup song. The lyrics pay homage to one of Scotty McCreery’s musical heroes, George Strait. He claims he cannot listen to any of his old favorite George Strait songs because it brings back painful memories of good times with his ex-lover. It was written by Jim Collins and Trent Tomlinson, recorded by Scotty McCreery, and released on his 2021 album Same Truck. Overall, the song speaks of the indelible impact music can have on our emotions when we associate certain songs with a particular time or person in our lives. In my opinion, this is a massively underrated song.
28. Wish I Didn’t Know Now by Toby Keith
“Wish I Didn’t Know Now” is a relatable breakup song to anyone who has ever found out something about their lover that made it impossible for them to stay in the relationship. The song peaked at #2 on the Billboard Hot Country Songs chart and spent over twenty weeks on the chart. It was written by Harold Shedd and Nelson Larkin. The title of the song and main lyrical hook was inspired by a line in the Bob Seger song “Against the Wind.”
29. A Better Man by Clint Black
“A Better Man” was co-written by Clint Black and Hayden Nicholas. It is about as positive of a breakup song as one can get, with the narrator looking back on his past relationship fondly and attributing his ex to helping make him a better man. The song topped the Billboard Hot Country Songs chart, finished #1 on the year-end chart, and was a big reason for Black winning the Country Music Association’s Horizon Award in 1989.
30. More Than A Memory by Garth Brooks
|Album||The Ultimate Hits|
“More Than A Memory” was co-written by Lee Brice, Kyle Jacobs, and Billy Montana. It was recorded by Garth Brooks and released on his third compilation album, The Ultimate Hits. The song set a record for the highest-debuting single on the Billboard Hot Country Songs chart, improbably debuting at #1 on the chart. The lyrics recount a man’s attempt to forget about his ex-lover by burning anything that reminded him of her and drowning the memories of her in alcohol. But despite his efforts, he can’t get her out of his mind. Thus, he laments, she is “more than a memory.”
31. You Were Mine by The Chicks
|Album||Wide Open Spaces|
“You Were Mine” is a melancholy breakup song co-written by the Erwin sisters, now with the married names Emily Strayer and Martie Maguire of the band formerly known as the Dixie Chicks. The song topped the Billboard Hot Country Songs chart. “You Were Mine” was instrumental in bringing the Dixie Chicks together and helped form the band into the chart-topping, award-winning group they were destined to become. Producer Lloyd Maines recommended the Erwin sisters invite his daughter Natalie to sing lead vocals on a demo recording of the song instead of their then-current lead singer Laura Lynch. They took him up on the recommendation, Natalie returned to her home of Lubbock, Texas, to cut the demo, and the rest, as they say, is history.
32. What He Didn’t Do by Carly Pearce
|Album||29: Written in Stone|
“What He Didn’t Do” is a hopeful breakup song written by Carly Pearce alongside Ashley Gorley and Emily Shackleton. They wrote the song in late 2020, after the divorce from Pearce’s then-husband Michael Ray. It was recorded by Pearce and released on her 2022 album 29: Written in Stone. Unlike many breakup songs that name all of the things an ex-lover did wrong that led to the relationship ending, the lyrics in Pearce’s song list all of the things he didn’t do to keep their love alive. In just over a month on YouTube, the music video has racked up over 1.5 million views.
33. The One That Got Away by Jake Owen
|Album||Barefoot Blue Jean Night|
“The One That Got Away” was co-written by Jake Owen, along with Jimmy Ritchey and Dallas Davidson. It was recorded by Owen and released on his 2012 album Barefoot Blue Jean Night. The idea for the song came when Owen was reminiscing about a former lover he had from when he was a teenager. He reflected positively on the relationship, although it was a summer fling and ultimately had an expiration date, thus presenting him with “the one that got away.” The song was a commercial success for Owen and topped the Billboard Country Airplay chart. We all have someone who got away in the past. If you resonate with this song, check out our playlist of songs about second chances because many of them are relatable to this song.
34. Wasting All These Tears by Cassadee Pope
|Album||Frame by Frame|
“Wasting All These Tears” is a country pop song co-written by singer-songwriters Caitlyn Smith and Rollie Gaalswyk. It was recorded by Cassadee Pope and released on her 2013 album Frame by Frame. The song would earn Pope her first Gold record and would later become certified Platinum by the RIAA. “Wasting All These Tears” was a Top 10 hit on both the Billboard Hot Country Songs and Country Airplay charts. The music video for the song was directed by Brian Lazzaro and won Breakthrough Video of the Year at the 2014 CMT Music Awards.
35. Whiskey Sour by Kane Brown
“Whiskey Sour” was co-written by Adam Craig, Jaxson Free, and Josh Hoge. It was recorded by up-and-coming country star Kane Brown and released on his 2022 album Different Man. The lyrics depict a man that is left heartbroken and lost following his recent breakup with the woman he thought would be his wife. He does what he can to try and forget his ex, including drinking, but even his favorite drink reminds him of her. The official music video has nearly five million views in just ten months on YouTube and has amassed over fifteen million streams on Spotify.
36. Always On My Mind by Willie Nelson
|Album||Always On My Mind|
“Always On My Mind” was originally recorded by Gwen McCrae in 1972 and first released by Brenda Lee later the same year. Just four months after Lee’s version was released, the King of Rock and Roll, Elvis Presley, released his own rendition of the tune, which would become a smash hit. But it is the sincere and heartfelt cover by Willie Nelson that has become the standard version of the song. Nelson’s acclaimed version won multiple Grammy Awards and CMA awards, was certified Platinum, and in 2008, “Always On My Mind” was inducted into the Grammy Hall of Fame.
37. If You See Him, If You See Her by Reba McEntire and Brooks & Dunn
|Album||If You See Him|
“If You See Him, If You See Her” is a duet recorded by country powerhouses Reba McEntire and Brooks & Dunn. It was written by Terry McBride, Tommy Lee James, and Jennifer Kimball. The song was released on the same day by both McEntire and Brooks & Dunn on their respective albums If You See Him and If You See Her. The song recounts the longing one feels for their ex-lover even after the fire has burned out, and they have both moved on. The tune spent two consecutive weeks atop the Billboard Hot Country Songs chart. The music video also has nearly fifteen million views on YouTube.
38. Here’s A Quarter (Call Someone Who Cares) by Travis Tritt
|Album||It’s All About to Change|
“Here’s A Quarter (Call Someone Who Cares)” is a song written and recorded by Travis Tritt. It was released as the lead single on his 1991 album It’s All About to Change. The lyrics recount a relationship where the man was caught off guard when his partner left him alone, only to come back, trying to rekindle their romance. Tritt offers her a quarter, as there were still payphones around when the song was released and tells his ex to call someone who cares. The song was a fan favorite, and Travis Tritt would have to be careful when playing it at concerts as members of the audience would rain quarters down on the stage. If you like this song, check out our playlist of songs about letting go.
39. Every Light in the House by Trace Adkins
|Album||Dreamin’ Out Loud|
“Every Light in the House” was written by songwriter Kent Robbins. He wrote it one year before he died in a car accident. Robbins was posthumously inducted into the Nashville Songwriters Hall of Fame. The song was recorded by Trace Adkins and released on his 1996 album Dreamin’ Out Loud. “Every Light in the House” peaked at #3 on the Billboard Hot Country Songs chart, giving Adkins his first Top 5 hit. The lyrics recount the ever-lasting love a man has for his now ex-lover. He tells her that he respects her decision to end the relationship but assures her that if she ever changes her mind, he will leave a light on in his heart for her to return.
40. Break Down Here by Julie Roberts
“Break Down Here” was co-written by Jess Brown and Patrick Jason Matthews. It was recorded by Julie Roberts and released as the lead single off her 2004 self-titled album. The song peaked at number 18 on the Billboard Hot Country Songs chart. Even more impressive, though, Julie Roberts debuted at #1 on the Billboard Hot Country Singles Sales, making her the first solo female artist to enter the chart at the top position since LeAnn Rimes opened at #1 with “I Need You” in 2000. The lyrics are about a woman that left her troubled relationship and is hoping that nothing else goes wrong as she is leaving town and her man behind.
41. Misery and Gin by Merle Haggard
|Album||Back to the Barrooms|
“Misery and Gin” was co-written by Snuff Garrett and John Durrill for the Clint Eastwood film Bronco Billy. It was recorded by Merle Haggard and released both on the Bronco Billy soundtrack as well as Haggard’s 31st studio album, Back to the Barrooms. A common theme in country breakup songs, the narrator of the tune, seems to always find himself at a bar trying to drown his memories, only to have those memories come back even stronger and continue to haunt him. The song was the third most-played song on country radio in 1980.
42. Watching Airplanes by Gary Allan
“Watching Airplanes” was written by Jim Beavers and Jonathan Singleton. It was recorded by Gary Allan and released on his 2007 album Living Hard. Peaking at #2 on the Billboard Hot Country Songs chart, it became Allan’s tenth Top 10 hit. The song was partly inspired by Allan’s late wife, a flight attendant who committed suicide three years earlier. The lyrics are open to interpretation, though, and seem to imply that the narrator’s relationship has ended because he didn’t give it enough effort or attention. “Watching Airplanes” was nominated for Single Record of the Year at the 43rd Annual Academy of Country Music Awards but lost out to Sugarland’s “Stay.”
43. Neon Moon by Brooks & Dunn
|Album||Brand New Man|
“Neon Moon” is a classic country breakup song written by Ronnie Dunn. It was recorded by his band Brooks & Dunn and released on their 1992 album Brand New Man. The lyrics offer a hideaway bar as a place of refuge for those reeling with a broken heart from losing their loved one. The song features the haunting sound of a steel guitar, which perfectly complements the melancholy lyrics of someone down on their luck, pining over their ex. “Neon Moon” became Brooks & Dunn’s third consecutive #1 single on the Billboard Hot Country Songs chart.
44. I’m Gonna Miss Her (The Fishin’ Song) by Brad Paisley
“I’m Gonna Miss Her (The Fishin’ Song) was co-written by Brad Paisley and longtime friend, songwriter, and producer Frank Rogers. The two friends met in Nashville while attending Belmont University. Paisley recorded the song and released it on his 2002 album Part II. It would go on to become his third #1 single, topping the Billboard Hot Country Songs chart for two weeks. It also earned Paisley a Gold record. The lyrics tell the story of a woman fed up with her partner, who she thinks spends too much time fishing. The narrator admits that he will likely miss his girl if she leaves but decides to go fishing anyways. The music video features clips of ESPN commentator Dan Patrick and also talk show host Jerry Springer. If this song hit you, check out our playlist of songs about missing someone.
45. For the Good Times by Ray Price
|Album||For the Good Times|
“For the Good Times” was written by legendary singer-songwriter Kris Kristofferson and originally recorded by Bill Nash in 1968. Kristofferson recorded the song himself and released it in 1970 on his own debut studio album. Just months later, Ray Price recorded and released his chart-topping version of the song, making it a breakthrough hit for the songwriter. The tune won “Song of the Year” and “Single of the Year” at the 1971 Academy of Country Music Awards. In 2014, Rolling Stone named “For the Good Times” #18 on its list of the 40 Saddest Country Songs of All Time. Contemporary country star Kacey Musgraves considers it the saddest song of all time, noting that listening to it really breaks her heart.
46. Help Me Make It Through the Night by Sammi Smith
|Album||Help Me Make It Through the Night|
“Help Me Make It Through the Night” is a country breakup ballad written and originally recorded by Kris Kristofferson. The song became a crossover hit when Sammi Smith released her chart-topping cover shortly after Kristofferson’s own recording was released. Smith’s version has been covered by dozens of esteemed artists through the years and became a #1 single on the Billboard Hot Country Songs chart. Smith won the Grammy Award for Best Female Country Vocal Performance at the 14th Annual Grammy Awards in 1972.
47. Sticks and Stones by Tracy Lawrence
|Album||Sticks and Stones|
“Sticks and Stones” was co-written by Elbert West and Roger Dillon. It was recorded by Tracy Lawrence and released on his 1991 debut studio album of the same name. Just before the release of his album, Lawrence and his then-girlfriend were mugged by several gunmen. In an effort to save his girlfriend and allow her to flee, Lawrence fought back but was shot four times. Thankfully, Lawrence had a speedy recovery, and all the publicity that came with being in the news from the attack helped propel “Sticks and Stones” to #1 on the Billboard Hot Country Songs chart.
48. Better Class of Losers by Randy Travis
“Better Class of Losers” was co-written by Randy Travis and Alan Jackson. The song peaked at #2 on the Billboard Hot Country Songs chart and earned Travis a nomination for Best Male Country Vocal Performance at the 35th Annual Grammy Awards. The lyrics tell the story of a man who is unhappy in his relationship with a high-society woman. He yearns for a simpler life, with friends that are more down-to-earth, or as he jokingly calls them, a better class of losers. This is easily one of the best country breakup songs of all time.
49. Drunk On A Plane by Dierks Bentley
“Drunk On A Plane” is a comical breakup song that details how a man deals with his fiance leaving him on their wedding day. Despite the shock and sorrow of being essentially left at the alter, he decides to go on the couple’s honeymoon trip solo and tries to make the most of his situation. Co-written by Dierks Bentley, Chris Tompkins, and Josh Kear, the song was recorded by Bentley and released on his 2014 album Riser. The song charted at #1 and #3 on the Billboard Country Airplay and Hot Country Songs charts, respectively. It would go on to become certified 3x Multi-Platinum by the RIAA.
50. She Let Herself Go by George Strait
|Album||Somewhere Down in Texas|
“She Let Herself Go” is a breakup song about a woman that goes on to live a life full of adventure after she separates from her former lover. The title and hook of the song are a clever play on words as the traditional expression of letting oneself go implies that they are giving up on trying or begin to look disheveled in a sense. But the lyrics flip this around and instead use it as a way of saying the woman let go of her inhibitions or self-placed limitations to live her life to the fullest. The song became George Strait’s 40th #1 single on the Billboard Hot Country Songs chart and earned him a Gold record from the RIAA.
51. When It Rains It Pours by Luke Combs
|Album||This One’s For You|
“When It Rains It Pours” is a song co-written and recorded by Luke Combs for his 2017 album, This One’s For You. The song is about Luke Combs’ girlfriend that left him because she was fed up with him partying too much with his friends. Unlike many breakup songs that focus mainly on the sad emotions after a relationship ends, Combs sings about all of the good luck that came his way after she left him. The song topped both the Billboard Hot Country Songs and Country Airplay charts and has been certified 4x Multi-Platinum by the RIAA.
52. Red Light by David Nail
|Album||I’m About to Come Alive|
“Red Light” was recorded by David Nail and released on his 2009 album I’m About to Come Alive. The lyrics tell the story of a man that was enjoying a drive with his lover on a beautiful day, only to be blindsided by her breaking up with him while they were stopped at a red light. The song captures the surprise some people feel when their significant other decides to break up with them seemingly out of nowhere. “Red Light” was Nail’s highest-charting song, peaking at #7 on the Billboard Hot Country Songs chart, until his “Let It Rain” topped the chart three years later.
53. Picture by Kid Rock (Featuring Sheryl Crow or Allison Moorer)
“Picture” is a breakup duet song originally written and recorded by Kid Rock and Sheryl Crow. When Kid Rock’s record label, Atlantic Records, was not able to get permission from Crow’s label to release the song as a single, Atlantic brought in Allison Moorer to re-record Crow’s vocals for the promotional release. Despite this issue, some radio stations decided to play the original version. Thus, when the song began climbing the charts, Billboard credited the song to Kid Rock featuring Sheryl Crow or Allison Moorer.
54. Goodbye Earl by Dixie Chicks
“Goodbye Earl” is one of the wilder country breakup songs out there. It was written by songwriter Dennis Linde, who is best known for writing the Elvis Presley hit “Burning Love.” The rockin’ murder ballad details the story of a woman who is the victim of her abusive husband. Her friends learn of her dire situation and decide to take matters into their own hands, killing ‘Earl’ before he can hurt their friend again. The music video for “Goodbye Earl” won the Video of the Year Awards at both the CMA and ACM Awards.
55. Cold by Chris Stapleton
“Cold” was co-written by Chris Stapleton and released as the third single on his 2020 album Starting Over. He performed the song live at the 55th Annual CMA Awards and also the following year at the 64th Annual Grammy Awards, where “Cold” earned Stapleton a Grammy Award for Best Country Song. The song topped the Billboard Bubbling Under Hot 100 Singles and earned Stapleton a Gold record. The lyrics detail the account of a man that feels blindsided by the breakup with his then-girlfriend. He wonders how he will go on living his life without her and repeatedly asks why she had to be so cold as to do this to him when he thought everything between them was good.
56. Tim McGraw by Taylor Swift
“Tim McGaw” was co-written by Taylor Swift and songwriter Liz Rose. It was featured on Swift’s 2006 self-titled debut album. The lyrics recount a summer romance that has come to an end, but the bittersweet memories remain. The narrator hopes that her summer fling remembers her and feels nostalgia every time he hears a song from her favorite artist, legendary country singer Tim McGraw. The song peaked at number 6 on the Billboard Hot Country Songs chart and was later certified 2x Multi-Platinum by the RIAA.
57. I Hope You’re Happy Now by Carly Pearce (Featuring Lee Brice)
“I Hope You’re Happy Now” is a classic country duet recorded by Carly Pearce and Lee Brice. It was co-written by Pearce alongside Luke Combs, Randy Montana, and Jonathan Singleton. Luke Combs was originally slated to sing on the track with Pearce but decided to step down as he had his own album out at the time and wanted Pearce’s song to have the most exposure possible. Although he was busy out on the road, Brice recorded his part remotely and sent his vocals digitally. The song finds Pearce apologizing for her part in the relationship not working out. Ultimately, both parties agree to end on good terms and wish each other well.
We hope things songs helped at least a little during your difficult time. If there are any songs that you feel we should add to this list, let us know in the comments section below.
Hi, my name is Kevin and I’m from Butler, Pennsylvania. I’ve been obsessed with music and audio gear for as long as I can remember. I started this website to help people find professional advice related to a wide range of audio topics. We have a number of Audio Engineers on our team who have been designing and fixing audio gear for decades.