If you’ve ever suffered a heartbreak, then you know the power of music. And that’s because, when we listen to songs about heartbreak, it can be the exact medicine our soul needs to hear in order to heal.
So, in this article, I’m going to provide you with my favorite songs dealing with the topic of heartbreak. And hopefully, by the end of it, you’ll walk away with a genuine love for at least one or two of these tracks. Maybe they’ll even make it into your playlist rotation.
Where Are You Now by Janet Jackson
A lot of the time when we think about heartbreak, we think of songs that feature an artist that’s either deep in despair or outright angry at the world. But there’s a whole middle ground in between that gap, and a lot of it deals with longing, regret, and and an inability to let go of the past.
That’s kind of where we are with this Janet Jackson track Where Are You Now. On this song, you get the sense that Janet is staring out the window on a stormy night, recounting her relationship “mistakes” and finally realizing that she’s ready to love the man she let get away.
Where, where are you now
Now that I’m ready to
Ready to love you the way you
Loved me then
Where are you now
Do you still think of me
Or does your heart belong to
But, of course, the problem is that it appears her man has moved on. Janet hasn’t heard from him in a while, and the only way she gets to see his face is when she closes her eyes and hopes on a shooting star that he’ll return to her door.
If I close my eyes
And make a wish
When they open will you be right
Here with me
Where Are You Now is an excellent example of a song about heartbreak because it doesn’t shy away from the fact that, oftentimes, moving on from a breakup is a difficult and sometimes painful process.
Better in Time by Leona Lewis
On this excellent song, Leona Lewis sings of a woman that’s going through the grieving process of heartbreak. What I find interesting about this song, though, is that while Leona does indeed feel monumentally sad about being alone and no longer having her lover around, she also understands the bigger picture.
She will get over this. She will find a new love. She will be okay. The problem? Well, it’s just going to take an undetermined amount of time to finally feel “okay.”
Thought I couldn’t live without you
It’s gonna hurt when it heals too (Oh yeah)
It’ll all get better in time
And even though I really love you
I’m gonna smile ’cause I deserve to
It’ll all get better in time
Until that “time” comes where everything feels “better,” and Leona has crossed the bridge over the valley of pain and heartbreak to joy and euphoria, she’ll have to struggle through the difficulties of not being able to do simple, everyday things, like watching TV news or romantic movies that may stir up unwanted memories of her relationship that has fallen apart.
I couldn’t turn on the TV (No)
Without something there to remind me
Was it all that easy
To just put aside your feelings
And that final set of lyrics is probably what makes this song, and this topic, so tough. Because when you suffer a heartbreaking end to a loving relationship, it’s hard to know what’s ultimately worse: the fact that the relationship is over, or the fact that your lover has moved on to a new person so quickly?
Whiskey Lullaby by Brad Paisley (Featuring Alison Krauss)
The song “Whiskey Lullaby” by Braid Paisley (featuring Alison Krauss) is a prime example of a breakup song that hurt both parties. The song describes the perspective of both people in the relationship and how they both ended their lives because of the pain that they felt.
The song starts out as a man is coming home from active duty and begins with a slow and calming rhythm. The lyrics state, “She put him out, like the burning end of a midnight cigarette. She broke his heart. He spent his whole life trying to forget.” In this portion of the song, it is clear that she broke his heart and the reason becomes clear in the official music video. She cheated on him.
The song takes a depressing turn as it discusses how he was seen drinking his pain away, but still could not get her off of his mind. The lyrics then say, “He put that bottle to his head and pulled the trigger, and finally drank away her memory.”
At this point we understand that he drank himself to death over the love of this woman. The song continues, “Life is short, but this time it was bigger than the strength he had to get up off his knees.” These lyrics are repeated in a similar manner in reference to the woman further into the song.
The song has a clear metaphorical relationship between “…put the bottle” to his or her “head and pulled the trigger,” as it describes the way they each die. Instead of a gun to the head, the use the reference of a bottle, indicating they both ended their lives by drinking themselves to death. It is clear in this part of the song that the reference is aimed to help listeners understand the elongated pain of their heartbreak.
The song is about a heartbreak between two people that could not get over one another. Many heartbreaks are felt on both sides and this song touches on that point very well.
For the woman’s portion of the song, sang by Krauss, the lyrics state, “The rumors flew, but nobody knew how much she blamed herself. For years and years, she tried to hide the whiskey on her breath.” This portion of the lyrics indicate she is heartbroken and cannot get over how much she blames herself.
The lyrics then describe her method of resolution—death. Krauss sings, “She finally drank her pain away a little at a time, but she never could get drunk enough to get him off her mind until the night, she put that bottle to her head and pulled the trigger, and finally drank away his memory. Life is short but this time it was bigger than the strength she had to get up off her knees.” At this point it is indicating that she died in the same manner as him after elongated suffering from the heartbreak.
The lyrics continue, “We found her with her face down in the pillow, clinging to his picture for dear life. We laid her next to him beneath the willow, while the angels sang a whiskey lullaby.” At this point in the song we hear an angelic lullaby in the music but the lyrics, indicate a situation that was not at all peaceful. However, the end result is that the community knows their love for one another and they are buried together while the angels sing a “Whiskey Lullaby.”
This sad song reveals both sides of the heartbreak in-depth. It helps us to understand that heartbreak is not always one-sided and this is a realization to many people who assume they are the only one hurt by the heartbreak.
Overall, the song touches on heartbreak, mutual destruction and devastation, and suicide. This is a song that in undeniably one of the best heartbreak songs of all time.
Mercy by Brett Young
The song, “Mercy” by Brett Young tells the tale of an impending heartbreak that he is trying to minimize. The lyrics start out by saying, “Mercy. Why you gotta show up looking so good just to hurt me? Why you wanna stop this whole damn world from turning?”
In the beginning of the song, we realize how Young is explaining the soon-to-come heartbreak that he fears. By saying it would stop the “whole damn world from turning,” he is referring to his world—not hers. This indicates a more one-sided heartbreak, unlike the previous song.
Young continues to sing, “Mercy. Why you hanging on so tight if this ain’t working? Why you wanna stop this flame if it’s still burning? ‘Cause it’s still burnin’,” meaning that he is not completely sure how she feels about the situation. He is asking her why she is doing what she is doing, which is breaking his heart.
Young further says, “So if you’re gonna break my heart, just break it, and if you’re gonna take your shot, then take it, take it. If you made up your mind, then make it, but make this fast. If you ever loved me, have mercy.”
These lyrics drive the song home, as he asks her why she is doing this and if she can simply let him go instead of dragging out the pain of the heartbreak he knows is coming. He is asking her to show him mercy, and that comes across very clearly.
The Tracks of My Tears by The Miracles
The song “The Tracks of My Tears” by The Miracles was written by Smokey Robinson, Warren Moore, and Marv Tarplin. Tarplin had been listening to a song of Harry Belafonte’s, “The Banana Boat Song (Day-O). A combination effort went into this song, but Robinson was who wrote the song’s lyrics.
In an interview in 2006 with NPR, Robinson explained that he “finally came up with the image of tears leaving lasting marks, and the song came together.” It surely did come together, as it was covered by many artists.
The song starts off in an almost positive, upbeat way. The lyrics say, “People say I’m the life of the party ‘cause I tell a joke or two. Although I might be laughing loud and hard, deep inside I’m blue. So take a good look at my face. You’ll see my smile looks out of place. If you look closer it’s easy to trace the tracks of my tears.” This immediately jumps to the point of the song: that happiness and smiles are a way of hiding pain and heartbreak.
Un-Break My Heart by Toni Braxton
The song “Un-Break My Heart” by Toni Braxton sends shivers down your spine. The impeccable voice of Braxton shines through as she calls out for the person who damaged her heart. The chorus of the song describes a longing for this man, as her voice pulls listeners close to the emotion she feels.
The chorus of the song is the most touching, as Braxton sings with deep emotion, “Un-Break My Heart. Say you’ll love me again. Undo this hurt that you caused when you walked out the door and walked out of my life. Un-cry these tears, I’ve cried so many nights. Un-break my heart, my heart.”
The song is about a woman who is asking her partner to un-break her heart and return to her again. The song is relatable because many people feel these very emotions that are displayed in the lyrics (sadness and pain), yet they hesitate to discuss it openly, for feat that they may appear desperate or beyond repair after a breakup.
People sometimes hold onto their sad emotions during heartbreaks. But this song is a testament to the feeling of sorrows of a broken heart.
I Can’t Make You Love Me by Bonnie Raitt
The song I Can’t Make You Love Me by Bonnie Raitt is a legendary song that has also been sung by other artists, such as Teddy Swims and Sophie Millman (probably my favorite cover of this song).
This track was written by Mike Reid and Allen Shamblin. Reid told Mojo magazine that he “got the idea from a newspaper article about a guy who got drunk and shot up his girlfriend’s car. When the judge sentenced him and asked him what he had learned, the guy said, “You can’t make a woman love you if she don’t.”” This rings true for many people.
The song touches on a realization the woman has about her relationship. She understands that you cannot make someone love you, no matter how much you want it. The song is also about the understanding that a woman knows her man has lost interest, yet she wants to spend one last night with him.
What really stands out is the chorus, followed by a verse of realization. Partway into the song, Raitt sings, “Cause I can’t make you love me if you don’t. You can’t make your heart feel, something it won’t. Here in the dark, in these final hours, I will lay down my heart, and I feel the power, but you won’t. No, you won’t. Cause I can’t make you love me, if you don’t.” These very literal lyrics indicate how she accepts that he is not in love with her the way she is in love with him—and how she cannot change that fact.
The next portion after that covers another realization as Raitt sings:
I’ll close my eyes, then I won’t see
The love that you don’t feel
When you’re holding me
Morning will come and I’ll do what’s right
Just give me till then, to give up this fight
This portion of the song reads as though Raitt is telling herself how to get through this. How to get through a situation where she cannot make someone love her. She expresses how she just wants one more night before she gives up all hope.
Nothing Breaks Like A Heart by Mark Ronson (Featuring Miley Cyrus)
The song “Nothing Breaks Like A Heart” by Mark Ronson (Featuring Miley Cyrus) clearly describes how unique heartbreaks are from other types of pain.
On this track, Miley Cyrus sings, “This world can hurt you, it cuts you deep and leaves a scar. Things fall apart, but nothing breaks like a heart.” This indicates how uniquely painful a heartbreak is in comparison to other kinds of pain and disappointment. It also touches on an understanding of true heartbreak and the feelings associated with it.
Another line in the song says, “We’re broken.” This drives the theory suggested that a heartbreak breaks more than just your heart. It breaks you on deeper level.
New Rules by Dua Lipa
The song “New Rules” by Dua Lipa is set apart from the average heartbreak song because it doesn’t simply discuss the sadness, anger, or regret that may accompany a heartbreak. It addresses new rules about how to get past a breakup and move beyond a heartbreak.
Lipa sings, “Talkin’ in my sleep at night, makin’ myself crazy (Out of my mind, out of my mind). Wrote it down and read it out, hopin’ it would save me (Too many times, too many times.) My love, he makes me feel like nobody else, nobody else. But my love, he doesn’t love me so I tell myself, I tell myself.” On this track, it’s clear that Lipa’s love is not being reciprocated.
So Lipa has taken it upon herself to create a set of new rules to get over her man. Lipa sings,
One: Don’t pick up the phone
You know he’s only callin’ ’cause he’s drunk and alone
Two: Don’t let him in
You have to kick him out again
Three: Don’t be his friend
You know you’re gonna wake up in his bed in the morning
And if you’re under him, you ain’t gettin’ over him
Overall, this heartbreak song covers a side we don’t often see in similar songs; a method to succeed and a way to avoid additional hurt. Lipa does a fabulous job covering these new rules to avoid staying attached to a former lover, and this may be applicable to people in similar situations—with a broken heart and no guidance.
“New Rules” makes my top list of heartbreak songs because it teaches young woman how to decrease the pain and focus on what is important: independence and happiness.
The Lights Went Out in Georgia by Reba McEntire
The song “The Lights Went Out in Georgia” by Reba McEntire is one of the best songs about I have ever heard. It may not be immediately understood, but examining the lyrics and analyzing the meaning makes you unpack additional layers within this song.
He was on his way home from Candletop
Been two weeks gone and he thought he’d stop
At Web’s and have him a drink ‘fore he went home to her
Andy Wo-Lo said, “Hello”
He said, “Hi, what’s new?”
And Wo said, “Sit down, I got some bad news that’s gonna hurt”
Said, “I’m your best friend and you know that’s right
But your young bride ain’t home tonight
Since you’ve been gone, she’s been seeing that Amos boy, Seth”
Now he got mad and he saw red
Andy said, “Boy, don’t you lose your head
‘Cause to tell you the truth, I’ve been with her myself”
That’s the night that the lights went out in Georgia
That’s the night that they hung an innocent man
Well, don’t trust your soul to no backwoods Southern lawyer
‘Cause the judge in the town’s got bloodstains on his hands
The lyrics above clearly describe a situation involving infidelity and a betrayal of trust. The poor man has been betrayed by his woman, his best friend, the local Judge, and is filled with heartbreak and anger.
Overall, this song recorded my McEntire in 1991 (a rendition of the original version by Vickie Lawrence) was meant to describe a cheating wife. However, it covers so much more. It addresses a lack of trust in law enforcement and the government, as well as noting the hurt of disrespect and infidelity.
The song is really expressing so many topics that they cannot all be covered, but it certainly indicates that an innocent man was hung due to the entire community cheating him, including his woman. It also makes note that the judge had blood on his hands, meaning he was involved in the scandal full of lies and deceit.
If this is not a killer heartbreak song, I don’t know what is.
Call Out My Name by The Weeknd
The song, “Call Out My Name” by The Weeknd is a popular hit, and a sincere heartbreak song. The song is about a man struggling to let go of a previous relationship that was not what he had thought it would be. He sadly feels as though he was simply a pit stop for the woman—not a longterm destination.
The Weeknd sings: “We found each other. I helped you out of a broken place. You gave me comfort, but falling for you was my mistake.” This indicates that he is taking the blame for helping his woman in her time of need. It’s also paints a picture of his lady not fully appreciating what he brings to their relationship.
This song can reach listeners of many genres because it is so touching and relatable. Instead of protecting his pride, The Weeknd openly sings of his loss. It is a brave and bold move.
It is also strangely noteworthy that, because of lyrics in this song, some people speculate that The Weeknd considered donating his kidney to Selena Gomez.
“I said I didn’t feel nothing baby, but I lied – I almost cut a piece of myself for your life.”
Ultimately, Gomez’s donor ended up being her personal friend (Francia Raisa).
Break Up in a Small Town by Sam Hunt
In this popular country song about heartbreak, “Break Up in a Small Town,” Sam Hunt describes the challenges of breaking up in a small town in this highly unique breakup song.
The song expectations are clear based on the title, as Hunt writes:
The title explains everything you would expect about the song. It’s just about growing up in a small town and you break up with a guy or a girl, and you think you’re not gonna see ’em again,” he explained.
“You think they’re long gone, but then you realize there’s just so many streets and so many lights. You hang out with all the same people. They’re the first person you see when you leave the house, so it’s kind of hard to get away from ‘em.”
These lyrics hit on the immense complexities involved when it comes to avoiding your ex in a small town. It’s honestly something that many of us who grew up in large metropolitan cities would never to.
The first verses indicate the expected struggles, but the realization that she would get over him by getting down with somebody he knows was unforeseeable. He claims, “I should’ve known all along you gotta move or move on when you break up in a small town.” This indicates that he feels like he should have known and failed to realize what would happen when he let her go.
The lyrics further address how, “She was over me before the grass grew back where she used to park her car – She’s leaving those same marks in someone else’s yard – In someone else’s arms right down the road.”
This attests to how quickly she moved on and how he feels like he cannot leave home without finding heartbreak. He indicates numerous times how he didn’t expect her to get over him the way he did. He says, “I should’ve known all along, you’ve gotta move and move on, when you break up in a small town.”
Give It Away by George Strait
This song won both the “Single Record of the Year and Song of the Year” at the 2007 Academy of Country Music Awards. And when it comes to the topic of heartbreak, George Strait hits this one right outta the park.
The beginning lyrics tell us a story of a woman leaving Strait. But unlike most songs, which talk about massive infidelity or focus on verbal arguments, this song paints the picture of a very sad breakup through the lens of one’s physical possessions. And it’s amazing how effective this is.
I’ve got furnished house
A diamond ring
And a lonely, broken heart
Full of love
And I can’t even give it away
Hopefully you’ve enjoyed this article detailing some of my favorite songs about heartbreak. If you’ve discovered one or two new songs you’ve never heard before, be sure to head over to your local streaming service (or vinyl record store) and add these songs to you regular playlist rotation (especially if you’re ever in need of some comforting music to help you get over a recent breakup).
This article was written by Lillian, with two select additions by Michael.
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