20 Most Heartbreaking Songs Of All Time

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Our 20 most heartbreaking songs of all time article at times became an emotional roller coaster to write. It actually took me a while to write this because I had to walk away quite a few times. Some of these songs really hit close to home for me, and I know they will for you. The older you get in life, the more heartbreak you experience. Of course, the goal is to get through life in the most joyous fashion you can imagine. But that’s not easy to do. It’s probably almost impossible.

Heartbreak comes in many ways. When you’re younger, especially during your teen years and 20s, it usually comes via Romance. There’s nothing worse than a breakup. It’s not easy to see the one you love not love you or at least I love you anymore. As you get older, you start to think about the ones that got away. We see that especially in songs like Dan Fogellberg’s “Old Lang Syne,” which is on this list. There is a fine line between songs of heartbreak and sadness. Where one begins and ends is often blurred.

This article and this list are not meant to make you sadder. Their goal is the same as these songs have always been. It is to make you feel that you’re not alone. That you’re not the only one who’s experienced heartbreak. Because of these songs, we all recognize that shared experience, and somehow it makes us feel a little less heavy, and maybe even fills us with hope, or maybe more of a sense of melancholy instead of despair. That’s what these songs do and it’s one of the reasons why I started this website many years ago.

# 20 – The Famous Final Scene – Bob Seger

A really well-written song about heartbreak doesn’t need the lyrics to tell you what it’s about right away. A heartbreaking song starts out first, with a riff a melody that just please heartbreak. You could hear it right away in this one. The groove, the piano playing it’s all very sad. But the heartbreaking moment, that instant second where you know this is a sad one, occurs as soon as that guitar starts to cry. You’re already feeling it, and Bob Seger hasn’t even said a word yet. Yes, that’s how to start this list: with one like this.

Bob Seger’s “The Famous Final Scene” was released on his album Stranger in Town. The album was released in 1978. It is one of his most successful albums. It spawned huge hits. Songs that became ingrained in culture, like “Old Time Rock and Roll” and “We’ve Got Tonight.” It is a hard-rocking album full of good times and emotions. And yet he decided to close it out with one of the most heartbreaking songs I’ve ever heard. I think he was sending a message there. It was pretty brave to end an album like that.

Read More: Top 20 Bob Seger Songs

# 19 – For No One – The Beatles

When you think of Paul McCartney, you hear a voice and an artist who writes happy music. So many of his songs have brought great joy to millions of fans from the very first Beatles album to his most recent. He’s one of the most positive people I have ever watched from afar. Seems to never have anything bad to say about anybody. But of course, he’s written some sad songs. Yesterday was one of the saddest. Nonetheless, I think many people miss this one.

Paul McCartney’s “For No One” was released on the great Revolver album. This is the album many people feel may have been the Beatles’ best. It’s filled with iconic songs. And perhaps that’s one of the reasons why this one gets overlooked. Not by Beatles fans, of course; Beatles fans know every song inside and out.

The line that gets me in this song right away is when Paul McCartney sings, “And in her eyes, you see nothing.” Anyone who’s ever been through that before knows exactly what he’s talking about. The other person doesn’t have to say a word; you can see it. That’s so much of McCartney’s genius; his songs are so universal.

This song is about the end of a relationship. Yet even in this song, the bouncy melody suggests some hope. That’s McCartney. He never gives up; think about what he’s been through. The losses that he has suffered. And yet he’s still smiling.

# 18 – Same Old Lang Syne – Dan Fogelberg

For anyone who’s ever made the mistake of letting their soulmate, the one woman or man they loved more than anyone else, walk away, this song reminds you of that mistake. For that reason alone, it is one of the most heartbreaking songs to listen to. It really confuses me why we still listen to it, because it’s very painful. He’s talking about that man or woman you let go of, the person you wish you hadn’t made that mistake with.

What Dan Fogelberg does so perfectly with this song is the setup. On Christmas Eve, he accidentally runs into the one that got away in the grocery store. It’s a place so unexpected to meet someone from the past, yet the perfect setting to take a normal day and turn it into something extremely special.

They sit in her car, have a few drinks, and talk about the past. Then she admits she’d like to say she loves the man she married, but she can’t. That makes it even more difficult. It proves the mistake even more costly.

The most heartbreaking moment of this song is the end. It’s the most heartbreaking and yet cinematically perfect moment. They say goodbye, probably never to see each other again, and as he turns to walk home, the snow turns into rain. Oh, does that hurt. I probably should have put this at number one, but I had to get it out of the way.

Read More: Top 10 Dan Fogelberg Songs

# 17 – Hurt So Bad – Linda Ronstadt

Mad Love (180 Gram Audiophile Pink Vinyl/Limited Anniversary Edition)

This list is filled with songs that definitely affected me the first time I heard them. Granted, I was a teenager and pretty emotional, but you could argue that now that I’m in my sixties, these songs still have that effect. That scares me a bit, but it also confirms to me that they really do break your heart.

Linda Ronstadt recorded “Hurt So Bad” for her 1980 album Mad Love, produced by Peter Asher. Teddy Randazzo, Bobby Weinstein, and Bobby Hart wrote the song, which had already been a hit for Little Anthony and the Imperials in 1965. Ronstadt turns it into a bigger rock ballad without losing the desperation at the lyric’s center.

Danny Kortchmar’s guitar gives the arrangement a harder edge, but Ronstadt’s vocals own the record. Her version reached number eight on the Billboard Hot 100 and became her final solo top-ten hit on that chart. She sounds less like someone remembering an old breakup than someone standing directly in front of the person who caused it.

# 16 – Heartbreaker – Led Zeppelin

Well, we are a rock and roll site, so the list will be heavily dominated by rock bands; it’s just what we do. Not everything will be rock, but Led Zeppelin wrote a song called Heartbreaker and this is our list of the 20 most heartbreaking songs of all time, so yeah, this was going to be included.

Led Zeppelin’s “Heartbreaker” opens the second side of Led Zeppelin II, released in 1969. Jimmy Page, Robert Plant, John Paul Jones, and John Bonham share the writing credit, with Page also producing the recording. The main band performance was recorded at A&R Studios in New York, while Page cut the famous unaccompanied guitar break separately to give it a completely different sound.

The riff is so dominant that it is easy to overlook Plant’s lyric about betrayal and a woman who has left the singer behind. Zeppelin turns that heartbreak into anger rather than self-pity, with Bonham and Jones hitting almost as hard as Page. For a list like this, it is difficult to finish anywhere else.

# 15 – Ellis Island – Mary Black

While Mary Black has never been a household name in the United States, she is definitely one of Ireland’s most beloved artists. I had never heard of her before, but I was listening to the radio one day and this song came on. It was written by Noel Brazil. It was actually a live version by Mary Black that was simply stunning. I think it was WUSB, Stony Brook University’s radio station, because commercial radio usually ignores music like this.

I remember pulling over because the lyrics hit me hard. It’s the story of immigration. It’s the story of the United States, captured in the words of Emma Lazarus on a plaque in the Statue of Liberty’s pedestal: “Give me your tired, your poor, your huddled masses yearning to breathe free.”

What’s missing in that inscription is that many people who came to the United States, who first landed at Ellis Island, left family behind. It wasn’t family they left behind for a trip. It was family they would probably never see again. That is where the heartbreak is.

Just imagine saying goodbye to your parents or your children, knowing you will never see them again. Every person living in the United States is somehow tied to this, even if they don’t realize it.

# 14 – God Give Me Strength – Elvis Costello and Burt Bacharach

As you get older, it gets harder to find new music you can relate to or enjoy. It’s harder to find a new album that you’ll spin on your turntable or play in your CD player like you did with the albums you grew up with as a teenager or in your twenties. But every once in a while, somebody puts out an album that just blows your mind.

That happened to me in the late 90s when Burt Bacharach and Elvis Costello teamed up to release Painted from Memory. The album turned out to be a byproduct of the song I’ve listed here. The two wrote “God Give Me Strength” for the 1996 film Grace of My Heart, and the collaboration worked so well, and the song was so stunning, that an album came out of it.

Everything about this song will break your heart: the melody, the lyrics, the arrangement. Yet its most striking value as a heartbreaking song, for lack of a better description, is Elvis Costello’s vocal performance. From a technical standpoint, I never realized how good a singer Elvis Costello was.

But it’s the pain in his voice, the heartache, that really cuts right through you. This is one of the most stunning ballads released at the end of the 20th century.

# 13 -Yesterday When I Was Young – Charles Aznavour

I was 13 years old when my father brought this album home in 1974. I was just starting to get deeply into music beyond hearing it on the radio. What I remember most about this album, and this song in particular, was my father’s reaction to it.

He wasn’t that old at the time, probably his late 30s, but I saw how it affected him. Of course, when you’re only 13, you’re not really thinking about your past. You’re not even thinking much about your future beyond some fantasy dreams of being an NFL player or a rock star. You’re pretty much just living in the present.

What’s heartbreaking about this song is that someone is looking back on their life and realizing how fast time goes. In that recognition is the sense that maybe they didn’t do everything they wanted to do, or never took the time to stop and look around.

Life can be hard, and we all get wrapped up in paying bills. We can forget sometimes to just feel the beauty in life. Maybe sometimes that beauty has been sucked out of us for many different reasons.

But in the end, as you get older, and I’m 65 now, you do recognize that you can’t get the time back. That’s what makes listening to a song like this a little difficult, but also so necessary.

# 12 – Candle in the Wind 1997 – Elton John

The passing of Princess Diana broke the heart of a nation and a large part of the world. Her death was so tragic, and her loss so monumental, that no poem, story or book could capture the pain so many people felt.

Yet Elton John and Bernie Taupin were able to pay tribute to that heartbreak in an incredibly touching and loving way that it seemed only Elton and Bernie could. They rewrote the lyrics to his 1973 song about the late Marilyn Monroe to honor the life of Princess Diana.

Elton was very close to Princess Diana. When he performed the new version at her funeral at Westminster Abbey, you could see it in his eyes and hear it in his voice. Like so many of these songs about heartbreak, there was also a touch of consolation in his performance.

The song was released as a single for charity, which in its own way paid tribute to all the charitable work Princess Diana had done throughout her life. It sold about 33 million copies, with the money going to her memorial fund.

This is a heartbreaking song, and Elton John said he would never sing this version again unless her sons asked him to. He has kept that promise. He was truly moved, as was the rest of the world, by this heartbreaking moment in history. Princess Diana will never be forgotten.

11 – Pale Blue Eyes – The Velvet Underground

This one has a lot of pain. Sadly, the pain comes from many different parties. The song is about falling in love with someone who is married.

Most people look at the two characters involved: the man who fell in love with the woman, and of course, the woman who is married. They have a relationship with each other.

Yet the heartache, the real heartbreak in the song and the story, isn’t about a couple who can’t continue. It’s about the woman’s husband, the one who is betrayed. Once he finds out, no amount of counseling or apologizing will ever erase that betrayal, and he will hate her for the rest of his life. That is true heartbreak.

The song was written by Lou Reed and released in 1969 on the album The Velvet Underground. It is said to have been inspired by Shelley Albin, Reed’s first love, who was married to another man at the time.

# 10 – Heartbreaker – Pat Benatar

Pat Benatar released “Heartbreaker” on her 1979 debut album In the Heat of the Night, and it became the record that broke her through in the United States. Geoff Gill and Cliff Wade wrote the song, which had first been recorded by British singer Jenny Darren. Benatar adjusted a few of the original British phrases, but the song’s attitude stayed intact. Mike Chapman and Peter Coleman produced her version, with Neil Giraldo helping give it the hard guitar sound that became central to Benatar’s early records. “Heartbreaker” reached number twenty-three on the Billboard Hot 100. It is less a sad ballad than a warning shot from someone who knows exactly who hurt her.

Read More: Top 10 Pat Benatar Songs

# 9 – How Can You Mend A Broken Heart – Bee Gees

The Bee Gees released “How Can You Mend a Broken Heart” in 1971 as the lead single from Trafalgar. Barry and Robin Gibb wrote it after a difficult period when the brothers had been apart, so the song came from real tension within the group. The recording is slow and spare, leaving plenty of room for Barry Gibb’s lead vocal and the brothers’ harmonies. It became the Bee Gees’ first number-one single in the United States and stayed at the top of the Billboard Hot 100 for four weeks. The title asks a question the song never really answers. That is part of why it still works: sometimes heartbreak does not come with a solution.

Read More: Top 10 Bee Gees 1970s Songs

# 8 – Without You – Harry Nilsson

You know I couldn’t put together a list of the most heartbreaking songs of all time without including this classic from Harry Nilsson. It’s the definitive one-that-got-away song. He had her, and then he let her go.

The song was written by Pete Ham and Tom Evans of Badfinger, who first recorded it in 1970. But it was Nilsson’s version that made it immortal, spending four weeks at No. 1 in early 1972.

The song’s opening piano comps, with Nilsson singing in his beautiful tenor, capture the listener instantly. I know it did me. Still, as breathtaking as the intro and first verse are, the killer hook in the chorus slams you with heartbreaking pain. I don’t think there is a more emotional vocal performance in such a heartbreaking song.

Nilsson’s vocal hits such high notes that some of the greatest female singers have taken it on. Heart covered it in the 1970s, and Ann Wilson is probably the greatest female rock vocalist of all time. Of course, the ultimate diva, Mariah Carey, took it on in the 1990s and had a big hit with it. Still, the ultimate heartbreaking version remains Harry Nilsson’s.

Read More: Top 10 Harry Nilsson Songs

# 7 – It’s A Heartache – Bonnie Tyler

Bonnie Tyler released “It’s a Heartache” in late 1977, and the song became her first worldwide smash. Ronnie Scott and Steve Wolfe wrote it, with David Mackay joining them in the production. Tyler’s rough voice was perfect for a lyric about depending on someone who finally lets you down. The single reached number three in the United States and number four in the United Kingdom while topping charts in several other countries. There is nothing complicated about the writing, and that is exactly the point. “It’s a Heartache” says what heartbreak feels like in plain language and lets Tyler’s voice do the rest.

Read More: Top 10 Bonnie Tyler Songs

# 6 – Never Be You – Maria McKee

Maria McKee recorded “Never Be You” for the 1984 Streets of Fire soundtrack. Tom Petty and Benmont Tench wrote the song, and Jimmy Iovine and Petty produced McKee’s recording. Petty and Mike Campbell play guitar on the track, with Tench on piano and Stan Lynch on drums, giving it a strong Heartbreakers connection. McKee sings it with the kind of open, wounded force that would later define so much of her work with Lone Justice and as a solo artist. Rosanne Cash later recorded the song and took her version to number one on the country chart. McKee’s earlier performance is rougher and less polished, which makes the song’s disappointment hit even harder.

# 5 – Pain In My Heart – Otis Redding

“Pain in My Heart” became the title track of Otis Redding’s 1964 debut album. The song is credited to Naomi Neville, the pen name Allen Toussaint used, and is based on his earlier composition “Ruler of My Heart.”

Redding recorded it at Stax with musicians including Steve Cropper, Booker T. Jones, Al Jackson Jr., and the other players who helped define Memphis soul. The lyric is simple: his baby is gone, he cannot sleep, and the pain will not leave him alone. Redding doesn’t sing it quietly or politely; he sounds like the loss is happening as the tape rolls. That urgency is what made his early ballads so powerful.

# 4 – Bad Liver And A Broken Heart (In Lowell) – Tom Waits

Tom Waits recorded “Bad Liver and a Broken Heart (In Lowell)” for his 1976 album Small Change. Waits wrote the song, and Bones Howe produced the album during sessions at Wally Heider Studios in Hollywood. The narrator drinks his way through a breakup, making jokes that barely cover how miserable he is.

Jim Hughart’s bass, Shelly Manne’s drums, and the small jazz setting leave Waits plenty of room to sound like a man telling the story from the last bar stool in the room. The song is funny in places, but the humor never hides the fact that the relationship has wrecked him. Few heartbreak songs manage to be this sad and this entertaining at the same time.

# 3 – In The Wee Small Hours Of The Morning – Frank Sinatra

Ask anyone who has been left with a broken heart, and they will tell you that the thing they fear the most is often going to sleep. Usually because they can’t. They lie awake in bed, staring at the clock. Looking at the window. Fighting furiously to pass out. Yet the pain, the loss, the One That Got Away just keeps constantly ticking, ticking, ticking at your heart. It’s why this song is so perfect. It’s the ticking of the clock that matches the constant beat of pain.

This heartbreaking song was first released in 1955 as the title track of Frank Sinatra’s album, In the Wee Small Hours of the Morning. The song was written by David Mann and Bob Hillard. Hundreds, if not thousands, of artists have recorded it over the years, with Julia London’s version probably the most famous outside Frank Sinatra’s.

Read More : Complete List Of Frank Sinatra Songs From A to Z

# 2 – Heartbreaker – Grand Funk Railroad

Grand Funk Railroad put “Heartbreaker” on their 1969 debut album On Time. Mark Farner wrote the song before Grand Funk was formed and later called it his first real attempt at songwriting. The track begins as a slow, heavy breakup song before opening into the kind of guitar-driven attack that made the early band so powerful live. Farner sings about a woman who is gone but still shows up every time his memories come back. Mel Schacher’s bass and Don Brewer’s drums give the song a weight that keeps it from becoming a conventional ballad. It is heartbreak played by a power trio that has no interest in sounding delicate.

# 1 – Wake Me Up When September Ends – Green Day

As a New Yorker who used to work in the World Trade Center as an entertainer doing a lot of weddings, I thought this song was about the September 11th attacks when I first heard it. I eventually discovered it wasn’t, but I still think it has meaning, and it will always remind me of that day.

The song was released as a single in 2005, just four years after the 9/11 attacks, and I was not the only one who thought it was about that day. But it turned out to be about the death of Billie Joe Armstrong’s father when Billie Joe was just ten years old. It’s tough to lose a parent when you’re a young kid. That loss never goes away.

And that’s where the connection to 9/11 is formed. So many kids lost their mothers and fathers that day. So many people lost husbands, wives, and children. Losing a loved one is the most heartbreaking experience anyone can ever deal with in life.

I was 40 years old in September of 2001. My second son was born the following month. It was a scary time. Yet when I saw how New Yorkers came together, how people around the country who had always kind of been wary of New Yorkers came to our aid, how the city rose above the fear, politics, and race to be just one people, I saw a hope in mankind that I had never seen before.

When someone writes about it and shares that experience in a song, there is some kind of comfort taken from the music, because it’s a shared experience, and that always helps. That’s where heartbreaking songs become essential tools in living life.

Don’t miss our fun, in-depth article on the Top 500 Classic Rock Songs Of All Time

If you’re a fan of 1970s rock, check out our 100 Essential Albums From The 1970s article. You will love that one.

Or try our 100 Greatest Rock Songs Of The 1970s article.

If you want to discover some bands you may have never heard of or simply forgotten about, try our 100 Greatest Rock Bands Of All Time article. That is one of our best.