If you need a good cry, these songs will absolutely wreck you

Have you ever wondered why so many people enjoy listening to sad music? It’s not for everyone, of course – some people don’t like scary movies or thrilling rides either. But clearly, all these things have a dedicated following, and it’s interesting to consider why.

You know, I was thinking about something and I’m still trying to figure it out. I have this fuzzy idea, and it’s kind of like why we love scary movies or roller coasters, but not quite the same. I think it’s about letting off steam, you know? We all know how life goes, and we all know it doesn’t last forever. Maybe facing that, in small doses – like with a good movie, a thrilling ride, or even a song – is how we cope with it all.

Music has a special ability to deeply move us. It connects with our emotions in a powerful, almost physical way. While there are scientific explanations for this, most of us simply feel it – a tune can affect us far more profoundly than ordinary thoughts or feelings.

20 sad songs to brighten your day

When you combine compelling storytelling with beautiful language, you create something truly impactful. Music acts like a gateway, letting those words resonate deeply within us.

Anyway, that’s my notion.

We’ve put together a list of twenty incredibly sad songs from recent popular music. It’s impossible to create a perfect list, as there are just so many songs out there. I even thought about focusing on a particular style or theme – like the most heartbreaking rock songs about loss – but decided against it.

But I rejected that. It felt too limiting.

Here’s a diverse collection of songs, covering different genres, topics, and time periods. To make things more engaging, I’ve chosen them in pairs instead of listing twenty individual tracks – you’ll find ten pairings, grouped by…

You know what? You’ll see for yourself.

Break-ups

“For No One” by the Beatles (1966) and “A Good Year for the Roses” by various

Love is the most popular subject for songs, and heartbreak is a classic theme for sad ones. Picking the best two songs on these themes feels impossible – it’s like trying to choose your favorite grains of sand! – but I’m happy with these selections.

Paul McCartney’s song “For No One” beautifully blends a memorable melody with simple, yet powerful, lyrics. It perfectly captures the pain of a relationship ending when one person grows and changes while the other stays stuck. The song’s final verse is remarkably concise and emotionally resonant.

While you stay in, she goes out. She mentions a past relationship, someone she used to know, but says she’s moved on and doesn’t need him anymore.

Plus, there’s that utterly expressive French horn.

Jerry Chesnut originally wrote the song “Good Year for the Roses,” but George Jones popularized it in 1971. I’ll also mention Elvis Costello’s beautiful rendition of the song, which came out a decade later, as it’s relevant to what I’ll be discussing.

Whether you like it or not, Chesnut skillfully contrasts everyday household tasks with a family falling apart, creating a powerfully sad impact. Exceptional singers deliver even the simplest lines with incredible emotional depth, for example:

“After three full years of marriage
It’s the first time that you haven’t made the bed.”

Break-ups, part 2

“April Come She Will” by Simon & Garfunkel (1966) and “Simple Twist of Fate” by Bob Dylan (1975)

These songs don’t just dwell on heartbreak; they offer a different approach. Instead of starting with the breakup itself, they show how the relationship began and flourished, making the eventual end feel even more poignant and sad.

Paul Simon composed “April Come She Will,” but Art Garfunkel was the lead vocalist – a rare occurrence for him. His gentle tenor voice perfectly captured the song’s delicate emotions, much like he would later do on “Bridge Over Troubled Waters.” The way he sings the final lines is both simple and deeply moving.

It feels like summer is slipping away, and I’m already dreading August – it just feels like something’s ending. The changing weather is a reminder, with those chilly autumn winds. I’ll always remember September, though, because it marks a time when a relationship felt so fresh and new, but now… well, it’s just faded with time.

Dylan, true to his style, crafts a film-like depiction of one night that endlessly troubles a man’s mind.

He woke up to an empty room, and she was nowhere to be found. He tried to convince himself it didn’t bother him, and then he opened the window wide.

Death of a lover

“Eli the Barrow Boy” by the Decemberists (2005) and “Elephant” by Jason Isbell (2013)

It’s natural for songs to be about death, and losing a loved one is a particularly common theme. The challenge is to write about it without being overly emotional. Luckily, these songwriters have the talent to pull it off.

I’ve always loved Colin Meloy from the Decemberists, and it’s amazing to see his storytelling shine in his children’s books too. This story of Eli is so beautifully simple, and you can really feel his style in the gentle acoustic music. He sings about this boy, Eli, and his love, sometimes talking as Eli and sometimes about him, as he follows his beloved even into death. It’s a really sad story, of course, but Meloy is so good at keeping it grounded in the little details, which prevents it from becoming overly dramatic. He just tells the story, and it’s incredibly moving because of that.

“Below the tamaracks he is crying
Corn cobs and candlewax for the buying
All down the day”

Jason Isbell’s song features a simple acoustic guitar arrangement with subtle additions. It’s about a couple coping with a loved one’s impending death, and the song’s title represents their attempt to ignore the difficult reality they’re facing.

When intoxicated, she would tell inappropriate jokes about cancer and even forge medical documents. Despite being with her family, it was clear she was facing her final moments in isolation.

Death

“Jackie” by James McMurtry (2021) and “Middle of the Heart” by Adeem the Artist (2022)

There’s a lot of potential when it comes to songs about sadness. I’ve chosen two newer ones that aren’t quite as famous as a classic like “Eleanor Rigby.”

Larry McMurtry is one of the best songwriters in America right now. His songs are known for telling fully realized stories, and this one—about a truck driver who secretly dedicates her life to raising horses—is particularly moving. I admire his ability to write such powerful and descriptive lyrics.

I heard about this terrible accident – a truck driver lost control on some black ice while carrying a really big load. It’s so sad, there’s a memorial now where her rig went off the highway. It just breaks your heart to think about it.

Adeem’s album, White Trash Revelry, is a powerful emotional journey. It ranges from the energetic and wild track “Going to Hell” to the heartbreaking “Middle of the Heart,” a song about a kind-hearted young man transformed into a soldier and trained to kill for his country.

“Nights get longer
Days get hard
I learned to put a bullet through the middle of a heart.”

Spritual stagnation

“Fast Car” by Tracy Chapman (1988) and “The Girl in the Picture” by Ashley McBryde and Pillbox Patti (2022)

I’m not saying men don’t experience creative blocks, but I’ve noticed something interesting: all eight of the songs I’ve written about so far were created by male artists. I think this might reveal a pattern in my own tastes, and honestly, I’m aware it could seem a bit progressive to point that out.

I originally wrote a really sad song about this – called “The Ballad of Lucy Jordan.” A man wrote it, but a woman made it famous in 1979. I ended up choosing a different song, and you’ll understand why as we go on…

“Fast Car” is a truly unforgettable song, and it’s no surprise it’s on this list. What makes it so powerful isn’t a dramatic event like a breakup, illness, or loss, but rather its ability to capture the quiet disappointment and longing found in ordinary life. Tracy Chapman perfectly conveys that feeling of unfulfilled dreams like few other artists have.

Man, this song just hits different. It’s about wanting to escape, you know? Like, you’ve got the means to get out of a bad situation – a ‘fast car’ – but you’re wondering if it’s fast enough to really leave everything behind. It’s a tough call – do you risk it all and go tonight, or just accept things as they are and stay stuck? It really makes you think.

Ashley McBryde’s 2022 album, Ashley McBryde Presents: Lindeville, is a fully realized world built with the help of several co-writers. The third song on the album (and the fourth track) tells the story of a woman whose peak moment is being captured in a beautiful photograph. McBryde cleverly reveals her subject’s name for the first time in the song’s bridge, adding a powerful emotional touch.

“Shouldn’t be a prize
For catching the last smile of a girl named Caroline.”

Unequal gender politics

“Caroline Says II” by Lou Reed (1973) and “Unwed Fathers” by John Prine (1989)

Both Reed and Prine acknowledge, through their songwriting, a shared responsibility for how men misuse their physical and emotional advantages in society. Their work reflects a sense of apology for this pattern of behavior.

Although Reed wrote many songs in a similar style, this track from his stark Berlin album is particularly heartbreaking. It tells the story of a woman stuck in a dangerous and controlling relationship, with little hope of escape – the idea of going to Alaska serving as a symbolic representation of finding any way out.

Caroline says, as she stands up, ‘You can hurt me however much you want, but I’ve fallen out of love with you.’

Unlike Reed, Prine shows deep compassion in his depiction of a teenage girl dealing with the aftermath of a sexual experience, while the other person involved faces no repercussions. He portrays her pain with remarkable sensitivity.

“In a cold and gray town
A nurse says lay down
This ain’t no playground
And this ain’t home.”

The bottle

“Tom Traubert’s Blues (Four Sheets to the Wind in Copenhagen)” by Tom Waits (1976) and “Here Comes a Regular” by the Replacements (1985)

Writing songs about drinking can be trickier than writing about sad or serious topics like heartbreak and death. It’s easy for these songs to become overly sentimental or cloying, so it requires a skilled songwriter to pull it off well.

Tom Waits is a brilliant songwriter because he can tell stories without making them feel distant. In this song, his sadness is made worse by being in an unfamiliar place, making him feel like an outsider. He turns to alcohol to cope, which only deepens his loneliness. Keep an ear out – a specific melody from this song will reappear later in another one.

It’s a worn-out suitcase taken to some anonymous hotel, and a pain that will always remain. There’s no glamorous singer here, just the lingering scent of perfume. An old shirt bears the marks of both blood and whiskey.

By 1985, The Replacements were starting to wind down, and honestly, a big part of it was Paul Westerberg wanting to write songs that weren’t just loud punk anthems. For the last song on Tim, he basically did a solo acoustic thing – a really raw, sad ballad about being in a bar. It’s kind of like the opposite of Cheers – instead of feeling good, it’s just… heartbreaking.

“Well a person can work up a mean, mean thirst
After a hard day of nothing much at all.”

Kids

“Luka” by Suzanne Vega (1987) and “Let’s Stay Together for the Kids” by Blink 182 (2001)

You’ve probably noticed a pattern: topics like love, death, and addiction are common in sad songs, but they can easily feel too heavy-handed if not approached carefully. The same is true when writing about children and the difficult things they go through.

Vega mentioned being inspired by the complex themes in Lou Reed’s Berlin, and this influenced her approach to “Luka.” While the song deals with the serious issue of child abuse, many people didn’t immediately recognize that meaning when they first heard it.

The music starts with a lively energy, but there’s a subtle sense of unease underneath. The main character seems odd at first, but quickly becomes unsettling. It’s only by paying close attention that you realize how deeply frightening the story truly is.

“They only hit until you cry
And after that you don’t ask why
You just don’t argue anymore”

Even though Blink-182 had already shown emotional depth in songs like their 1999 hit “Adam’s Song” and other tracks, listeners were still surprised by the maturity of “Let’s Stay Together for the Kids” when it was released.

You know, the album’s called Take Off Your Pants and Jacket, and one song really got to me. It’s written from the perspective of a kid watching a couple struggle in their marriage, and Tom DeLonge really makes you think about the hurt that happens when things fall apart – it’s something so many people go through, and he captures it perfectly.

I have so much bottled up inside, but I can’t seem to express it. My thoughts are decaying, and I feel lost. I wonder if even a beautiful poem could make things better – I’d read it constantly if it could.

Country

“He Stopped Loving Her Today” by George Jones (1980) and “Whiskey Lullaby” by Brad Paisley and Alison Krauss (2004)

I’ve generally steered clear of categorizing music by genre, but I’ll make an exception here. Country music is likely the source of more heartbreaking songs than any other style. While many country songs could be considered incredibly sad, these two really stand out as prime examples.

Jones previously worked on another song featured here – “A Good Year for the Roses,” which is why I brought up Elvis Costello’s rendition. I had a feeling George Jones would appear on this list, as he was famous for bringing deep emotion to his performances. When he sang a truly great song, the effect was remarkable.

This song, co-written by Bobby Braddock and Curly Putnam, is exactly what he delivered. Producer Billy Sherrill also provided crucial support during a challenging time in the artist’s life, helping him create this remarkable track. While fundamentally a song about heartbreak, its emotional power unfolds gradually and deeply.

The singer experienced heartbreak, but his love for her never faded. He carried that love with him throughout his entire life, until his very last day.

I always imagined him as a really sentimental guy, and it turns out I was right. He saved letters from 1962, and get this – he’d gone through and underlined every ‘I love you’ in them! It’s such a sweet, heartbreaking detail, you know? It really shows how much those words meant to him.

“Whiskey Lullaby” is an incredibly sad song, and that sadness is clear throughout the music, the lyrics, and the way the story ends. It’s a powerfully emotional piece, though not particularly nuanced or symbolic. The song brings together themes of heartbreak, drinking, and death, and Alison Krauss’s second verse especially emphasizes how one tragic event can have lasting consequences.

“The rumors flew
But nobody knew how much she blamed herself.”

War

“The Band Played Waltzing Matilda” by the Pogues (1985) and “Al Bowlly’s in Heaven” by Richard Thompson (1986)

I came up with the idea of connecting songs by noticing similarities between them. Specifically, these two songs – by artists from the British Isles and released about a year apart in the mid-1980s – both deal with the lingering pain of an older war, and they both use musical elements to help tell those stories.

Eric Bogle penned the song “The Band Played Waltzing Matilda,” and Shane McGowan delivered a characteristically raw and emotive performance of it – similar to how Tom Waits had incorporated the “Waltzing Matilda” theme into his song “Tom Traubert’s Blues” ten years earlier. The song powerfully depicts the loss of young lives in the brutal reality of war.

I’ll never forget that awful day. The beach ran red with blood, and the sea itself seemed stained. Sulva Bay was a nightmare – we were simply cut down, helpless like lambs being led to slaughter.

Thompson explores similar themes, but centers his story on the difficult life of a disabled veteran long after the war has ended. The narrator remembers Al Bowlly, a popular singer, as a symbol of a more hopeful past when he still had dreams for the future.

“I gave my youth to king and country
But what’s my country done for me
But sentence me to misery?”

If you’re in the mood to cry, give these songs a listen. Then, switch over to Olivia Dean or Olivia Rodrigo – whichever artist you prefer – to lift your spirits. It’ll be a whirlwind of emotions, but thankfully, it’s just music, not real life.

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2026-05-08 14:02