Top 10 Sad Songs That Make You Cry

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Let’s get one thing straight: I’m a man. A tough-as-nails manly man who lifts weights and watches Sportcenter and kills spiders with my bare hands – unless, of course, I’ve just gotten my nails done. And I am secure enough in my manhood to publicly acknowledge that the following sad songs can make me sob like a jilted prom queen (but, you know, a manly prom queen). Here are my top 10 sad songs that make you cry. What other songs would you add to this list?

10. Way to Blue (Nick Drake)

“Have you seen the land living by the breeze?”


English acoustic brooder Nick Drake lived the kind of short, sad life that seemed designed to produce tear-jerking anthems, and Way to Blue brings on the waterworks like no other in his tragically slim body of work. With a less gifted singer at the helm, the results would have been a strings-laden sap-fest, tailor-made for early 70’s am pop; Drake takes us on a deeper journey – one that doesn’t spare us the scenic route of his broken soul.

9. Mother (John Lennon)

“I needed you. You didn’t need me.”


When the Fab Four parted ways at the close of sixties, the band’s chief frienemies John Lennon and Paul McCartney both saw their divorce as a liberation, a chance to pursue their true artistic callings. For The Cute Beatle this meant finding a home atop Billboard’s charts with a fun but forgettable series of silly love songs. Meanwhile The Smart Beatle sought a nobler path and created some of the most earnest, achingly humorless songs ever put to wax. I guess it’s true that the children (in this case, fans) suffer the most in divorce.

Still Lennon’s solo library is not without a few gems. Mother is not the feel-good hit of the summer, but good luck keeping the eyes dry during this searing ode to parental abandonment.

8. Angel of Harlem (U2)

“Lady Day got diamond eyes; she sees the truth behind the lies.”


Yes kids, before U2 became a bloated, self-important arena rock machine, they could deliver heartfelt, personal tunes, like this love letter to the legendary Billy Holiday.

7. Redemption Song (Bob Marley)

“Emancipate yourself from mental slavery; none but ourselves can free our minds.”


So powerful is the spell that Marley casts with this song of freedom that even his amusingly Jamaican syntax (“Old pirates, yes, they rob I; Sold I to the merchant ships”)
can’t distract us. Give I a hanky, mon. Me wants to cry.

6. Autumn in New York (Billie Holiday)

“So on this gray and melancholy day, I’ll move to a Manhattan hotel.”


Penned and recorded a half century prior to the nightmarish events of September 11th, Lady Day’s touching torch song was obviously not intended as an homage to the darkest Autumn day in New York’s history, but tell that to my (manly) tear ducts.

5. Card Cheat (The Clash)

With a card up his sleeve, what would he achieve?”


Is Mick Jones singing about an actual down-on-his-luck gambler or is there a surprisingly sophisticated metaphor at work here? You be the judge, while I get the kleenex… uh, yeah, there’s something in my eye, that’s all…

4. Already Dead (Beck)

“Days turn to sand, losing strength in every hand.”

This obscure cut from Sea Change (aka The ‘Beck Gets Sad’ album) best embodies its author’s efforts to escape the world of irony-driven dance pop. The broken-hearted Beck doesn’t just confront the grim reaper’s sullen stare; he’s already surrendered to it.

3. She Wanted to Leave (Ween)

“I couldn’t believe… she wanted to leave.”

This unapologetically dorky novelty band — best known for such cannabis-fueled tunes as ‘Touch my Tooter’ and ‘Push th’ little Daisies’ – are fairly unlikely candidates to contribute to this list of tear duct openers. Add to that the awkward fact that ‘She wanted to leave’ is about a pirate having his long-time captive stolen from him and you’d be right to question my sanity for including it. But who knows, maybe this tale of kidnapping on the high seas is really just a metaphor for the enslavement of the human spirit and the unleashing of —

Oh, who am I kidding? It’s just a sad song about pirates.

2. Everyone Says Hi (David Bowie)

“Don’t stay in a sad place where they don’t care how you are.”

What could be more truly heartrending than a cordially phrased open letter to a recently relocated friend, complete with obligatory greetings from all those left behind –especially when the letter’s unspoken subtext is something closer to please, please come back.

1. Big John Shaft (Belle and Sebastian)

“I won’t play another heavyweight; I won’t play another big John Shaft.”

Yes, it’s a song about that Shaft – the black private dick who’s a sex machine all the chicks. Well, kind of. It’s really a tale of a burned out actor fed up with being typecast as – among other things – a cat who won’t cop out when there’s danger all about (right on!).

I’ll never watch Superfly the same way again.

Written by Copper Smith

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373 Comments

  1. Some possibilities from earlier generations:

    Linda Ronstadt: Long, Long Time
    Enya: Exile
    Alphaville: Forever Young
    Michelle Firestone: Coffee & Cigarettes
    Garbage: Cup of Coffee
    Marianne Faithfull: Ballad of Lucy Jordan
    Bette Middler: The Rose
    Patti Smith: Dancing Barefoot
    Janis Joplin: Summertime
    Odetta: All the Pretty Horses
    Dire Straits: Brothers in Arms
    Simon & Garfunkel: Bridge Over Troubled Water
    Fleetwood Mac: Brown Eyes
    Lou Reed: Perfect Day
    Joan Osborne: One of Us
    Natalie Merchant: Which Side Are You On
    John Lee Hooker / Carlos Santana: Things Gonna Change
    Donovan: Wear Your Love Like Heaven
    Mark Anthony: Vivir Mi Vida
    Heartland: I Loved Her First
    Metisse: Boom Boom Ba
    Wasis Diop: Everything Is Never Quite Enough
    Harry Nilsson: Without You
    Bliss: 100,000 Angels
    Pacific Gas & Electric: Are You Ready?
    The Grateful Dead: So Many Roads
    and Ripple
    and half of Leonard Cohen’s library (which has been called “music to slit your wrists to”), but especially:
    Who By Fire
    Hey, That’s No Way to Say Goodbye
    Sisters of Mercy
    Dance Me to the End of Love
    A Thousand Kisses Deep
    Here It Is
    Show Me the Place
    Suzanne

    Those are a few of the songs that always do it for me
    But music is such a personal thing — your mileage not only MAY vary, it absolutely will.
    Cheers.

  2. 1. I Miss You- 5 Seconds of Summer cover
    2. Skinny Love- Birdy cover
    3. The Fault In Our Stars- Troye Sivan
    4. Moments- One Direction
    5. Welcome To The Black Parade- My Chemical Romance
    6. Give Me Love- Ed Sheeran
    7. Small Bump- Ed Sheeran
    8. The Call- Regina Spektor
    9. My Immortal- Evanescence
    10. Sally’s Song- Amy Lee
    11. I Dreamed A Dream- Les Mis
    12. A Little Fall Of Rain- Les Mis
    13. Little House- Amanda Seyfried
    14. Been A Long Day- Rosi Golan
    15. See You Again- Carrie Underwood
    16. Let her Go- Passenger
    17. Curl Up And Die- Relient K
    18. The Scientist- Glee cover
    19. I Will Follow You Into The Dark- Death Cab For Cutie
    20. Gone, Gone, Gone- Phillip Phillips

    These songs are real tear jerkers for me..

  3. I think the songs that everyone listed would make the perfect sad songs collection. Personally with me, I found that I associate songs with certain things and events that happened in my life, and crap I had to go through. I’m sure there are other people like that too. So looking at certain songs from that view point, I can understand how a song can make someone cry, but not the next person. But that is just my view point. Also, how about:

    Nickelback – Lullaby
    Adele – Set Fire To The Rain
    The Connells – 74 75
    Backstreet Boys – Incomplete
    Hoobastank – The Reason
    Kenny Loggins – Meet Me Halfway
    James Arthur – Impossible
    The Mission UK – Butterfly On A Wheel
    Staind – It’s Been A While
    Staind – So Far Away
    Counting Crows – A Long December
    David Grey – The One I Love
    Pink – Try
    O Town – All or Nothing
    Passenger – Let Her Go
    Pat Benatar – We Belong
    Peter Gabriel – I Grieve
    Phil Collins – Against The Odds
    Prime Circle – Turning In My Sleep
    Prime Circle – What I’ve Become
    Reamonn – Supergirl
    Richard Marx – Hold On To The Nights
    Bruno Mars – Grenade
    Heart – Alone