Top 10 Sad Songs That Make You Cry

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

Other Articles you Might Like