15 Sad Songs That Make You Cry

We’ve all got those songs that strike a chord and get the tears flowing, but what are the saddest songs of all time (at least, according to us)? You may be familiar with some of the songs on our list of songs that make you cry, but others are less mainstream. While the heart-wrenching song that really gets you may not be listed below, feel free to check out any of these tearjerkers when you’re in need of a good cry.

Some of the songs on this list you may be able to relate to personally, and some are just plain sad no matter who you are. No matter which way you look at it, we all like to torture ourselves from time to time with a song that will make us cry.

Leaving no genre untouched, these sad songs that make you cry range from The Beatles to Eric Clapton to Pearl Jam to…well you’ll have to keep reading to see what song tops our list as the saddest of all time.

15. Beck, ‘Lost Cause’ (2002)

Recorded by the multi-instrumentalist and American singer-songwriter in 2002, this depressing track can be found on his breakup album, ‘Sea Change’. With lines like ‘I’m tired of fighting/fighting for a lost cause’, this tale of lost love that isn’t even worth fighting for is relatable for most people who have gone through a painful breakup.

14. Bill Withers, ‘Ain’t No Sunshine’ (1971)

A remarkably beautiful R&B tune, this song is sure to bring on the tears if you actually listen to what Withers is professing. An ode to longing for someone when she is gone, this is one of many sad songs on our list about lost love.

13. Iron and Wine, ‘Naked As We Came’ (2004)

This indie folk tune is a brutally sweet love long, pointing out the harsh truth that one true love always must die before the other. Also included in this song is a nod to cremation, doesn’t get more real than that.

12. Pearl Jam, ‘Last Kiss’ (2006)

Originally recorded by Wayne Cochran in 1961, Pearl Jam wrenchingly takes us through the the last moments with a beloved sweetheart after a rainy date night ends in tragedy. Eddie Vedder’s haunting voice is the final nail in the coffin, so to speak.

11. Sinead O’Connor ‘Nothing Compares 2 You’ (1990)

Originally recorded by Prince, this is one of those songs that will make you cry, as it’s all about how, while life does go on after love, it kind of really sucks.

10. Fleetwood Mac, ‘Landslide’ (1975)

Penned by a young Stevie Nicks, inspiration for this song stemmed from ‘looking out at the Rocky Mountains, pondering the avalanche of everything that had come crashing down on us’. Later covered by country super group, the Dixie Chicks, and the Smashing Pumpkins, Landslide focuses on change and growing in a way that really digs down deep.

9. The Beatles, ‘Yesterday’ (1965)

Probably the most famous song about turning back time and righting old wrongs, The Beatles did what they did best with this one. Beautiful and melancholy, ‘Yesterday’ is centered around the breakup of a relationship.

8. Prince, ‘Purple Rain’ (1984)

This list wouldn’t be complete without a Prince song. Probably the most widely recognized song of his, the lyrics go something like this: ‘honey I know, I know, I know times are changing/It’s time we all reach out for something new/That means you too/You say you want a leader/But you can’t seem to make up your mind’. Once you let those lines settle in, it’s only a matter of time before the tears start flowing.

7. Al Green, ‘How Can You Mend A Broken Heart?’ (1972)

A cover of the Bee Gees’ hit, the Reverend Green poses a reasonable question. The soulful, silky nature of this song may be deceiving, but it’ll get you where it counts just the same.

6. R.E.M, ‘Everybody Hurts’ (1992)

Included on the band’s 1992 album, Automatic for the People, this over-popularized but still devastating song really hits home. Between the swooning swing section and Michael Stipe’s haunting vocals, this song owns its #6 slot of sad songs that will make you cry.

5. Otis Redding, ‘I’ve Been Loving You Too Long’ (1965)

Perhaps the most soulful song ever, Redding’s rasp makes it sounds like he had been crying his eyes out before cutting the track. Coupled with the blaring horn build-up, this song feels like a punch in the stomach that you just can’t quite recover from.

4. George Jones, ‘He Stopped Loving Her Today’ (1980)

This classic country crooner doesn’t hold anything back with the 1980 hit, ‘He Stopped Loving Her Today’. Hitting home with a tune about a jilted lover carrying the memory of an old flame ’til his deathbed, this is is by far one of the saddest songs to date.

3. Eric Clapton, ‘Tears in Heaven’ (1992)

Perhaps the most personal song on our list, the guitarist penned this 1992 hit in response to the accidental death of his 4-year old son. Devastating to say the least, this song touches on the chasm that is left between Clapton and his son, it really doesn’t get any sadder than that.

2. Hank Williams, ‘I’m So Lonesome I Could Cry’ (1949)

Arguably the saddest song of all time, this mournful tune riddled with a sobbing fiddle and heart-wrenching lyrics may make you want to shut the lights out forever right then and there. This song focuses on loneliness and is largely inspired by a previous marital experience, making it all the more relatable to many listeners.

1. Johnny Cash, ‘Hurt’ (2002)

Rounding out our list of sad songs that will make you cry is the Man in Black himself, Johnny Cash. It was released in 2002, in response to Cash’s long battle with the neurodegenerative disease that would eventually take his life a year later.

A cover of the Nine Inch Nails original, this tear-inducing song conjures up feelings of genuine loss and heartache. The music video for this song is considered by many to be Johnny Cash’s Epitaph.