Top 10 Sad Breakup Songs

If you’ve just had your heart pulled out of your chest and then crushed under the foot of a former lover, these top 10 sad breakup songs should provide you some small comfort in knowing that many others have gone through such pain. Chin up, lad, it will all work out for the best.

1. “Album of the Year” by The Good Life. The titular song from The Good Life’s “Album of the Year” is a great example of a sad breakup song from an entire album of great breakup songs. When Tim Kasher sings “We started laughing ‘til it didn’t hurt,” it is one of the most poignant moments ever put to music.
2. “My Broken Heart” by Noah and the Whale. Noah and the Whale’s “The First Days of Spring” is another in a long history of albums inspired by a breakup. It’s both sad and beautiful, two hallmarks of any great breakup album. With its plaintive strings and downtrodden lyrics, “My Broken Heart” is a standout track.
3. “A Perfect Sonnet” by Bright Eyes. Omaha native Conor Oberst has much in common with fellow Saddle Creek labelmate, Tim Kasher. For instance: having written lots of really depressing songs. Although his songs are generally less focused on breakups than Kasher’s, Oberst still hit it out of the park with this song about trying to capture a lost love in one perfect poem.
4. “The Casualty” by Cursive. Speaking of Tim Kasher, he doesn’t just write sad breakup songs for one band. He is even more well-known for his work in the harder-rocking Cursive. Cursive’s “Domestica” is an album that thinly fictionalizes Kasher’s breakup with his ex-wife, a point in his life that obviously had a lot of impact on his music to come.
5. “Summer Skin” by Death Cab for Cutie. Summer romances by their very nature tend to come and go rather quickly, and that sense of fleeting love is perfectly captured by Death Cab for Cutie’s “Summer Skin.” With its wistful imagery of long shadows and squeaky swings, it’s hard not to feel a little forlorn after listening to this tune.
6. “It’s All Over Now, Baby Blue” by Bob Dylan. There has been much speculation about who exactly “Baby Blue” is. In the end, though, it doesn’t really matter. This is still one of the all-time great, sad break-up songs, no matter who inspired it.
7. “Everything Reminds Me of Her” by Elliott Smith. Sometimes, after a breakup, it can be hard to let go. Elliott Smith put that feeling into song with “Everything Reminds Me of Her.” Smith was a prolific writer of sad songs, and this is one of his saddest.
8. “Fight Song” by The Appleseed Cast. “As the tears come out it’s the end, the end of you and me.” With lyrics like that, there’s no mistaking what this song is about. The Appleseed Cast may not be as well known as some of the other bands on this list, but they’re no less adept at writing a good breakup song.
9. “About Today” by The National. Just try listening to any album by The National and not coming away from it feeling gloomy. “How close am I to losing you?” Matt Berninger sings to an unidentified lover in “About Today,” but the answer seems to be that it’s already a foregone conclusion.
10. “Pictures of You” by The Cure. Few musicians do mopey, depressing music better than Robert Smith. This track from the classic “Disintegration” is a classic sad breakup song from one of rock music’s great sad sacks. “If only I’d thought of the right words,” Smith sings, “I could have held on to your heart.” Forgive us if we find it difficult to imagine him at a loss for words.