Top 25 Break-Up Songs (you probably aren't listening to)

Where do the lonely and shattered hearts go after a break-up? The only place that’s safe and comforting: to the world of music. Listening to break-up songs is a cathartic, essential and pitiful part of the healing process for the brokenhearted. After the passing of a relationship, most of us need to cry, vent and yell for an indeterminate amount of time without being told to keep it down and get on with our lives (we will!). A break-up song is a perfect companion on those long and insufferable nights when you can’t sleep because it describes in excruciating detail all the pain you’re experiencing. I’m currently nursing a wounded heart, so I’m sort of an “expert” on break-up songs. I’ve created a break-up playlist (what else was I supposed to do?) featuring the top 25 break-up songs you probably aren’t listening to, unless you’re going through a break-up. 



1) Amos Lee “Learned A Lot” Ryan (Amos) is a dying breed. He’s a singer-songwriter with a lot of heart and soul. Everything about this song is therapeutic: his soothing voice, the subtle use of an organ in the background and his reflective lyrics about the lessons heartbreak imparts.  

2) Amy Winehouse “Love is a Losing Game” 

When Amy passed away last summer, we lost a great talent. “Back to Black” is one of my all-time favorite albums because it describes the chaos and disappointment of romantic relationships and chronicles her constant struggles with drugs and alcohol. 

3) Band of Horses “No One’s Gonna Love You” Don’t cringe at the title. Ben Bridwell, lead singer of BOH, has a mesmerizing voice and belts out some of the most poignant and passionate lyrics about a crumbling relationship.

4) Ben Harper “Walk Away” With his bittersweet song, Ben proves that all you need to connect with a heartbroken audience is a guitar and authenticity. If you can make it through 3 minutes and 50 seconds without crying, you’re probably not human.  

5) Bon Iver “I Can’t Make You Love Me” (Bonnie Raitt cover) Cover songs are usually hits or misses, especially if the original song is legendary and timeless. Justin Vernon keeps it simple, graceful and haunting with his delicate piano arrangement. It strikes several chords deep within your broken fiber.

6) Bon Iver “SkinnyLove" 

The first time I came across Bon Iver, I couldn’t pronounce the name. After I listened to the live version of “Skinny Love,” I was no longer in doubt, or quite the same way again. Justin possesses the unique ability to move your soul as he sings with such acute agony the sense of hopelessness that hits you after a rough break-up.

7) Fiona Apple “I Want You” (Elvis Costello cover) 

I’m a huge Fiona fan, so it’s no surprise she’s on my break-up playlist. I’ll never forget how I felt after coming across her live Costello cover almost three years ago. The rage, pain, longing and shamelessness in her voice are a mirror image of what most of us experience as we struggle to come to terms with the dissolution of a relationship.   

8) Fleetwood Mac “Dreams” Stevie Nicks composed the song in 1976 during a time when most of the members of the group where experiencing relationship woes. The track features a lively dance beat, while Stevie sings about releasing a lover who wishes to be set free. Women (and men) will come and go.     

9) Gang Starr “Ex Girl To Next Girl” Guru and DJ Premier were untouchable and unparalleled during the early 1990’s. “Ex Girl to Next Girl” is real talk about what all lovers will one day be: an ex or the next. 

10) Jay Z “Song Cry" 

Who knew Jigga could be so sensitive? On this melodic rap ballad, Just Blaze samples “Sounds Like a Love Song” by Bobby Glenn and Jay Z laments a break-up. Heartache is a universal language.

11) Justin Timberlake “What Goes Around Comes Around” He sings. He dances. He acts. He produces. Is there anything this gorgeous man can’t do? The beat is spectacular (shout out to Timbaland!) and Justin’s otherworldly falsetto serves to emphasize the despair and betrayal of a man who was done wrong.     

12) Keith Urban “You’ll Think of Me” There’s nothing like a good ol’ country song to help cure the blues. This sorrowful song hits close to home for the broken-hearted because Keith clearly knows what pain, sleeplessness and loneliness feel like after a break-up.  

13) Kings of Leon “Closer” While much of the appeal of this once innovative band has worn off, there are still stellar songs on their discography. “Closer” might be a dark and intense song about a vampire, but Caleb’s gritty and tortured voice describes the inner turmoil of the recently bereaved.       

14) Lauryn Hill “Ex-Factor” 

Hip-hop’s reigning queen released one solo album in her lifetime, but it’s enough to remind us why she’s unparalleled. Lauryn has such an emotive voice and she echoes our difficulties in saying good-bye to love.   

15) Mana “Te lloré un rió” One of Mexico’s most beloved and well-know rock bands draw on several musical sounds and styles. Fher is honest and controlled as he sings about the pain one has to endure when love makes an exit. Sometimes break-up songs sound way better in Spanish.

16) Maxwell “Pretty Wings” Maxwell makes music for grownups in love. His stunning and heartfelt voice carries you through every sad, yet hopeful, note on “Pretty Wings.”      

17) Phil Collins “Against All Odds” You can’t have a break-up playlist without adding this iconic song to the mix. In many ways, I think Phil set the bar for break-up songs.

18) Prince “How Come You Don’t Call Me Anymore” B-sides can be such hidden gems. Prince’s bluesy, smooth and at times shrill falsetto serves to underscore the torturing aftermath of a break-up.    

19) Ricky Martin feat. La Mari de Chambao “Tu Recuerdo” 

Ricky first achieved musical prominence with the Latin boy band Menudo during the 1980’s. But it is this sensual yet sorrowful duet with La Mari from the Spanish flamenco-electronic band Chambao that remains one of my all-time favorite break-up songs.

20) Ryan Adams & The Cardinals "Fix It" 

Ryan was originally part of the group Whiskeytown but things really took off for him once he went solo. I prefer the live version of “Fix It” because his voice absolutely bristles with pain and regret.

21) Skyzoo “Dear Whoever” Skyzoo excels at metaphors. Listen closely to his track about an apparent break-up. His raw and honest lyrics catch you off-guard.  

22) Stereophonics “Rainbows And Pots of Gold” 

This song is what you wish you could tell your former lover. Kelly executes every line with the perfect amount of pain.

23) The Decemberists “Engine Driver” Whether you love or hate his voice, most of us can agree that Colin is an exceptional writer. The hook leaves you breathless even though it’s deceptively simple.

24) The Mars Volta “Since We’ve Been Wrong” There’s never a dull song with The Mars Volta. Omar’s guitar practically weeps and Cedric’s voice gives you goose bumps as you contemplate a past that no longer exists.   

25) Ween “It’s Gonna Be (Alright)” For such an eclectic and eccentric band, Ween does a hell of a job composing a break-up song. “It’s gonna be alright”: it’s a phrase we constantly tell ourselves after a gut-wrenching loss.




Honorary mention: The Procussions feat. Talib Kweli "Miss January"

The now-defunct hip-hop act from Colorado Springs teamed up with hip-hop's greatest poet, Talib, to produce a song about letting go and embracing the future.