10 Most Tragic Breakup Songs Ever

The honeymoon phase of a relationship is usually around two years. After the initial luster has worn off, two people truly find out what the other is like. The scales have fallen from the eyes and the involved parties, now secure that they are loved, probably don’t try as hard. Both these things mean the reality of your other half is thrown into sharp relief.

What happens when a relationship does not make it past this phase? When love does not endure, and the lovers find they could not, or would not, make things work, then comes the dreaded breakup. This official end normally summons painful heartache for at least one of the two people involved. Just as obsessed as we may have been in the beginning, mooning over the loved one when not together, so the end of love can recreate this overload of attention, only this time the sweet is tainted by the bitter. Most of us, at some time, have given in to the temptation to see ourselves as the hero or heroine in tragic love films, and as the jilted lover in every sad love song out there.

Billboard have established the “Top 30 Breakup Songs” ever recorded . From their 30 we've selected 9 songs, and added one that we feel was sadly lacking, a song that's fast establishing itself as the breakup song of a generation. We've given the songs our own order (the original list ranked the songs by their popularity on the Billboard, while we're ranking by tragedy factor) but all but one of the songs presented here are from that list.  How did we whittle it down to 10? Well, “I Heard It Through the Grapevine,” for example, though most definitely about a broken relationship, has a beat that’s just a little too upbeat to be truly tragic. Same for “The Sign” by Ace of Base  - also included on Billboard's list - which is positively danceable! And though an incredibly sad sort of a song, the Police’s “Every Breath You Take” has been described by Sting as a dark piece about when the jilted lover becomes an obsessive stalker-type… so we didn’t include that one.

What are the most tragic breakup songs of all time? Hopefully, if you listen to any of these anytime soon, it won't be because you're currently one of the tragic heartbroken masses who find sympathetic solace in these heartrending songs.

10 I Will Always Love You:  Whitney Houston


We will always love Whitney Houston! If you’re old enough, you’ll remember the serious overplay this 1992 song got after the release of the film The Bodyguard. Still, this song has proven itself over the past 22 years, and it has become a timeless classic. Houston’s spectacular singing truly emphasizes the tragic with a lilt of the voice that cannot be achieved by just anyone with the mechanics of good vocal chords. The song’s lyrics, too, are extremely moving: “If I should stay / I would only be in your way / So I'll go, but I know / I'll think of you every step of the way / And I will always love you…”

9 Need You Now:  Lady Antebellum

This 2010 song is so lovely it makes drunk dialling an old lover at 2am sound less pathetic than it actually is. Most of us can relate to thinking of someone who doesn’t want to be thought of by their ex anymore, and certainly doesn’t want to be phoned in the middle of the night! That this song has both a male and female singing about an ended relationship makes it especially poignant. “And I wonder if I ever cross your mind? / For me it happens all the time.” Those words sung with their particular melody sums up perfectly a quintessential sorrow universal to jilted lovers everywhere.

8 Nothing Compares 2 U:  Sinead O’Connor


This song written by Prince and made world-renowned by Irish singer Sinead O'Connor was released in 1990. The person “speaking” in the song has been literally counting time passing: “It's been seven hours and fifteen days / Since u took your love away.” Besides a haunting tune filled with real angst, Prince’s lyrics describe well the hopeless attempt to forget by keeping busy, filling your schedule with social events, revelling (or trying to) in being able to go wherever and do whatever you want. “I can eat my dinner in a fancy restaurant / But nothing / I said nothing can take away these blues / ’Cause nothing compares / Nothing compares 2 u.”

7 Apologize:  Timbaland feat. One Republic


One Republic’s lead singer makes gals swoon, no doubt thinking that if they had been the subject of this 2007 song, it’d be a different tune. Here, it was the girl who screwed up, big time. She messed up so badly that the song’s “hero” will not let his lover come back, no matter what she says or how she says it. All this, even though he’s still, by his own admission, “ten feet off the ground” for her. Ryan Tedder sings: “You tell me that you need me / Then you go and cut me down / But wait... / You tell me that you're sorry / Didn't think I'd turn around / And say... / That it's too late to apologize / It's too late... / I said it's too late to apologize / It's too late…”  WE wouldn’t do you that way, Ryan!

6 End of the Road:  Boyz II Men


“Said we'd be forever / Said it'd never die / How could you love me and leave me / And never say goodbye? / When I can't sleep at night without holding you tight / Girl, each time I try I just break down and cry / Pain in my head, oh I'd rather be dead / Spinnin' around and around…” This song released in 1991 really has that early 90s sound, along with popular boy-band stylings that haven't gone out of date. The lyrics illustrate well how night time makes all troubles seem bigger, especially rejection and heartbreak. The heart-wrenching song’s cuckolded lover is deep in the throes of the night time blues: “Although we've come to the end of the road / Still I can't let go.”

5 Smoke Gets In Your Eyes:   The Platters


If you feel like being sad, this song, over a half century old, will more than fit the bill. Written for a 1933 musical, it was made popular in the late 50s by The Platters, whose then lead-singer Tony Williams sang the song into a Billboard No. 1 position. Separated from Timbaland’s “Apologize” by 74 years, the words express the same cause for breakup: female betrayal. “They / Asked me how I knew / My true love was true… / They / Said someday you'll find / All who love are blind / When your heart's on fire / You must realize / Smoke gets in your eyes.” A modern translation of the renowned line might be a lot less pretty, with the phrase: “She sure blew smoke up your ass.”

4 It Must Have Been Love:   Roxette


“Lay a whisper on my pillow / Leave the winter on the ground / I wake up lonely / This air of silence in the bedroom / and all around / Touch me now, I close my eyes and dream away / It must have been love, but it's over now / It must have been good, but I lost it somehow.” This song, used on the soundtrack for the Julia Roberts movie Pretty Woman, is nothing if not bereft: of love, but more importantly of hope, a sign of a truly great, tragic breakup song. What makes this 1992 song really bleak is the way the singer takes the blame for losing love, a stance most who are heartbroken will take, even though it takes two to start and end a thing.

3 Un-Break My Heart:   Toni Braxton


What a tune! Written by Diane Warren of the Songwriter’s Hall of Fame, Braxton at first refused to sing the ballad, but was finally convinced. It was released on her 1996 album Secrets. In “Un-Break My Heart” the listener is convinced the singer’s heart truly is broken; Braxton captures perfectly the sound of immense loss with her tragic delivery of an unforgettable chorus: “Un-break my heart / Say you'll love me again / Undo this hurt you caused / When you walked out the door / And walked out of my life / Un-cry these tears / I cried so many nights / Un-break my heart / My heart…”

2 We Belong Together:   Mariah Carey


This 2005 tune stayed at Billboard’s No. 1 for 14 weeks in a row, making it the second-longest running No. 1 hit, behind Carey’s own 1995 release, “One Sweet Day.” This was a feat for the singer, who had seen her popularity greatly decline in the beginning of the 21st century. With “We Belong Together” she had the comeback she so badly needed. Is it heartbreak that gets us where it counts? “I lost a part of me / When you left boy can't you see / Boy come back, baby, please / 'Cause we belong together / Who am I gonna lean on / When the times get rough / Who's gon' talk to me / 'Til the sun comes up / Who's gon' take your place?” Ouch….

1 Adele - Someone Like You

"Don't forget me, I beg / I remember you said, 'Sometimes it lasts in love but sometimes it hurts instead'"This one didn't land a place on Billboard's Top 30 Break Up songs, as they listed instead Adele's 'Rolling In The Deep'. But since its 2011 release, this number 1 song has been defining heartbreak for millions the world over. This break up song is unique in that it speaks to the painful nostalgia of losing a loved one without portraying selfish or self-indulgent emotions. Its purely regretful tone is testament to a love that endured long after the other party had moved on. Adele's now world-famous, iconic performance of this song at the Brit Awards in 2011 saw the talented singer break down in tears on stage - a public display of emotion that represented just how intimately real the song is. In the week following this performance, the song lept from number 16 to number 1 on the American charts.

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