9 Songs Inspired by Real Heartbreak

Heartbreak sucks, but it’s also responsible for some of our favorite songs. In the case of Robin Thicke, it inspired an entire album. Thicke’s latest effort, titled Paula, seems likeone valiant attempt to mend his broken heart and win back his estranged wife, Paula Patton. In fact, the first single off the album is titled “Get Her Back.” We have no idea whether his grand gesture will work, but it has prompted us to gather up as many real-deal, heartbreak-inspired songs as we could:

1. Björk – “Possibly Maybe”


The mesmeric qualities of “Possibly Maybe” always made me feel like I was in some musical fantasy land. That is, until I started picking up on lyrics like “I suck my tongue in remembrance of you.” Technically, I still feel like I’m in some musical fantasy land, but now it’s just a little more sinister. Björk stated that “Possibly Maybe” was the “first unhappy song [she] wrote” and subsequently felt “ashamed writing a song that was not about giving hope.” The song was reportedly dedicated to her break up with Stéphane Sednaoui, who, weirdly, directed the song’s video. Hmm. . .

2. Carly Simon – “You’re So Vain”


There’s been a lot of speculation about who this song is really about—so much speculation, in fact, I don’t even think Carly Simon knows. Throughout the years, she’s alluded to the subjects being Mick Jagger, Warren Beatty, David Geffen and/or an amalgamation of all the vain men she’s come across. Either way, she’s left us with an iconic eff you anthem that we’re all grateful for.

3. Adele – “Chasing Pavements”

This list wouldn’t be complete without at least one song from Adele. I mean really, almost any song from her 21 album could be on this list, but I thought “Chasing Pavements” had the most entertaining history behind it. “Chasing Pavements” was inspired by Adele’s cheating ex. In an interview with , Adele said:


4. Nick Cave – “Into My Arms”

In Toby Creswell’s book, 1001 Songs: The Greatest Songs of All Time and the Artists, Stories and Secrets Behind Them, Creswell claims that “Into My Arms” was inspired by Nick Cave’s relationships with both Viviane Caneiro and PJ Harvey. Interestingly enough, PJ Harvey wrote a heartbreaking song with Thom Yorke called “This Mess We’re In,” but no word on who it’s about.

5. Justin Timberlake – “Cry Me A River”

Remember how much speculation surrounded this number? Even though Justin refused to comment on who the song was about, his very public split with Britney Spears certainly fueled a lot of rumors. Oh yeah, and putting a Britney Spears look-alike in the video didn’t exactly help either. Nine years after the song’s release, Justin came close to ‘fessing up about the Britney connection, saying:

As if we needed any more confirmation, Britney released “Everytime” as a musical response to “Cry Me a River.”

6. Aimee Mann – “Just Like Anyone”

Aimee Mann wrote this song as a tribute to the late Jeff Buckley. Although the two weren’t close, she recalls an experience when the two of them were together at a bar:

Long after their meeting at the bar, Aimee claims that she received a voice mail from Buckley, saying, “I just realized what you were trying to tell me that night”. When she finally had a moment to call his updated number, he was already gone. Buckley drowned in Wolf River Harbor in Memphis, Tennessee.

7. No Doubt – “Ex-Girlfriend”

Like Adele, Gwen Stefani has a collection of songs that were inspired by break-ups. One of those songs, interestingly enough, is dedicated to her now-husband, Gavin Rossdale. Apparently, the lyrics to “Ex-Girlfriend” (“You say you’re gonna burn before you mellow/ I will be the one to burn you“) are a direct response to Bush’s song, “Dead Meat,” where Gavin sings, “I’m doing you in tomorrow/ I’ll burn before I mellow.” Ouch. That sounds like a rough patch. Who would’ve guessed these two would end up married?

8. Taylor Swift – “Dear John”


Well, here’s one we won’t have to speculate on. Swift wrote “Dear John” following her breakup with John Mayer, and Mayer was not amused. He told Rolling Stone:

Aah, the power of music.

9. Alanis Morissette – “You Oughta Know”

Although Morissette has never officially revealed the subject of the song, comedian Dave Coulier took full responsibility. Despite going on the record three times to insist the song was about him, Coulier just recently revealed that he did it for the laughs:

Hey, I wouldn’t put it past him. Let’s just write this one off as a Carly Simon situation.

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