Heartbreak Station: 5 Great Breakup Songs

by Mark MacDonald, Staff Writer –

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“Love is a battlefield,” wrote Pat Benatar, and it’s true that most of us, at some point in our lives, will go through a breakup. At these moments, we gravitate to the music inspired by the same emotions we feel, be them sorrow, triumph, tranquility or resentment. Here’s a list of 5 of the best breakup songs.

  1. Don’t Speak – No Doubt
No Doubt - Don't Speak single cover

No Doubt – “Don’t Speak” single cover

The third single released from No Doubt’s third studio album, Tragic Kingdom (1996) “Don’t Speak” was written by Gwen Stefani shortly after her bandmate, Tony Kanal, ended their seven-year relationship. The song was nominated for two Grammy awards and was the band’s most successful international single, topping the charts in the UK, New Zealand, Canada and Australia. The lyrics portray sorrow and loss at the onset of a breakup, with the signature line: “Don’t speak, I know just what you’re saying, so please stop explaining, don’t tell me ‘cause it hurts” setting the tone. Though Stefani may have been heartbroken at the time, she later became a massively successful solo artist (winning a Grammy) started a clothing line, was a judge on The Voice and has amassed an estimated net worth of $100 million.

  1. I’m Going Down – Bruce Springsteen
Bruce Springsteen - "I'm Going Down" single cover

Bruce Springsteen – “I’m Going Down” single cover

Recorded at the Power Station music studio in 1982 and featured on his 1985 album Born in the USA, the single “I’m Going Down” is an energetic song about diminishing intimacy in a romantic relationship, and the sense that a breakup is soon to occur. Springsteen paints a picture of a man who sees the end of the relationship coming, despite wishing it wasn’t so. Lines like “I pull you close now baby but when we kiss I can feel a doubt” spell it out: it’s over; time to face the music.

  1. Let it Die – Feist
Feist - "Let it Die" single cover

Feist – “Let it Die” single cover




One of the most popular Canadian acts, Feist launched her solo career in 1999 with the album Monarch, followed by her second solo album Let it Die in 2004. The album won Juno awards for Best New Artist and Best Alternative Album and featured the hit single of the same name. Let it Die speaks to the regret of entering into a relationship that, in hindsight, should have never been started. Lines like “We don’t see eye to eye, or hear ear to ear,” and “Now I know what I don’t want, I learned that with you,” strike home the idea that some relationships are full-on mistakes. In these cases, it’s best to end it sooner rather than later and, as Leslie Feist writes, “Let it die.”

  1. Back to Black – Amy Winehouse
Amy Winehouse's Back in Black

Amy Winehouse’s Back in Black

Inspired by Amy Winehouse’s relationship with Black Fielder-Civil (who left Amy for an ex-girlfriend) the hit song “Back to Black” was featured on the late artist’s final album of the same name and is considered to be one of her signature songs. Many consider the term “back to black” as referring to a return to heroin, as “black” is a common street name for the narcotic in Los Angeles. The song is blunt and frank, and though the lyrics express feelings of hurt and bitterness, they also speak to strength and acceptance, with lines like “me and my head high, and my tears dry, get on without my guy.” The song is an infectious combination of old school soul music, R&B and the sounds of vintage girl groups from the 1960s and includes the brilliant lyric “we only said goodbye in words.” A great track from an artist who tragically left us far too soon.

  1. Don’t Think Twice, It’s All right – Bob Dylan
"Don't Think Twice it's Alright" from Dylan's second full length LP, The Freewheelin' Bob Dylan

“Don’t Think Twice it’s Alright” from Dylan’s second full length LP, The Freewheelin’ Bob Dylan

Sometimes breakups aren’t the worst thing in the world. In fact, sometimes it’s quite all right, or at least you can convince yourself it is. Bob Dylan’s 1963 single portrays just that kind of feeling. “Don’t Think Twice, It’s All Right” was written by Dylan in 1962 and released as part of his 1963 album The Freewheelin’ Bob Dylan. Many aspects of the song, including the melody and some of the lyrics, are based on the public domain song “Who’s Gonna Buy Your Chickens When I’m Gone,” taught to Dylan by folksinger Paul Clayton, who himself used it. In typical Bob Dylan fashion, the lyrics are rich, poetic, and filled with folk undertones – with references to roosters and roads and the like. Lines like “I gave her my heart but she wanted my soul” and “Goodbye is too good a word, so we’ll just say farewell” reflect a muted sense of loss coupled with a general sense of closure and acceptance. My personal favorite breakup song of all time.