It's Okay To Cry: The 20 Saddest Love Songs Of All Time
Heartache weaves its way through countless songs by countless artists - there's lots to sift through but some have the power to stay with you forever, and these do. These are the 20 saddest love songs of all time.
A pyrrhic victory? It's awfully bittersweet to have created something so beautiful out of something so traumatic, but these 20 artists have done it - from unique heartbreak to universal loss, there's something for everyone to bawl along to. Better grab the tissues before you start...
20
Toni Braxton – "Un-Break My Heart"
Toni Braxton's megahit was penned by the award-winning Diane Warren, a powerhouse in the world of power ballads with numerous credits on songs made massive by Whitney Houston, Celine Dion, Meat Loaf, Cher, and lots more. With a pedigree like that and a voice like Braxton's, how could this not be a wild success? Well it almost wasn't.
"Toni hated the song... she didn't want to do it," Warren revealed. Eventually her label boss L.A. Reid convinced her to record it - and the results weren't too bad in the end, were they? - but Braxton was still unconvinced. It wasn't that she disliked the actual song, but just that she didn't really want to make another "heartbreak track". LD
Key Line: "Un-cry these tears / I cried so many nights / un-break my heart, my heart..."
19
No Doubt – "Don't Speak"
This crushing banger, co-written by siblings Eric and Gwen Stefani, was fuelled by the No Doubt frontwoman's breakup with bandmate Tony Kanal. It featured on the group's third record Tragic Kingdom, reaching the top of the charts across the globe and propelling them to superstardom - but it all stemmed from heartache. Originally a swoonier love ditty with different lyrics (a demo version exists in certain circles), the breakup between Gwen and Kanal meant that "Don't Speak" took a different route entirely.
"It used to be more upbeat, more of a '70s rock-type thing," Gwen said to The Independent in 2010. "[When] Tony and I broke up... it turned into a sad song." LD
Key Line: "Our memories, they can be inviting / but some are altogether mighty frightening..."
18
Ryan Adams – "Do You Still Love Me?"
Adams has been pretty candid about the inner workings of his landmark record Prisoner. It's inspired heavily by his divorce from singer/actress Mandy Moore, and looks in depth at the circumstances before, during, and after their breakup - it's a candid opus from one of rock's most important voices of the past 20 years, and "Do You Still Love Me?" sits front and centre with searing riffs and an emotional honesty that resonates from start to end.
"I started writing this record while I was going through a very public divorce, which is a humiliating and just a fucking horrible thing to go through no matter who you are," Adams told Japan Times in 2017. "To be me and to go through that the way that I did was destructive on a level that I can’t explain. So a lot of extra work went into keeping my chin up and remembering what I did and what I loved about who I was."
Despite that, Adams insists Prisoner isn't the result of despair... but quite the opposite: "This record was not born of sadness, and I was not crying. I was elated. Very stoned. And very free in those moments" LD
Key Line: "I been thinking about you, baby / been on my mind / why can't I feel your love? / heart must be blind..."
17
Taylor Swift – "Forever and Always"
Taylor Swift's reputation (ha) as a spurned lover precedes her, with breakup songs piled precariously high in her arsenal. Whether any of that is PR manoeuvres in the dark scarcely matters; Swift might be painted as the jiltedest of jilted parties, but she is, objectively, an absolute don when it comes to heartbreak anthems. There are countless tales set to music, particularly in her countrier days, and "Forever and Always" hits the rawest nerve with its roots in her chaotic uncoupling with Joe Jonas.
"It's about watching somebody fade away in a relationship," Swift told the LA Times in 2008. "They said they were going to be with you forever, that they loved you, and then something changed in the relationship and you don't know what it is, but you're watching them slowly drift. That emotion of rejection, for me, usually starts out sad and then gets mad. This song starts with this pretty melody that's easy to sing along with, then in the end... I'm basically screaming it because I'm so mad. I'm really proud of that."
For his part, Jonas has been a bit of a patronising ass, saying in 2009 that the song is "flattering... it's always nice to hear their side of the story." LD
Key Line: "So here's everything coming down to nothing / here's to silence that cuts me to the core..."
16
Sinéad O'Connor – "Nothing Compares 2U"
The Irish singer/songwriter's version of the Prince deep cut is a prescription-strength tearjerker; it's basically an onion in song form. "Nothing Compares 2U" is beautiful in its simplicity, with echoing percussion, the odd piano stab, and spaced-out strings backing O'Connor's perfect delivery - but it wasn't all peachy behind the scenes with The Purple One, who wasn't particularly happy that it was made without him.
"I made it without him," O'Connor told Norwegian radio station NRK a few years back. "I'd never met him. He summoned me to his house - and it's foolish to do this to an Irish woman - he said he didn't like me saying bad words in interviews. So I told him to fuck off. He got quite violent. I had to escape out of his house at five in the morning. He packed a bigger punch than mine." LD
Key Line: "It's been seven hours and 15 days / since you took your love away..."
15
Bon Iver – "Skinny Love"
Bon Iver's Justin Vernon struck emotional gold with "Skinny Love", the standout track on his album For Emma, Forever Ago. He's actually been quite candid on the meaning and the story behind it, and it's not strictly about former partner Christy Smith, who also played on For Emma....
"I’m not afraid to talk about ['Skinny Love'], but how do you guarantee it’s accurate?" Vernon told Pitchfork in 2011. "To say that 'Skinny Love' is about Christy would not be entirely accurate. We dated and she’s an incredibly important person that I lived with for a long time, but it’s about that time in a relationship that I was going through; you’re in a relationship because you need help, but that’s not necessarily why you should be in a relationship. And that’s skinny. It doesn’t have weight. Skinny love doesn’t have a chance because it’s not nourished." LD
Key Line: "Staring at the sink of blood and crushed veneer / I tell my love to wreck it all / cut out all the ropes and let me fall..."
14
The Magnetic Fields – "I Don’t Want To Get Over You"
"There’s plenty more fish in the sea... time heals all wounds… when one door closes, another one opens..." You know what? Shut up! Sometimes, we just want to wallow in our post-breakup misery. No song expresses that sentiment quite like “I Don’t Want To Get Over You”. Stephen Merritt’s voice, so deep and forlorn, murmuring in turn with the beating of a broken heart - almost guttural in its delivery of the lyrics. LJD
Key Line: "'Cause I don't want to get over love / I could listen to my therapist / pretend you don't exist / and not have to dream of what I dream of...”
13
Imogen Heap – "Hide and Seek"
It's by far Imogen Heap's most recognisable song - that might be 'cause of Jason Derulo, Saturday Night Live, or The O.C. - but it's not lost its punch. Heap's vocoder-assisted a cappella(ish) anthem is a perennial tearjerker that Heap's reluctant to dive deep into the meaning of - it's supposedly written from the point of view of a child stuck in the middle of a messy divorce, torn between two parents while the family home falls apart.
Heap's performance of "Hide and Seek" at the One Love concert in Manchester is particularly poignant (although for a different reason). LD
Key Line: "Oily marks appear on walls / where pleasure moments hung before..."
12
Joy Division – "Love Will Tear Us Apart"
A grieving angel on the Ribaudo family tomb sculpted by Onorato Toso in 1910 became the powerful image used by Joy Division for the cover of perhaps their greatest song, one that has become synonymous with melancholy and sorrow. Recorded mere months before frontman Ian Curtis’ death, “Love Will Tear Us Apart” is an insightful look at the singer’s troubled marriage to Deborah Curtis and his own tortured mind.
Joy Division will forever be remembered as architects of tuneful lamentation and minimalist misery, making them the perfect band to have a good old sob to. AP
Key Line: "You cry out in your sleep / all my failings exposed / and there's a taste in my mouth / as desperation takes hold..."
11
Amy Winehouse – "Back To Black"
A heartbreaker of the highest calibre. It might be surprising to see this as one of Winehouse's most famous and radio-ready works, given the blatant nods to drug use and frankly harrowing conclusions to the story; some believe the 'black' she returns to isn't a life of sadness and loneliness, but heroin - black being a common street name for the drug to which the soul legend had a troubled relationship with. Regardless of that reading, this twisted tale of unrequited love (inspired by her turbulent relationship with Blake Fielder-Civil) is one that strikes hard and deep due to the sheer veracity of the lyrics. LD
Key Line: "I loved you much, it's not enough / you love blow / and I love puff..."
Get the Best Fit take on the week in music direct to your inbox every Friday
Emily Burns
Die Happy
Halsey
The Great Impersonator
Katie Gavin
What A Relief
