10. Drake – "Marvin's Room"

Drake has helped usher in a particularly sensitive strain of rap music, and one of his calling card cuts that best demonstrates this blend of downtempo R&B and introspective words is "Marvin's Room". The candid offering features Drake's drunken rambling to an ex he's not quite over - he's almost begging after a night out, lonely and inebriated and slurring his way through pleas of desperation. It's a humbling look on one of the world's biggest musicians.

Bonus fact: legend has it that "Marvin's Room" got its name from the studio it was recorded in - a studio once owned by Marvin Gaye. LD

Key Line: "Talk to me, please, don't have much to believe in / I need you right now, are you down to listen to me?"

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9. Wilco – "I Am Trying To Break Your Heart"

The story of Yankee Hotel Foxtrot, Wilco’s landmark fourth album, is the stuff of modern rock legend. It was recorded entirely in Wilco’s Chicago-based studio The Loft and bankrolled by the Warner-owned Reprise Records, but upon delivery the label refused to release it claiming there were 'no songs fit for radio' and ordering Jeff Tweedy - the band’s principal songwriter - to change it. After countless arguments, the label dropped the band - giving them full rights to the record - and, after releasing the album as a free stream via their website (the first of its kind), the band signed with Nonesuch - a label ironically also owned by Warner who ended up paying for the record twice! All this (and more) was documented in Sam Jones’ 2002 documentary I Am Trying To Break Your Heart which leads us perfectly into the song in question.

The album’s opener sees Tweedy & Co. build upon a simple folk tune and deconstruct its very essence right before the listeners’ eyes (ears). A song about holding on to the past whilst suffocating a partner with insecurities and that, no matter how hard you try and grasp onto a former love - when it’s over, there’s absolutely nothing you can do about its finality. It’s all gut-wrenching stuff, furthermore accented by Glen Kotche’s fragmented drum patterns and the late, great Jay Bennett’s sonic textures. Still a staple of Wilco’s live show, "I Am Trying To Break Your Heart" is a modern masterpiece and the perfect opener to an album that was initially kicked to the curb like an unwanted lover and went on to be the band’s biggest sellling to date. RT

Key Line: "I'd always thought that if I held you tightly / you'd always love me like you did back then..."

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8. Elliott Smith – "Oh Well, OK"

The late singer/songwriter had an uncanny knack for conveying darker emotions, and "Oh Well, OK" might just be his most heartbreaking venture. It has Smith singing about sifting through old photos and trying to figure out just what went wrong in a relationship - he's trying to paper over the cracks and pretend it doesn't bother him anymore, but he's not fooling anyone. It's a resonant track - it's not necessarily something that galvanises torrents of tears in the aftermath of a messy split, but rather a tender ode that soundtracks those private twinges of pain long after the parting of ways. It's the kind of song that resharpens dull memories. LD

Key Line: "Here's the silhouette, the face, always turned away / the bleeding colour gone to black, dying like a day..."

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7. LCD Soundsystem – "Someone Great"

On the face of it this is pretty standard breakup jam - albeit a mindblowing jam that could've only come from the brains of LCD. Behind the twinkling synths and chimes are fading memories and regrets from James Murphy, who sounds as desperate and despairing as ever... but this isn't about a lost partner. This 'breakup', if you can technically call it that, more an anthem for loss in general - and although Murphy's been deliberately quiet about the inspiration, some have suggested it stems from the death of Dr. George Kamen, who the album which "Someone Great" features on (Sound Of Silver) is dedicated to.

"I think about songs in terms of them just being objects and not things that are about something else," Murphy told The Quietus when asked about song meanings. "I just think it’s unnecessary because it’s personal. Songs are songs and to reduce them is to waste them. If I wanted to make something about something I would write an essay." LD

Key Line: "To tell the truth I saw it coming / the way you were breathing / but nothing can prepare you for it / the voice on the other end..."

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6. Beyoncé – "Irreplaceable"

Is this a sincere kiss-off? Is it Queen B just putting on a brave face? Either way it's a mighty show of strength and independence, and it's arguably the song that put Beyoncé's name on the world's lips. Despite the rather maudlin melodies, the amount of bite in the lyrics is almost palpable - the title makes you think it's a ballad about a partner you can't replace, but it's actually the complete opposite.

Bey's honesty isn't actually key here, as "Irreplaceable" has taken on a life of its own as a late-stage breakup anthem. Speaking to MTV, she revealed: "I've had so many people come up to me in tears, saying, 'I experienced my first breakup. If it wasn't for the song, I wouldn't be strong enough to not call. I wouldn't know how much I'm worth.' I'm happy to be a part of that." LD

Key Line: "Baby I won't shed a tear for you / I won't lose a wink of sleep / 'cause the truth of the matter is / replacing you is so easy..."

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5. Pet Shop Boys – "Always On My Mind"

This is a 20th-century country/western mainstay with versions by Willie Nelson, Gwen McCrae, John Wesley Ryles, Brenda Lee, and The King himself - Elvis Presley - but the most popular and the best (yep, we said it) version comes from '80s synthpop stalwarts the Pet Shop Boys. It's simultaneously euphoric and heart-stoppingly sad, with the pair maxing out the levels of bittersweetness. A sad banger to end all sad bangers.

The duo originally created their rendition for Love Me Tender, a UK TV special paying tribute to Presley on the 10th anniversary of his death, but it proved so popular that they gave it a proper release. 30 years on from that, it's held aloft as one of the greatest cover songs ever. Not bad, eh? LD

Key Line: "If I made you feel second best / I'm so sorry I was blind / you were always on my mind..."

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4. Solange – "Losing You"

After a lengthy period of quiet, Solange returned to the world of music with "Losing You", a solid-gold track produced by Blood Orange/Dev Hynes and of Montreal's multi-instrumentalist Kevin Barnes. Solange says that it's "eclectic with '80s references and African percussion influences", and although she's the voice that carries the sentiments, it's not necessarily about anyone in her life.

In an interview with The FADER, they point out that "Losing You" was a song first written by Hynes about an ex-girlfriend (the same ex-girlfriend that Sky Ferreira collab "Everything Is Embarrassing" is about). Unfortunately there was some disagreement along the way about who deserved what credit on "Losing You" and it all came to a bit of a head and they fell out in spectacular fashion. Kinda adds another layer of sadness to the track, in a way. LD

Key Line: "I don’t know why I fight it, clearly we are through / tell me the truth boy, am I losing you for good?"

Get it from Amazon or iTunes.

3. Lauryn Hill – "Ex-Factor"

The former Fugees' member's solo debut The Miseducation Of Lauryn Hill is stuffed with jewels, but few capture the intensity of a breakup quite like "Ex-Factor" (though "I Used to Love Him" comes close). The self-produced and self-written track, which incorporates parts of "Can It Be All So Simple" by Wu-Tang Clan, is thought to be centred on her fiery relationship with former bandmate Wyclef Jean - the same relationship which was going on behind Jean's wife's back and is rumoured to have split the Fugees in the first place.

"Ex-Factor" is crammed so full of emotions of all shades that by the end it all just boils over: it's an anthem of frustration, desperation, anger, love, and gradual realisation. Some things just don't work out, no matter how brightly the flame burns. LD

Key Line: "No matter how I think we grow / you always seem to let me know / it ain't workin', It ain't workin'..."

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2. Leonard Cohen – "Hey, That's No Way To Say Goodbye"

Cohen's 1967 track (actually released first by Judy Collins one month earlier), like many of his works, has been taken and strewn about the zeitgeist by a great number of artists. Few come close to the raw power and maturity of the original however, which is level-headed and sincere when it could all-too-easily be flying off the handle.

"This song arises from an over-used bed in the Penn Terminal Hotel in 1966," Cohen writes in the 2009 Greatest Hits compilation textbook. "The room is too hot. I can’t open the windows. I am in the midst of a bitter quarrel with a blonde woman. The song is half-written in pencil but it protects us as we manoeuvre, each of us, for unconditional victory. I am in the wrong room. I am with the wrong woman." LD

Key Line: "You know my love goes with you as your love stays with me / it's just the way it changes, like the shoreline and the sea..."

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1. Bob Dylan – "If You See Her, Say Hello"

Recorded during an abruptly organised session in Minnesota on 30 December 1974 and released just 21 days later, "If You See Her, Say Hello" is perhaps the most brutal of all of Blood On The Tracks' 10 songs - an album that that zones in on Dylan’s estranged relationship with his then-wife Sara Lownds.

With lyrics often shrouded in mystery, riddles, and psychedelic imagery - Blood On The Tracks saw Bob Dylan at his most autobiographical and honest yet. Immediately hailed as a classic, the attention and album’s popularity often miffed Dylan. He once told Mary Travers (of '60s folk darlings Peter, Paul and Mary): "A lot of people tell me they enjoy that album. It's hard for me to relate to that. I mean... people enjoying that type of pain, you know?"

Whilst "Tangled Up In Blue" and "Shelter From The Storm" are often seen as the album's stand-outs, it's "If You See Her Say Hello" that takes Blood On The Tracks’ theme and rips it open for all to see. It's a song about the pains of a lost love and the wounds that entail, with Dylan’s voice - draped over stripped-back open-chords and lightly picked bass - almost quivering in its sadness. But Dylan is never resenting the song’s subject, and the pay-off line ("Tell her she can look me up if she's got the time..."), delivered in a forgiving tone, makes the whole thing even more heartbreaking. RT

Key Line: "Though our separation, it pierced me to the heart / she still lives inside of me, we've never been apart..."

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Writers: Larry Day, Aaron Powell, Rich Thane, and Lauren J Down.