Unlucky in Love: 13 Songs for Valentine’s Day Haters

Evidence of the staying power of the title sentiment: Since 1960, this song has been recorded by an astonishing array of talent, including the Everly Brothers, Roy Orbison, Cher, Joan Jett, Heart and even Keith Richards mellowly harmonizing with Norah Jones.  But the 1975 hit version by Nazareth makes the grade because you really believe singer Dan McCafferty is in pain.

The Smiths recorded plenty of forlorn songs (Morrissey could always find reasons to be miserable beyond the state of his romantic life), but their last single, in 1987, stripped down their music to its loneliest core: “Last night I dreamt that somebody loved me / No hope, no harm, just another false alarm.”

Jackson's most sorrowful ballad (from 1979's Off the Wall): By the end, his voice cracks, as he's unable to find any solace from the song or his turquoise sweater. Ignore the sneaking suspicion that he's singing to a pet (a pony? a giraffe?), and feel the intensity of his raw emotion.

Pink's tempestuous relationship with her husband, motocross rider Carey Hart, has provided her with endless fuel for her music. This 2008 song hit Number One worldwide because it took the real pain of the couple's split (check out the heartbreaking "you weren't there" bridge) and transforms it into the things people do to get over a breakup: Drinking, fighting, showing off their rock-star moves.

The original version of this song (from Elvis Costello‘s 1986 album Blood and Chocolate) is an epic testament to jealousy over a former lover’s new partner – obsessing over it may be cold comfort, but at least that’s a form of comfort. This clip, from a 2006 VH1 tribute to Costello, has him on guitar and Apple on vocals and she metabolizes every molecule of the song’s poisoned atmosphere.

If you're getting serious about wallowing in the pain of a breakup, some genres of music will pay off more than others. And when you're really down, you want the blues. They don't get much more brutal than this 1956 single from Howlin' Wolf. "I asked her for water," he moans. The punchline: "She brought me gasoline."

In a brilliant career carefully managed for public consumption, this 2002 song was the moment when Timberlake exposed his private life. This jittery ballad is a kiss-off for an unfaithful former lover that everyone knew was Timberlake's ex Britney Spears (represented in the video by a lookalike). "The damage is done, so I guess I should be leaving," Timberlake sang. A credo for anyone trying to regain their pride after they get betrayed.

With a new-wave snarl and an ace pub-rock band, Joe Jackson recorded a debut album (1979's Look Sharp!) that was mostly about the discontents of being unwillingly single. This track places the blame where it obviously belongs: With his friends who are already paired off. (Years later, Helen Fielding's Bridget Jones would call them "smug marrieds.")

The brutal mathematics of a breakup: “It’s been seven hours and 15 days since you took your love away from me.” This song, written by Prince for a forgotten 1985 side project (The Family), was revived in 1990 by O’Connor and producer Nellee Hooper, and turned into a beautiful, unflinching embrace of sorrow.

The greatest concept album ever about divorce is Marvin Gaye's 1978 Here, My Dear. In a settlement with his ex-wife (the recently deceased Anna Gordy), he agreed to give her half the royalties from an album, and then proceeded to make a double album about the dissolution of their relationship. This rueful song is the centerpiece.

Entire country music careers have been built on the power of breakup songs and this 2009 ballad from Keith Urban, where he bids farewell to an unfaithful lover (and her records) is one of the latest links in a long chain. Urban’s voice perfectly captures the mix of sorrow and pleasure that the end of a relationship can bring.

One of the most brutal breakup songs ever, from the 2010 masterpiece My Beautiful Dark Twisted Fantasy. West tries to work out his anger towards his ex (Amber Rose, now married to Wiz Khalifa), but the more venom he directs towards her, the more obvious it becomes he can’t figure out how his own heart works. A song for anyone going through an angry split. (This version ends before the raw, NSFW monologue by Chris Rock.)

Back in 1980, the J. Geils Band knew that sometimes love just makes you want to go into a dirty alley in the winter and beat on a drum with a frozen fish.