10 of the Creepiest Pop Songs of All Time

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Yes, it’s Halloween, and yes, that means that we’ve put together a Halloween-themed list. However, instead of rehashing “Thriller” and various Alice Cooper and Misfits tracks, we thought we’d go for some genuinely disturbing songs – specifically, 10 of the creepiest (as in, most genuinely unsettling) pop songs ever recorded. Obsessiveness, violence, car crashes, questionable sexual proclivities and an R&B singer with an unwanted erection… they’re all here. With deceptively pretty melodies.

The Police – “Every Breath You Take”

“Every Breath You Take” is music’s most famous tale of obsession — a fact that hip-hop übertwat P. Diddy missed entirely when he ripped off this song for his ghastly saccharine Notorious BIG tribute. Sting’s lyric here is downright frightening: “Every breath you take, every move you make, I’ll be watching you.” Um… people get arrested for that kind of thing.

Portishead – “All Mine”

Beth Gibbons also sounds decidedly scary at times, and never more so than on this track. “All Mine” is an evocation of how the desire to be loved can become a burning, all-consuming need for possession: “Tethered and tied,” she coos to the object of her “affection,” “There’s nowhere to hide from me…”

Michael Jackson – “Break of Dawn”

Declarations of Herculean sexual prowess are nothing new, but they’re infinitely more disturbing when it’s Michael Jackson making them. The idea of late-era Jackson “makin’ love all the way through the night” doesn’t really bear thinking about. The song just gets worse as it goes on: Soppy R&B? Flute? Lyrics like “Hold my hand / Feel the sweat”? Bird noises? We’re edging quietly toward the door.

Aaliyah – “Age Ain’t Nothing But A Number”

Pop music’s never been especially worried about whether its inspiration is underage or not (cf. Neil Diamond’s “Girl, You’ll be a Woman Soon” and Serge Gainsbourg’s infamous “Lemon Incest,” among many others). As such, it’s not even remotely surprising that this sultry tale of a younger girl overflowing with desire for an older man was written for a 14-year-old Aaliyah by… oh go on, guess. R Kelly? Correct.

George Michael – “Father Figure”

More disturbing pedophilic imagery here: “Put your tiny hand in mine,” sang George Michael, adding later that “I have had enough of crime.” At best this is ill-considered; at worst it’s all kinds of wrong. Either way, we’d suggest to budding songwriters that there are perhaps better metaphors than a parent/child relationship to use when you’re writing a love song.

Terry Jacks – “Seasons in the Sun”

Perhaps not so much creepy as desperately sad, this was a worldwide hit in 1974 despite being one of the most depressing songs ever committed to tape – originally recorded by the marvellous Jacques Brel, it was also later covered in characteristically limpid fashion by Irish wetbags Westlife. Beneath the pretty melody and chart-friendly production is a lyric that basically constitutes a musical suicide note. It makes for a kind of disturbing listening experience.

Next – “Too Close”

“Step back/You’re dancing kind of close/I feel a little poke coming through.” Listening to this is like getting groped on the subway.

The Crystals – “He Hit Me (It Felt Like a Kiss)”

Addressing the issue of domestic violence in music isn’t an inherently bad thing – there’s no subject that should automatically be off limits, after all – but getting female singers to sing male-penned lyrics that basically constitute an endorsement of violence as some sort of perverse expression of love… Well, that raises all sorts of moral questions, doesn’t it? To add to the whole air of wrongness, this song – recorded in 1962 by The Crystals – was produced by convicted murderer Phil Spector. (Grizzly Bear, incidentally, do a fantastic cover of this live.)

Grace Jones – “Warm Leatherette”

Jones’ version is probably the best-known interpretation of this song, originally recorded in 1978 by Mute Records founder Daniel Miller under the moniker The Normal. The lyrics were inspired by JG Ballard’s novel Crash, which would eventually adapted into the supremely perverse 1996 David Cronenberg film of the same name. As such, they describe the joys of car crash sex: “A tear of petrol/Is in your eye/The hand brake/Penetrates your thigh.” The fact that it’s a frankly terrifying six-foot Amazonian inviting you, “Let’s make love/Before we die/On warm leatherette” only makes the whole thing even more unnerving.

Aphex Twin – “Windowlicker”

The song isn’t particularly creepy per se – that video, however…