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The Six Most Depressing Love Songs OF All Time

Updated: Oct 8, 2020


Song; Ben

Who to blame; Michael Jackson

Song; BEN . Who to Blame; Michael Jackson

Chart Position US Number 1 UK Number 7

Heartbreak Rating 0/10. It's hard to get distraught over a piece of vermin.

Only the late Michael Jackson could make a love song about a rat and get away with it. Let’s face it, the king of pop has had a flair for the peculiar most his adult life, so it shouldn’t really have come as a surprise when he wrote an ode to a big dirty rat in the early seventies.

Multi-talented but a flawed genius, Jackson had been performing professionally for almost half a decade before topping the charts for the first time as a solo artist in 1972 with “Ben”. It would be used as the theme song to the film of the same name.

“Ben” was actually a sequel to the movie “Willard” – a 1971 low budget flick about a killer rat which starred 157 year old Ernest Borgnine (he’s been around since our Lord’s time, so he was probably only about 96 making this movie.)

The most disturbing thing about the king of pop however was not the numerous trails he faced, the skin pigmentation that changed him from black to white, or the fact he was a walking advertisement for the salvation army in the way he dressed, no, it’s the fact he never wrote a song as tender and loving about a woman the way he does about a filthy piece of vermin.

“Billy Jean” was a tramp, whilst “Dirty Diana” was, well, dirty.

Not a rat though, as the lyrics confirm.

When you’re starting a song by saying “Ben the two of us need look no more, we both found what we’ve been looking for”, you know the next 3 minutes are going to be just as disturbing.

Michael goes on to say Ben’s been running here and there, feeling he’s not wanted anywhere (and this surprises you Michael!)

“Most people want to turn you away, so I don’t listen to a word they say” (you will when rabies kicks in), and on and on until Jackson does everything but take out an engagement ring to make this creepy union complete.

Despite the disturbing lyrics and the possible union of man and rat, “Ben” was a huge hit for the then 14 year old American. Already a superstar in his family outfit, “Ben” topped the U.S. Billboard charts in August of 1972, whilst breaking the top ten in the U.K a month later.

It gave the Indiana born child protégé the first of 13 solo number 1 hits and would be the launching pad for a monumental solo career which would see him sell over 750 million records worldwide.

Not bad for a career which started by professing his undying love for a rat.

Useless Trivia No.962 – The art cover on the original pressings of “Ben” depicted Jackson above a crowd of people fleeing a large army of rats. Motown removed the cover as they reckoned it might scare off young listeners and their parents.

These days just a picture of Michael (minus the rats) would have the same effect. .


Song; All I wanna do is make love to you

Who to Blame; Heart

Chart Position; US Number 2 UK Number 8

Heartbreak Rating; 2/10. I'm pretty sure male rape is still illegal these days.

We guys always get a bad rep when it comes to relationships. Yes we can be cruel, insensitive and have the morals of an alley cat, but every now and then there comes women who’ll act just as insane as us and drag her good name through the dirt, all in the name of lust.

That woman is Ann Wilson.

One half the sisterly duo of Seattle soft rock band Heart, Ann used 1990’s “All I Wanna Do Is Make Love To You” to tell us it’s alright for women to half sex with hobo’s once he can actually get you pregnant.

The tune which tells of a one-night stand became one of Heart’s biggest selling singles yet it’s not exactly an anthem for girl power. Whilst the Spice Girls preached about taking control of your life, improved self esteem and empowering females everywhere, Heart’s little ditty involves extra-marital affairs, bastard children and vagrancy!

It’s raining cats & dogs on a lonely highway one night when a horny Ann Wilson spots a man on the side of the road “with no umbrella and no coat”. However because she’s broody and he’s a member of the opposite sex, she’s game – so offers him a ride (in more ways than one as it soon becomes apparent)

Now I’m sorry but any guy in the middle of nowhere with no umbrella or a coat is obviously a hobo so that was her first wrong move. The next couple of lines confirm that Ann’s mental state isn’t exactly top notch.

I didn’t ask him his name, that lonely boy in the rain

Fate tells me its right; this is love at first sight

Please don’t say it’s wrong; stay for the night

So having now established that Ann is indeed Glenn Close from Fatal Attraction, she offers the guy a seedy motel room and the ride of his life. Luckily the motel hasn’t a condom machine, and with the tramp not having a dime, and Ann obviating, the signs are ominous.

Cut to several years later, Ann’s still with her unsuspecting hubby and amazingly she runs into the hobo again (what where the chances) and he sees a set of baby blue eyes staring back at him.

Yep it’s the hobo’s offspring.

Ann then explains to him that “the one little thing he (the hubby) can’t give me is the one little thing that you can”, before slipping him a 50 dollar note and telling him to buy some clothes, a mug of soup and a room for the night.

Despite the strange message the song advocates, it didn’t do the veteran rock group any harm and Heart still perform to this very day – 35 years after they first formed in 1974.

Useless Trivia No 117; Statistics prove that at least 500 people are arrested for vagrancy ever month in Seattle, Washington. None of them have reportedly had sex with Ann Wilson.


Song ; Ruby (Don't Take Your Love To Town)

Who to Blame; Kenny Rogers

Heartbreak Rating; 4/10 Kenny should have shot her cheatin' ass (and an extra mark for the lyric "It's hard to love a man whose knees are bent)

Chart Position; US Number 6 UK Number 1

Songwriters cover a range of ways in which love is lost in relationships. The girl falls out of love; the guy cheats; the wife that can’t stand her hubby and runs off with the milkman. However country crooner Kenny Rogers covered the – crippled war veteran in wheelchair; can’t have sex so the bitch is leaving me – market all for himself with 1969’s – Ruby (Don’t Take Your Love to Town.)

The song, wrote about a real life situation by Mel Tillis and originally a hit for Johnny Darnell, sold more than 7 million copies worldwide, thanks to the Texas born singer’s special brand of heartbreak.

You see Kenny mustn’t be much of a catch because women keep leaving his sorry ass.

If it’s not “Lucille” – where she picked a fine time to leave him, or being the “Coward of the County”, Kenny’s not exactly a hit with the opposite sex. Throw in the fact he’s a degenerate gambler that doesn’t “know when to hold them, fold them, walk away or run” and it’s hard to find much sympathy for Mr. Rogers.

In this tune Kenny is a veteran of the Korean war who begs his lover not to get tarted up like a painted hussy and haul ass into town where a bunch of horny town-folk are waiting.

Although Kenny admits “it’s hard to love a man whose legs are bent” (you gotta love that lyric!) he still appeals to Ruby’s caring side and says he still needs company.

Ruby however needs something else!

Longing for the touch of a man who can caress, satisfy, and actually stand up, Ruby ignores her crippled cohort and heads to town.

It’s here Kenny finally snaps.

He’s heard the slamming of the door (like a hundred times before) and she’s left him with not even a smile. “If I could move I’d get my gun and put her in the ground” (them’s fightin’ words) as Rogers finally realises she’s just been holding out for the house and his disability pension.

Will Kenny wheel on into town and blow her good-for-nothing cheating ass away? Will he take a pitchfork and imbed it into both her and her husky young lover Cletus? Can he actually out manoeuvre the Paddy-wagon when it comes looking for him?

Well in a word - no. The next lyric pours cold water on those exciting possibilities.

“Oh Ruby, God sakes turn around”

And there you have it. After all the fighting talk, threats of shooting and possible disembowelment, Kenny just stays in his chair and begs one last time not to go.

Despite his pain, wheelchair, and cheating tramp, Rogers was soon comforted by the fact the song gave him his first UK number 1 and continues selling singles to present day even now at the age of 70.

And Kenny had the last laugh when you think of it. He’s a multi-millionaire singer while Ruby married Cletus, got divorced and now lives on a chicken ranch in Nevada.

Useless Trivia No.351 – Kenny’s backing band were “The First Edition” who’s biggest hit was the quirky titled “Just Popped In (To See What Condition My Condition Was In.)


Song; Sylvia's Mother

Who to Blame ; Dr Hook & the Medicine Show

Heartbreak Rating 6/10. If you've just broken a girls heart the last thing you should do is call her mother!

Chart Position; US Number 5 UK Number 2

There are many love songs which bring a tear to an eye. Many whose lyrical content actually tell the true story of a long lost love or personal tragedy.

Then there’s those that whinge.

And Christ this is one of them.

Despite being a massive trans-Atlantic hit and giving New Jersey soft rock/country outfit Dr Hook & The Medicine Show their biggest single to date, I can’t have any sympathy for a man who spends about twenty euro on the phone professing his love to his lover’s mom whilst Sylvia is down at the local train station about to head out of his life forever.

Dennis Locorriere isn’t the sharpest tool in the box. Dr Hook’s lead singer is hopelessly in love with a girl called Sylvia – however the feeling isn’t mutual. In fact by the time Dennis picks up the phone to tell her not to leave him, she’s already getting ready to leave town and marry a guy from Galveston!

The writing should have been on the wall as soon as Sylvia’s mother picks up the phone.

Sylvia’s mother says she’s too busy to come to the phone

Sylvia’s mother says she’s trying to start a new life of her own

That’s kind of a bad sign Dennis. When you’re lover wants to start a new life of her own, never mind get up off the sofa to chat to you at the end of a receiver that’s pretty much rule no.1 in the international guide of -Why Does My Lover Hate Me?

Determined to press on, Dennis continues to use Sylvia’s mom as a telephonist as he tries to win back her daughter.

He says he’s only wants to keep her a while, if only to say goodbye, however Sylvia’s mom (who is just referred to as Mrs. Avery all the time) gets a bit narky and says “Don’t say nothin’ to make her start cryin’ and stay – she’s marrying a guy down Galveston way.”

Now I’m no expert but if I was the guy down Galveston way I’d be worried. First of all she’s only a few well chosen words and a hanky away from staying with Dennis, so it’s obvious the word “rebound” is in play here bigtime. She may be a fine piece of ass to have two grown men (one miles away but besotted and another idiot crying on the phone) but no good can come of this situation.

The real villain of the piece however seems to be that pesky operator who keeps asking for “40 cent more for the next three minutes”. If you were a real man Dennis you’d have told the operator to **** off, been over at the house, whisked Sylvia off her feet and booked into the local Travelodge leaving the operator to mind her own business and Sylvia’s mother to marry the guy down Galveston way instead.

Dr. Hook split in ’85 and Locorriere has forged himself a modest career as a solo performer ever since.

Mainly on the back of his constant whinging down a phone line.

Useless Trivia No 133 – British Folk rockers – They Men They Couldn’t Hang – actually wrote a sequel to the song called “Mrs Avery” which begins where “Sylvia’s Mother” ends and tells what happens next.

She’s goes after Dennis with a shotgun.


Tom Trauberts Blues

Who to Blame; Tom Waits

Chart Position; Criminally never charted.

Heartbreak Rating; 9/10. With just enough Jack Daniels to the song it could break your heart.

Tom Waits has the unique ability to sound like someone who’s eaten a bucket of gravel, washed down by four bottles of Jack Daniels and smoked 400 Superkings on the side to produce his distinctive vocals.

Try 14 days of yellow-pack Vodka and swallow a bucket of coal and you might come close to replicating the sound. Of course you’ll be doing that from a coffin but we’ve all got to go sometime. It this distinctive sound and a song boarding on all hope for humanity lost that puts Tom Waits, Tom Trauberts Blues in this chart.

It kills me having it here as I adore the tune. We all like to wallow in our own filthy self-pity every now and then and this 7 minute opus allows us that pleasure.

Just make sure there’s strong bourbon in hand (and maybe some porn directly after to perk yourself up).

Waits himself was a heavy drinker, but often used it as inspiration for his music like this classic. Either that or he was a serious pisshead.

The story behind the “Four sheets to the wind in Copenhagen” sub-title came went Waits went on the lash with a Danish model for 72 hours whilst spending some time in Denmark, however the real story is attributed to when he went down and hung around on skid row in L.A. because he wanted to get stimulated for writing this material!

Take that Phil Collins!

No writing in a cosy studio about some bird that left you and selling a million copies on the back of it - our Tom took no prisoners. Astonishingly Waits kicked it with the down and outs of L.A. with only his wits and a bottle of rye for company. He socialized, talking about second hand clothing and the quality of rat in the sewers these days before coming home, throwing up and writing this classic. The lyrics came easy – practically every one of the misfortunate’s he’d met had been put there by a woman, proving yet again that there’s nothing in this entire world that will have you rocketing to the poor house, jail, suicide or skid row, more than a woman!.

Waits combined his haunting lyrics with Waltzing Matilda – a song which resonates everywhere around the globe and of course the unofficial anthem of Australia.

Right from the opening lyric “Wasted & wounded, it ain’t what the moon did. I got what I’ve paid for now” you know this has bad news written all over it and the subsequent half a dozen verses won’t be brightening the situation anytime soon.

But what great lyrical content.

Old Bushmills I staggered, you buried the dagger

And I'm down on my knees tonight.

By the time Tom’s with “a battered old suitcase , in a hotel some place and a wound that will never heal” you’ve already played Russian Roulette and still not come across the chamber with the bullet but you know the sweet release of death might just come before Tom says;

Goodnight to the street sweepers, night watchmen,

flame-keepers an goodnight Mathilda too.

By which point you’re a broken man in a quivering wreck...or a heartless bastard!

This is a song to listen to in the bar with a bottle of scotch, packet of cigs and a gun. Then let nature take its course. On the other hand if you’ve been plagued by your woman who’s run off with the milkman (not our one, you wouldn’t put him out for the rob) and left you with memories (and 47 bills) then the right amount of whiskey might just break your heart.

Useless Trivia No; 462

Waltzing Matilda is an old Australian bush song about a swagman camping around a billabong, who captures a sheep and eats it. It turns out the sheep belonged to someone, who brings the police to arrest the swagman. The swagman fearful of being caught drowns himself in the billabong to avoid being captured.

Not give himself up, take his punishment of try pay back any himself. Christ you gotta wonder what the punishment was for munching on a bit of mutton back in the day!


Song; Without You

Who to Blame; Badfinger

Chart Position; The group never released it as a single.

Harry Nilsson brought it to Number 1 in the US.

Over the course of the day I’ve been writing about the 6 most depressing love songs of all time, so if you haven’t killed yourself by now or maybe want that suicidal three minute tune to set you running for the nearest noose then you might want to read the following.

‘Without You’, a song made famous by Harry Nilsson, strangled by Maria Carey and murdered for good measure by Celine Dion is without doubt the saddest song devoted to love in the history of music.

Over the top? .... Read on.

The song was originally recorded by English group Badfinger, made up of Pete Ham, Ron Griffiths, Mike Gibbins and Tom Evans. The song was first released off their 1970 album ‘No Dice’ (the tune has since go onto be recorded by almost 200 artists). The group’s main songwriters Evans & Ham created the hit, both from previous relationships that had broken down. Ham’s verse was ‘warm, sweet and sentimental, whilst Evans chorus ‘intense, dramatic and heartbreaking’, (Paul McCartney would later remark it was ‘the killer song of all time’). However the group never released ‘Without You’ in Europe or America, using it as a filler on Side A of ‘No Dice’ (it belatedly was released to a tepid response in Japan)

American songwriter Harry Nilsson came across ‘Without You’ at a party, mistaking it for a Beatles tune – allegedly being quoted ‘They sure know how to pick a tune’

before recording it himself. The song was an immediate hit, topping the charts in America for four weeks and spending a further five ironically in the UK. Though the song won Ham & Evans an Ivor Novello award for ‘Song of the year’, that’s about as good as it got for the group and things soon took a turn for the worse.

The group at the time were managed by an American business man called Stan Polley, who immediately signed the band to various contracts and dictated all earnings from tours, royalties and personal appearances would go into ‘Badfinger Enterprises’ however the group over time would be ripped-off by Polley’s dubious financial activities.

The group continued to have moderate success in the UK & US, were they were constantly reminded of Nilsson no.1 million-selling version.

Ripped off by Polley, and later by Warner Bros., were the group lost almost everything in legal disputes, guitarist and songwriter Pete Ham hung himself in his garage in April 1975, leaving behind a suicide note blaming their former manager Polley for everything. That night he had drank ten whiskey’s with his best friend and fellow band member Tom Evans before going home to take his life.

He was just 27 years old.

The repercussions of the act would never leave Evans.

The group disbanded for a number of years before a reunion in 1983. Times had changed and the bands following had dwindled.

On the night of November 18th 1983, after a heated argument with fellow band-members over a phone call, Tom Evans hung himself in the garden of his home. The royalties of the biggest hit the never had ‘Without You’ would pass to fellow Badfinger members, Gibbins and Griffiths, much to the anger of both Pete Ham’s and Tom Evans’ families.

Recorded over 42 years ago...the song is generally considered as a ‘classic’ (Paul McCartney regularly calls it ‘The killer tune of all time’) and given it’s awful true origins tops my list as

The most depressing love song of all time.

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