“Every one of Joel’s songs — including the happy ones — are ultimately about loneliness.” – Chuck Klosterman

For a singer known best as a Tin Pan Alley-inspired, Broadway-loving, pop balladeer, Billy Joel has a pretty big dark streak. You may not hear it in “Just the Way You Are” or “Uptown Girl,” but Joel’s catalog is flecked with songs that reveal his unhappy side — the part of him that attempted suicide in 1970.

So many of Joel’s songs are about relationships ending, or relationships doomed to fail, that you could find a hundred that touch on his lingering sadness and loneliness. Listed below, though, are the ones that are downright bleak — the ones that depict a desperation or meaningless that surpasses his usual melancholy.

Counting down to his darkest moments, here are Billy Joel’s ten bleakest compositions.

10. Pressure (from The Nylon Curtain, 1982)

You will come to a place / Where the only thing you feel / Are loaded guns in your face

In a writer’s block, his marriage falling apart, and attempting to create a “sonic masterpiece” as a tribute to a recently assassinated musical inspiration (John Lennon), Billy Joel was coming apart at the seams in the early eighties. The Nylon Curtain was his darkest album since 1973’s Piano Man, and its most intense and bitter song was “Pressure.”

Joel addresses someone younger and unfazed who has a more positive look on life, claiming that insatiable demands from all around eventually catch up with everyone, whether or not they’re ready (“Here you are with your faith / And your Peter Pan advice / You have no scars on your face / And you cannot handle pressure”).

9. Souvenir (from Streetlife Serenade, 1974)

Every year’s a souvenir / That slowly fades away

It’s Joel’s shortest song, both in play time (1:59) and in word count. In just ten lines, Joel characterizes memories and experiences as “souvenirs” that “turn to dust” — his nonstop struggle to find enduring meaning is a common theme of his darkest work.

A plaintive (but beautiful) arrangement of Joel’s singing accompanied by only piano match the sparse lyrics capturing the void in Joel’s life. For many years, he closed every show with this number.

8. Running on Ice (from The Bridge, 1986)

I’m carrying the weight of all the useless junk / A modern man accumulates / I’m a statistic in a system

The lone truly and completely happy album in Joel’s discography, An Innocent Man, came out in 1983 after Billy Joel fell in love for the first times after divorcing his first wife. Three years later, though he was happily married to Christie Brinkley, his sense of aching and longing — that he doesn’t belong and can’t keep up with the world — had returned.

Whatever the reason, there’s “a new disaster every time I turn around” and “as soon as I get one fire put out / there’s another building burning down.” No matter what he tries or what he does, he’s “running on ice,” failing to gain any traction in moving forward and settling down just when things were supposed to be going his way. From his perspective, the world is constantly moving faster and colder, and he’s increasingly disconnected. His whole life is “a bad waste, a sad case, a rat race / it’s breaking me.”

7. Close to the Borderline (from Glass Houses, 1980)

It isn’t new what I’m going through / But everybody knows you have to break some time

Joel felt like he had been pigeonholed through his late-70s breakout as a crooner and balladeer. Anyone who had been paying close attention would’ve known his uptempo numbers were just as consistently strong as his ballads. Still, he put together Glass Houses, an (excellent) attempt at an all-rock album.

The second last track on the album, “Close to the Borderline” was written as a response to the snark of new wave artists like Elvis Costello. But Joel’s take on dark, brutally honest humor reveals that his interior persona is just as bitter and broken as his darkest songs make you think. He casually jokes about bums dropping dead, drug addiction, and teenage suicide. It’s not a pretty picture.

His inability to adapt to a fast-paced, modern life (a recurring theme of his music) is evident here. He laments his dependence on his doctor, lawyer, and banker, rejects the sensationalist bad news-focused media, and describes how none of it provides any value. Worst of all, he has to endure pressure and heavy responsibility: “Life is tough, but it’s just enough / to hold back the tears until closing time.”

6. Falling of the Rain (from Cold Spring Harbor, 1971)

It seems time has brought things to an end / And nothing’s changed / ‘Cause you can’t stop the falling of the rain

In “Falling of the Rain” off of his first solo album, Joel tells a story of a painter who “is a fool” and whose “mind is filled with hopeless dreams.” There’s also a “girl in braids,” and the two seem destined to fall in love. But they never do. He remains obsessed with painting, and she moves on with her life.

Assuming the painter is a stand-in for Joel, this song shows him struggling with his obsession with his art, using it as an explanation for his isolation from the world. He can’t face “the falling of the rain” — or, the trials and challenges of the real world.

5. Somewhere Along the Line (from Piano Man, 1973) 

You pay for your satisfaction / somewhere along the line

The central thesis of “Somewhere Along the Line” is that there’s a hefty and inevitable price tag to happiness, that all good things ultimately sour and destroy us. He singles out the fact that his “belly’s full of fancy wine,” and thus “in the morning there’ll be hell to pay.” He also calls out his “sweet Virginia cigarette” which is “eating up inside of me.”

But Joel’s concerns are deeper-seated than a simple, finger-wagging “indulgence is bad” message. He concludes the song by stating “a young man is a king” but “there’s an old and feeble man” not so far behind. He can’t enjoy even his fleeting moments of happiness. He just waits for it to eventually come crashing down on him, whether it’s the sharp pain of a hangover or the gradual futility of old age. “Somewhere Along the Line” suggests that not only is Joel devoid of happiness, he’s somewhat terrified of finding it in the first place.

4. Where’s the Orchestra? (from The Nylon Curtain, 1982)

I assumed that the show would have a song / So I was wrong

In 1982, Billy Joel was a multi-millionaire. He was coming off a six year span in which he released five albums, each of which was masterpiece or darn close (in my eyes, at least). He was a self-made man and an international celebrity. Through hard work, great craft, and good luck, he had achieved virtually every career goal he had ever dreamed of, all by the age of 31.

So, to use his thinly veiled metaphor, where was the orchestra? Where was satisfaction and pleasure and meaning of it all? He’d made it to the big leagues. This was his “big night on the town,” where every thing is supposed to start making sense. He’s not sure if he’s “missed the overture,” but nothing in his life made any more sense than when he drank a bottle of furniture polish twelve years earlier. Night after night, the “curtain falls on empty chairs” — the gaping hole of loneliness that is life.

The whole production of living remained a mystery to him, an almost-pointless endeavor. “Where’s the Orchestra?” captures Joel’s absence of meaning and cohesion with a simple, heartbreaking analogy.

3. A Minor Variation (from River of Dreams, 1993)

When troubles want to find me / I ain’t hard to find / They know where I am / Like a hungry pack of wolves

Age, an ever-growing fortune, and a steady marriage to a supermodel did a lot to temper Billy Joel as he passed the age where it was acceptable for him to be a pop star. In 1993, he was 43.

But some things never change, and that’s the point of “A Minor Variation.” No matter how long he weathers them, his demons never disappear (“ain’t no way to fight them / ain’t no way around them”), and they still strike hard. He sounds here like a seasoned vet, one who has accepted the that even his fleeting pleasures are slipping away.

For one, his multi-decade high of relevance and popularity was diminishing, and it hurt just as much as he predicted it would in 1973 in “Somewhere Along the Line”:  There’s “no way to win when you’ve already been forgotten” and “it’s all a part of a pattern” of rise and fall.

He’s so fully given up hope that he’ll ever escape his occasionally-crippling depression and loneliness that he’s “getting to the point where I don’t feel the pain.”

“A Minor Variation” is the song of a man who spent his whole career struggling to find personal hope and meaning, and failed. Twenty-one years after his debut, he said goodbye just as broken and defeated as ever.

2. Captain Jack (from Piano Man, 1973)

You can’t understand why your world is so dead

I think of “Captain Jack” as Billy Joel’s version of Dante’s “Inferno,” a spiraling, eight-stanza descent into his darkest demons and addictions. But, unlike Dante, Joel refuses to fully reject the sin and temptation he observes.

Joel’s cover story for the song is that he used to observe teens buying hits from a drug dealer known as Captain Jack, and he wanted to write a song about these kids as a warning against drugs. But it takes little more than a cursory listen to sense that there’s something deeper going on here, that the protagonist is a stand-in for the hurting songwriter with a history of alcoholism and an inability to adjust.

Captain Jack becomes not strictly a drug dealer but any means of easy, temporary escape from the tragic, senseless world: drugs, sex, even art. Rather than show a light at the end of the tunnel, Joel depicts a numb and broken young man who “can’t understand why [his] world is so dead,” a persona he never fully grew out of.

1. Tomorrow is Today (from Cold Spring Harbor, 1971)

I’ve seen a lot of life / And I’m damn sick of living it

“Tomorrow is Today” is adapted from a suicide note that Joel wrote in 1970 when he drank a bottle of furniture polish in an attempt to kill himself. It’s an explanation of his frame of mind, why a twenty year-old decided that “soon enough it will all be over.”

The title of the song has two meanings. The first is that “tomorrow” — the great beyond, the big sleep — would be coming “today,” plenty early. The second meaning of the title, and the one explored by the words of the suicide note/lyrics, is that each passing day had become identical for the musician. “I don’t need to know the hour / because it’s passing anyways.” With no sense of efficacy or esteem, living each moment bereft of meaning, Joel has no need or interest in seeing what the next day brings.

The best efforts of the people around him, who tell him “life is sweeter,” make no impact. He submits to his suicidal impulses. In the centerpiece verse of the song, descends to “the river,” where he says his farewell: “Made my bed / I’m gonna lie in it / If you don’t come / I’m sure gonna die in it.”

The song ends with perhaps the most haunting, conclusive words Joel ever wrote: “Though I’m living and I’m singing / And although my hands still play / Soon enough it will all be over / ‘Cause tomorrow is today”

Of course, Joel survived his suicide attempt and went on to a personally tumultuous but commercially successful career. It’s strange to think how much the world would have lost if his attempt had worked. Though he was rescued from poison, he was never fully rescued from the melancholy and demons that made him drink it. And we witness that pain linger for decades, speckling his albums with the loneliest, most disheartened, and bleakest songs you’ll ever hear dismissed as “adult alternative.”

I want to thank Joel for sharing this part of his world with us and giving us a better insight into the darkest depths of the man behind the great music.