Something in the Way, Nirvana
The title of this song (which doubles as the chorus) allegedly describes Cobain’s struggles with depression, i.e. there’s always something in the way of his being happy, feeling better. That sentiment paired with extraordinarily somber vocals makes “Something in the Way” one of Nirvana’s more emotional — and depressing — songs.
Is That All There Is?, Peggy Lee
“Is That All There Is?” articulates three ‘coming of age’ experiences with sheer disappointment and detachment, uniting each event with an awful disillusionment that sort of makes you not want to live anymore. The song’s mid-tempo beat attempts to mask the bleakness of its lyrics, but that dichotomy only serves to depress the listener further. In my experience.
No Surprises, Radiohead
“No Surprises” depicts sadness and disenchantment in a simple, no-frills kind of way. Radiohead has no shortage of depressing songs in their catalog, but “No Surprises” is the one to turn on when you’re feeling overwhelmingly ‘over it.’ And by ‘it,’ I mean life.
It’s Alright, Ma (I’m Only Bleeding), Bob Dylan
A protest song for defeatists, “It’s Alright, Ma (I’m Only Bleeding”) expresses Dylan’s scorn for contemporary (1965) American culture. With lyrics void of optimism, it’s difficult to listen to this song and not feel completely powerless.
Nothing Compares 2 U, Sinead O’Connor
This song so perfectly describes the initial stages of heartbreak: the desperation, the denial, and the sort of pathetic groveling only a heartbroken person is capable of. Makes me want to take Sinead out for ice cream every time I hear it.
Please, Please, Please, Let Me Get What I Want, The Smiths
There’s something about quietly begging an unknown entity for something to go right for once that strikes me as equal parts relatable and miserable.
Sometime Around Midnight, Airborne Toxic Event
The ultimate Seeing-The-Ex-Who-Broke-Your-Heart anthem, “Sometime Around Midnight” is an emotional rollercoaster that ultimately leaves you wishing your cart would derail.
Mad World, Gary Jules
This Tears for Fears cover accurately describes loneliness in a crowd without relying on cliché. While it’s not his song, Jules does “Mad World” the justice its haunting lyrics deserve.
Oh Well, Okay, Elliott Smith
“Oh Well, Okay” perfectly captures the mutual isolation that comes along with loving someone who’s suddenly become indifferent toward you. The resolution of the song is both exasperated and pained, likely similar to the relationship it describes.
White Houses, Vanessa Carlton
While it’s the most upbeat song on this list, “White Houses” is its own special brand of sad. Carlton’s story of a particularly eventful summer paints images of youth and regret in the listener’s mind. I feel 5% emptier every time I hear it.
Everybody Hurts, REM
Expected as it is, “Everybody Hurts” makes for a great depressing song because it appeals to very base, overarching emotions that you feel almost idiotic for harboring. The repetitive call to “hold on” is especially chilling when you’re in a dark place.
Brick, Ben Folds Five
“Brick” is just so goddamn sad. Before I knew anything about abortion, I knew that. Based on Folds’ high school girlfriend, the lyrics convey a secretive, confusing, heartbreaking experience that all too many people can relate to. The contrast between Folds’ trademark ‘fun piano guy’ persona and “Brick” adds another grim shade of context to the song.
As I Sat Sadly By Her Side, Nick Cave & the Bad Seeds
No list of depressing songs would be complete without a contribution from Nick Cave, whose lack of faith in humanity is evident in “As I Sat Sadly By Her Side.” If you’ve ever dated a depressed person (or been a depressed person), the air of helplessness and alienation in this song really strikes a chord.