Pearl Jam – “Light Years”

Leavening the loss of one departed with a near-comical list of his workaday accomplishments (“I've used hammers made out of wood”), Pearl Jam singer Eddie Vedder realizes it's better to have loved and lost than never to have loved at all: “We were but stones/Your light made us stars.” One of the best songs on the band's sorely underrated sixth album, Binaural.

Sorority Noise – “Mediocre At Best”

“Nobody likes me/That's what I tell myself/I live alone in my own hell.” On “Mediocre At Best,” Sorority Noise concisely narrate the unmistakeable impact of rock bottom—that uncomfortable juncture where you realize that your blown relationships were likely undone by your own hand. The issue is hard to swallow; helpfully, the song is catchy enough to go down smooth.

Jimmy Eat World – “Spangle”

A cover of British band the Wedding Present, Jimmy Eat World captain Jim Adkins makes this song's beautifully insecure lyrics so patently his own with a low-key, bedroom-pop delivery on couplets like, “I'm glad you found the time to ring/I just spent all day waiting.” The pangs of post-breakup jealousy just come rushing back: “Did you say you met some neighbor?

Joy Division – “Love Will Tear Us Apart”

Before Ian Curtis' death in 1980, the revered frontman apparently experienced those telltale signs of a doomed relationship: “When routine bites hard/and ambitions are low/and resentment rides high/but emotions won't grow.” The poppiest song by Joy Division is also one of the saddest, and its music video was shot mere weeks before Curtis took his own life.

Radiohead – “Creep”

Radiohead's first big hit became a cathartic anthem for loners everywhere upon its creeping chart success in the mid-'90s. All but disowned by its creators following a reincarnation as avant-garde crackerjacks, the band has since come back around to playing the tune occasionally. The guitar blasts of “dead notes” (chugga! chugga!) before the chorus remain an alt-rock high point.

Green Day – “Boulevard Of Broken Dreams”

“My shadow's the only one that walks beside me” has got to be the loneliest line Billie Joe Armstrong has ever penned, the desolate description a fitting refrain for the Jesus of Suburbia character in Green Day's American Idiot. At this point in the proceedings, the provincial prince is coming to terms with his lonesome lot in life—it's depressing, it makes him feel half dead, yet it's home to him.

Daft Punk – “Within”

You'll never feel lonelier than when hearing a robot sing about how lonely loneliness is. “There's a world within me that I cannot explain,” lulls the somber android. On Daft Punk's “Within,” this lovelorn bot has, for some time, been looking for someone, and it's given the glum cyborg a bit of an identity crisis. Still not sad? Watch Daft Punk's Electroma and try not to cry.