These 5 Sad Songs From the 1990s Are Guaranteed To Make You Cry

Soul Asylum once suggested that sad people might start a company called Frustrated Incorporated. Misery loves company, they say. The band critiqued how sadness was getting packaged and sold in the 1990s. However, corporate cynicism aside, sad songs remain timeless because sometimes you just need to wallow a little in your own gloom. And if you’re in the mood to go moist in the eyes, these tracks from the 1990s are guaranteed to make you cry.  

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“Hurt” by Nine Inch Nails

When Nine Inch Nails released “Hurt” in 1995, Trent Reznor was a month away from turning 30. It appeared on The Downward Spiral, which also explains the song’s dark sentiment. In 2002, Johnny Cash covered “Hurt” and shifted Reznor’s despair from emotional frailty to the fleeting and frail reality of life generally. Still, Reznor’s original encapsulates profound sadness, and the moment when one succumbs to despair. Keep the Kleenex nearby.

“Nothing Compares 2 U” by Sinéad O’Connor

Few singers are capable of recording the definitive version of a Prince song. But Sinéad O’Connor did so with “Nothing Compares 2 U” from I Do Not Want What I Haven’t Got. O’Connor used her voice as an outlet for pain, trauma, and rage—a defiant and bold singer who sang blistering punk and gorgeous hymns, sometimes within the same song. She also filmed one of the most striking music videos of the 1990s, a single close-up shot, crying as she overcomes loss and abandonment.   

“Needle In The Hay” by Elliott Smith

If you’re of a certain age, you won’t forget the image of Richie Tenenbaum’s bathroom scene in The Royal Tenenbaums to the sound of “Needle In The Hay”. That was 2001, and Smith would die violently two years later. But “Needle In The Hay” also opens Smith’s self-titled 1995 album. It’s one of his most powerful songs, which, if you’re familiar with Smith’s music, is saying something. He uses a heroin metaphor, but the mounting anxieties here cover more than addiction.

“Street Spirit (Fade Out)” by Radiohead

Thom Yorke’s saddest song concludes Radiohead’s second album, The Bends. The narrator can feel death around him, “can see its beady eyes.” Yorke sings over Ed O’Brien’s dark arpeggios, with his chords scoring a kind of dirge. By the end, Yorke has layered his voice, which mimics the spirits tugging at a living person from the other side. Just like in The Famished Road, Ben Okri’s novel that partly inspired the song.

“Everybody Hurts” by R.E.M.

Don’t they, though? This is one of Michael Stipe’s most tender performances. Peter Buck plays a delicate lullaby on his guitar as Stipe turns one of the simplest ideas into a masterpiece ballad. “Hold on, when you feel like letting go.” It’s hard not to think of Kurt Cobain, Stipe’s close friend, when I hear this song. “Everybody Hurts” ends with Stipe repeating, pleading, imploring: “Hold on.” With one of America’s greatest rock bands lifting him in a lilting waltz, accompanied by a gospel organ and swelling strings.

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