20 Best Sob Songs from the ’90s

American singer and guitarist Kurt Cobain (1967 - 1994), performs with his group Nirvana at a taping of the television program 'MTV Unplugged,' New York, New York, Novemeber 18, 1993. (Photo by Frank Micelotta/Getty Images)
“Jumper” – Third Eye Blind (1997)
1/40

Inspired by the suicide of their band manager's gay high school friend, Third Eye Blind’s lead singer Stephan Jenkins wrote “Jumper.” Jenkins says the narrative is a plea to the bullied and the bullies – a call for compassion. Over the years, the song has resonated deeply with the LGBTQ community and those feeling similarly dejected.


“Jumper” – Third Eye Blind (1997)
2/40

When explaining the song’s lyrics, Jenkins recalls having given money to a friend for medical expenses after she’d been raped. Unfortunately, as Jenkins explains, the friend never wanted to see him again once she’d divulged her deeply vulnerable situation. Jenkins understood and used the experience to pen the song’s chilling chorus. 


“Creep” – Radiohead (1993)
3/40

Like “Jumper,” Radiohead’s “Creep” is supposedly based on true events – an unsurprising notion given lead singer Thom Yorke’s innate creepiness. In the late ‘80s, while studying at Exeter University, Yorke penned the song about a girl he’d become infatuated with. According to the band’s guitarist Jonny Greenwood, Yorke even resorted to lightly stalking the young woman.


“Creep” – Radiohead (1993)
4/40

In true industry fashion, the band eventually grew to hate the song, sometimes refusing to play it at all. Despite their disdain for the hit, it remains Radiohead’s most popular single, a fact likely to boil Yorke’s blood. When explaining why he and the band resented “Creep” so much, the singer said: It’s like it’s not our song anymore... It feels like we’re doing a cover.”


“Everlong” – Foo Fighters (1997)
5/40

Dave Grohl wrote “Everlong” in 45 minutes during a divorce that left the singer-drummer temporarily homeless. The song, however, isn’t based on his relationship with his now ex-wife. Rather, it’s about his then-romance with Veruca Salt vocalist Louise Post. When asked about the song’s origins, Grohl told Kerrang!: “That song's about a girl that I'd fallen in love with, and it was basically about being connected to someone so much, that not only do you love them physically and spiritually, but when you sing along with them, you harmonize perfectly.”


“Everlong” – Foo Fighters (1997)
6/40

Admittedly, the song’s riff is a Sonic Youth rip-off that Grohl “stumbled on” while strumming around on his guitar. Pleased with the sound, he developed the riff into one of the band’s most identifiable songs.


“Good Riddance (Time of Your Life)" – Green Day (1997)
7/40

In 1993, after his girlfriend Amanda relocated to Ecuador, Billie Joe Armstrong wrote “Good Riddance (Time of Your Life).” The homage to his relationship is filled with both anger and resolve as he strums the somber chords and shakily sings the song’s subtitle.


“Good Riddance (Time of Your Life)" – Green Day (1997)
8/40

Though “Good Riddance” is melodically contemplative and serious –  a complete divergence from the band’s previous material – Green Day bassist Mike Dirnt dubbed the single their “most punk” production.


“Tears in Heaven” – Eric Clapton (1992)
9/40
In 1991, singer Eric Clapton’s four-year-old son Conor Clapton fell from an open high-rise window in New York. The tragedy inspired the ever-poignant, Grammy-winning hit “Tears in Heaven,” wherein Clapton questions whether his son will remember him in the afterlife.
“Tears in Heaven” – Eric Clapton (1992)
10/40

Admittedly, when Conor passed, the newly sober Clapton was thrown into a “wobble.” Though he didn’t relapse and instead poured himself into his work, Clapton recalls his grief heavily affecting his decision-making: “You know when you can look back and say, 'Oh, that's why I did that’? The same could be said about the death of my son in 1991 and me getting into the weirdest relationships for the rest of the '90s…I never saw a connection until recently.”


"It's So Hard to Say Goodbye to Yesterday" – Boyz II Men (1991)
11/40

Originally written in 1975 by Freddie Perren and Christine Yarian, “It’s So Hard to Say Goodbye to Yesterday” was featured that same year in the film Cooley High. 16 years later, Boyz II Men covered the somber song for their first album, appropriately titled CooleyHighHarmony. It peaked at #2 on the Billboard Hot 100.


"It's So Hard to Say Goodbye to Yesterday" – Boyz II Men (1991)
12/40

The Motown Records R&B group dedicated the song’s video to fellow Motown artist LaTasha Rogers, professionally known as MC Trouble. The 21-year-old artist was the first female rapper signed to Motown. Unfortunately, she suffered from epilepsy and died in her sleep following a seizure on June 4, 1991.


“Under the Bridge” – Red Hot Chili Peppers (1991)
13/40

Originally penned as a poem by lead singer Anthony Kiedis, “Under the Bridge” almost didn’t make it onto the group’s fifth studio album, Blood Sugar Sex Magik. Kiedis considered the despondent song about drug use and dejection too divergent from the album’s other tracks. However, after some convincing by producer Rick Rubin, Kiedis tabled his reluctance and presented the emotional poem to the band.


“Under the Bridge” – Red Hot Chili Peppers (1991)
14/40

Unexpectedly, the song blew up and catapulted the Red Hot Chili Peppers to mainstream superstardom. Even now, three decades after its release, “Under the Bridge” – a brooding ballad about loneliness – remains the go-to joint for an introspective cruise through the City of Angels.


“Nutshell” – Alice in Chains (1994)
15/40

On April 5, 2002 – the eight-year anniversary of Kurt Cobain’s death – the body of Alice in Chains frontman Layne Staley was discovered in his home in Seattle. The lead vocalist died two weeks prior from a speedball overdose, and his badly decomposed body weighed in at only 86 pounds.


“Nutshell” – Alice in Chains (1994)
16/40

When pressed about which song reminded him most of Staley, bassist Mike Inez answered “Nutshell.” He expressed his appreciation for Staley’s “honest” songwriting, explaining that, with the song, Layne “really put everything in a nutshell for everybody.” Though the lyrics deal with depression, rejection, and death, the remaining band members often dedicate the song to Layne Staley’s memory, allowing the pain and sadness to keep their friend alive.


“Losing My Religion” – R.E.M. (1991)
17/40

In 1990, while attempting to learn the mandolin, R.E.M. guitarist Pete Buck accidentally strummed what would become “Losing My Religion.” An improbable hit, the song and its accompanying video garnered massive praise and airplay.


“Losing My Religion” – R.E.M. (1991)
18/40

Admittedly, the band’s bassist Mike Mills derived the song’s bassline from a Fleetwood Mac song, citing his inability to conjure an original chord for such a unique track. Lead singer Mike Stipe laid down his vocals in a single take, and the whole of the song’s orchestration proved relatively smooth. After the single’s release, Stipe explained its deeper meaning: “‘Losing My Religion’ is about someone who pines for someone else. It's unrequited love.”


“Don’t Speak” – No Doubt (1995)
19/40

Originally written by Gwen Stefani and her brother, former No Doubt member Eric Stefani, “Don’t Speak” was intended to be a jazzy, upbeat love song. However, when No Doubt’s bassist Tony Kanal ended the seven-year relationship between him and Gwen Stefani, the band’s frontwoman reworked the lyrics to mirror the circumstances. In 1996, it became the most frequently played song on American radio. 


“Don’t Speak” – No Doubt (1995)
20/40

Naturally, tensions in the band were high, and they considered breaking up only days before the music video was to be filmed. Instead, to remedy the strain, the band followed through with filming, even depicting the uncomfortable reality of the band falling apart.  


“Life Goes on” – Tupac (1996)
21/40

Featured on All Eyez On Me, the final album released in Tupac’s lifetime, “Life Goes On” chronicles the painful reality of losing multiple friends to street violence and incarceration. Ironically, Tupac would be gunned down in the streets of Las Vegas only a few months after the song’s release.


“Life Goes on” – Tupac (1996)
22/40

Though AllMusic described Tupac’s post-prison album as “hardened and hungry,” “Life Goes On” was a partial return to the rapper’s sympathetic, self-aware style. This time, however, Pac didn’t wallow in sadness or anger. Instead, as the song’s title suggests, the rapper implored us to accept and roll with life’s unstoppable momentum.


“Black Balloon” – Goo Goo Dolls (1995)
23/40

While the meaning behind many songs is open to interpretation, Goo Goo Dolls’ “Black Balloon” needs little elucidation. In fact, lead singer John Rzeznik plainly stated that “Black Balloon” was based on a woman addicted to heroin and her lover's desperate to save her. He’s also gone on record saying the song is more generally about “seeing someone you love that is so great just screw up so bad." Regardless, the song's overt drug references and haunting video leave little room for exegesis.


“Black Balloon” – Goo Goo Dolls (1995)
24/40

Unlike a large number of songs on the list, “Black Balloon” matches the band’s catalog perfectly. The upbeat strumming and themes of unrelenting love despite seemingly impossible circumstances scream Goo Goo Dolls.


“Adam’s Song” – Blink-182 (1999)
25/40

Adam’s Song,” which was inspired both by bassist Mark Hoppus’ loneliness and a teen suicide note he’d read in a magazine, almost didn’t make it onto Blink-182's third studio album, Enema of the State. Afraid the song was “too depressing,” Hoppus considered not presenting it to his fellow bandmates. Fortunately, he took a chance and the group was receptive. The song peaked at #2 on the Billboard Hot 100.


“Adam’s Song” – Bling 182 (1999)
26/40

Hoppus penned the song while on a nine-month tour. Single and frustrated at the fact he had no one to return home to – unlike his bandmates, who were both in relationships – Hoppus expressed his loneliness through “Adam’s Song.” Hoppus later described feeling silly and ungrateful for writing the song just as the band was on the brink of stardom. The bassist recalled, “It felt like I had too much good fortune to complain about anything.”


“Glycerine” – Bush (1994)
27/40

In 1994, Bush’s lead singer Gavin Rossdale wrote “Glycerine” about his then-girlfriend, Jasmine Lewis. Rossdale claims the writing process was less conscious and more automatic, describing himself as a “conduit” rather than a songwriter.


“Glycerine” – Bush (1994)
28/40

Rossdale also described the song as being “bigger than anything [Bush] was doing” and as having “an ancient, mystical element.” Though the music video for “Glycerine” was shot in record time due to the band’s expired visas, it won the Viewer’s Choice and Best Alternative Video awards at the 1996 VMAs.


“Angel” – Sarah McLachlan (1997)
29/40

Written in under three hours, McLachlan’s “Angel” was inspired by a Rolling Stone article focusing on heroin use and overdose in the industry. McLachlan told VH1 Storytellers the song was specifically about Jonathan Melvoin, the Smashing Pumpkin’s keyboardist. At age 34, Melvoin overdosed on heroin; his band wasn’t invited to the funeral.


“Angel” – Sarah McLachlan (1997)
30/40

Though McLachlan claims to have never used heroin herself, the singer told CMJ New Music Monthly that she’d “done plenty of other things to escape.” She went on to say that “Angel” is about "trying not to take responsibility for other people's problems and trying to love yourself at the same time.”


"I'll Be Missin' You" – Puff Daddy ft. Faith Evans & 112 (1997)
31/40

I’ll Be Missin’ You” was written in memory of Christopher Wallace – better known as The Notorious B.I.G. – after the Bad Boy Records rapper was slain in the streets of L.A. in 1997. The song is performed by Puff Daddy, Wallace’s best friend and the Bad Boy Record founder; Faith Evans, Wallace’s widow; and the R&B group 112. It samples The Police’s 1983 “Every Breath You Take.”


"I'll Be Missin' You" – Puff Daddy ft. Faith Evans & 112 (1997)
32/40

Because Puff Daddy didn't clear the sample, songwriter Sting launched a lawsuit. Naturally, Sting won the lawsuit and now owns 100% of the song royalties. According to a 2014 UCR article, Sting earns over $2,000 a day from the commemorative track. However, despite the controversy, Sting eventually performed the song alongside Puff Daddy and Faith Evans at the 1997 VMAs.


“Hurt” – Nine Inch Nails (1995)
33/40

Written by Trent Reznor and released on Nine Inch Nails’ album Downward Spiral, “Hurt” might be the band’s most anguished song. Reznor’s voice numbly crawls over pained plucking as the narrator questions his existence and worth, each lyric more chilling than the next. Some speculate that the song is a suicide note of sorts, while others describe it as a wits-end confessional.


“Hurt” – Nine Inch Nails (1995)
34/40

Though "Hurt" was nominated for a 1996 Grammy Award, Johnny Cash’s 2002 cover garnered greater acclaim. Reznor even told Alternative Press the song no longer belonged to him, as Cash’s interpretation possessed overwhelming “sincerity and meaning.”


“Save Tonight” – Eagle-Eye Cherry (1997)
35/40

The first song on musician Eagle-Eye Cherry’s debut album, Desireless, “Save Tonight” plucks and strums a grand goodbye reminiscent of Lynard Skynard’s “Free Bird.” It's the acknowledgment of an impending and painful departure, one that finds the narrator with one foot already out the door.


“Save Tonight” – Eagle-Eye Cherry (1997)
36/40

The song’s storytelling and calm yet fervent momentum facilitate sadness for what was and hopefulness for the future. The chorus implores the narrator’s love interest to live in their last moments together while he repeatedly reminds her of their inevitable separation, never explaining where he’s going or why she can’t come with him. The mystery  is enough to put a lump in your throat.


“Tha Crossroads” – Bone Thugs-N-Harmony (1996)
37/40

Written in 1996 in memory of the group’s mentor Eazy-E, “Tha Crossroads” became one of the highest-debuting rap songs of the time and the most successful song of 1996. Though it was originally written for the group’s deceased friend Wallace Laird III and debuted in 1995, Eazy-E’s untimely death inspired the rewrite that garnered massive praise.


“Tha Crossroads” – Bone Thugs-N-Harmony (1996)
38/40

The music video matches the gravity of the song. Initially, we see someone we assume to be a grim reaper figure collecting the souls of loved ones. Eventually, the reaper ascends toward heaven, revealing himself to be an angel.


“Something in the Way” – Nirvana (1991)
39/40

Perhaps the most poignant song on the list, Nirvana’s “Something in the Way” sums up the mind-bending riddle that is depression and desolation. According to Kurt Cobain, the song’s composition was fantastical by nature: “if I was living under the bridge and I was dying of AIDS, if I was sick and I couldn't move and I was a total street person. That was kind of the fantasy of it.”


“Something in the Way” – Nirvana (1991)
40/40

Though not entirely autobiographical, there was a short time when Cobain was homeless, sleeping in cardboard boxes and “hallways of old apartment buildings.” The late-great vocalist channeled despondency and suffering like none other, his palpable pain capable of inducing cold shivers every time his voice cracked into the microphone.


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