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50. Neutral Milk Hotel – “Holland, 1945” (1998)

For such a rejuvenating song, Jeff Mangum poured his soul into the lyrics but couldn’t have cared less about the title — he just told art director Chris Bilheimer to use either “Holland” or “1945,” so we got the combination of the two. Maybe that’s the key to Neutral Milk Hotel’s loveability. They’re not trying to pick at every detail to make a “perfect” song, they just want to create. “Holland 1945” was inspired by the diary of Anne Frank, with Mangum writing a beautiful love song for this poor girl who’s life was taken much too soon. While the subject matter is certainly dark, Mangum creates a new life for her, set to a charming tune; it’s hard to even realize what he’s singing about if you lose yourself to the catchy trumpet riffs. — Virginia Croft


49. Björk – “Joga” (1997)

In the music video for “Joga,” we see tectonic plates and forms of land break apart in an odd, rhythmic manner, with an early computer game layout. The track has a strong sense of uncertainty, Björk not sure if she can trust others or her surroundings. Yet it’s sometimes hard to focus on her vocals, the string octet almost more enticing than Björk herself.  Here, she gives the impression of a push and pull with the octet, savoring the unrest and dissonance within as she repeats, “State of emergency, how beautiful to be.” The instrumentals are reminiscent of a medieval adventure, Björk pulling us into the universe only she could create. — Virginia Croft

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48. Pavement – “Summer Babe (Winter Version)” (1992)

Though their first release was an EP in ’89, Pavement are a pure-’90s band with only five albums to their name spanning ’92-’99. If you side-step their first three EPs (compiled together in ’93’s Westing (By Musket and Sextant)), the “Summer Babe” single is what you reach first, and it’s probably the most representative of the Pavement style. The arrangement is fuzzed-out and dense but not threateningly so, and Malkmus sings through with a tone and humor that’s dryer than the Sahara. The lyrics are cryptic starting off with a Vanilla Ice reference and distractingly-specific details like “protein delta strip” and a “plastic-tipped cigar.” It’s Pavement, and if you love or hate them (please don’t let me find out you hate Pavement), “Summer Babe” is the one — though, not their most popular or best (wink, wink). — Andrew Cox

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47. Cocteau Twins – “Cherry-Coloured Funk” (1990)

The Cocteau Twins released a couple singles from their most critically-acclaimed album, Heaven or Las Vegas, but the non-single “Cherry-Coloured Funk” has become their most popular song anyway, eclipsing the other tracks by 2-to-1 on Spotify streams. It’s the opening track of the album and sets the pace for the album’s themes of a balance between life and death, darkness and light. The song’s constructed around a simple, dance-based tom and kick groove, and Elizabeth Fraser’s vocals float through the mix as she sings of being tugged down through the tiger’s mask. What the tiger’s mask means is up to you, and it seems the Cocteau Twins would want it that way. — Scott Hale

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46. Massive Attack – “Unfinished Sympathy” (1991)

Massive Attack renamed themselves Massive for a brief point in ’91 to avoid being associated with the Gulf War, and it coincided with the single release of “Unfinished Sympathy,” the group’s most emblematic release. There’s a reason Massive Attack have this larger-than-life aura, especially in the UK; they arrived in nobody’s shadow. Their influences come from a myriad of places — hip-hop turntablism, underground electronica, rave culture, Diana Ross, etc. — but there’s no single prior artist you can point to and say that Massive Attack clearly wanted to be. The UK music press had to invent a new genre term to explain their music: trip hop. If you’re looking for the moment that the ’90s separated from the ’80s musically, there was no turning back after “Unfinished Sympathy.” — Andrew Cox


45. Destiny’s Child – “Say My Name” (1999)

In conversation, saying someone’s name is a psychological backdoor into increased affection. We respond well to being acknowledged. It’s why Beyonce croons the title lyric repeatedly, daring her man to validate their relationship with just her name. In the context of the song, saying her name out loud would mean informing “another lady” of her existence, but it’s also a gesture of hope. If only he can call her baby, can say her name, then she can reject her fears of betrayal. All that mixed in with the thudding beat and punching vocals? No wonder we are still saying Beyoncé’s name two decades after this song’s release. — Heather Jensen


44. Elliott Smith – “Needle in the Hay” (1995)

The appearance of a needle in a song title should be an alarm bell if you’re wondering what the song’s about. Smith’s first classic was a breakthrough in the Pacific Northwest indie scene, where heady minimalist folk could be as punk as Bikini Kill. It’s truly a perfect song with double-meanings and Portland references piling up right under your nose. As what any good song or art about heroin has to do, “Needle in the Hay” digs deeper into what dependency truly means and what holes have to be filled. The final mix thankfully took out a trumpet and harmonica, letting certain words and sounds, like the drawn-out “s” in “marks,” resonate deeper. — Andrew Cox


43. Depeche Mode – “Enjoy the Silence” (1990)

There’s a very barren feeling to Depeche Mode’s addictive track. “Enjoy the Silence” is far from quiet, with dissonant synths and Dave Gahan’s haunting vocals. In the band’s music video, a king travels to beautiful landscapes, with the sole purpose to enjoy them alone. Perhaps it really was all he ever wanted and all he ever needed, as the lyrics imply. On the other hand, the video leaves the viewer with an uneasy feeling, wondering how happy this king can really feel in a constant state of aloneness. “Enjoy the Silence” bands together the lonely, offering respite for those tired of dancing to tunes too upbeat for their liking. — Virginia Croft


42. Missy Elliott – “The Rain (Supa Dupa Fly)” (1997)

Missy “Misdemeanor” Elliott arrived fully-formed and as much an oddball pop tour de force as OutKast with “The Rain (Supa Dupa Fly).” Not enough people know this, but she brought Timbaland out of their neighborhood in the early ’90s. Missy recruited Timbaland onto his first released tracks with Jodeci in ’93. The first full album Timbaland produced was for Sista, Missy Elliott’s R&B group. Elliott and Timbaland worked as a songwriting/producing duo for Aaliyah on One in a Million. Let me clarify: the story of pop music and Timbaland production in the late-’90s/early-’00s does not happen without Missy Elliott. She would be an integral figure in the ’90s even if she never made solo work. But she did. “It be me me me and Timothy,” indeed. — Andrew Cox

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41. Spiritualized – “Ladies and Gentlemen We Are Floating in Space” (1997)

There are few rock songs from the 90’s—or any other decade—that have the emotional heft, the immediate impact that the title track from Spiritualized’s 1997 masterpiece Ladies and Gentleman, We Are Floating In Space does. The song (and record) begins with only the unaccompanied voice of Kate Radley—who two years previous had left both the band and the song’s author Jason Pierce and married The Verve’s Richard Ashcroft in secret—stoically uttering the song’s title. It’s an amazingly bold choice, one that informs the listener that what follows will be something light-years beyond your typical broken heart song. Aided by the Balanescu Quartet and Londogayn Community Gospel Choir, a decimated J Spaceman warbles “All I want is a little bit of love to take the pain away” in a manner so hobbled the listener is shot through space and time directly into Pierce’s obliterated heart and psyche. By the time the Elvis’ “Can’t Help Falling in Love” is interpolated into the song (something Presley’s estate originally sued Pierce over) most any human who has ever had their heart wrenched from their chest will be awash in goosebumps. I still am each and every time I hear this beautiful song. — Donovan Farley


40. Underworld – “Born Slippy (NUXX)” (1995)

Made famous by being featured in the panic inducing film Trainspotting (sorry, that’s all it induced in me!), “Born Slippy (NUXX)” is still worth praising as its own freestanding composition. While the vocals may sound relaxed, there’s a tense urgency to reach the listener, the vocals almost pushing faster than the instrumentals. It’s a song of distracting excitement, fit for an underground bar or dance hall. It’s hard to think of anything else while listening to Underworld’s intoxicating and enticing, pulsating beats. The track is easy to fall into, encapsulating the listener from deep within, pulling them away from their world as long as possible. — Virginia Croft


39. Wu-Tang Clan – “C.R.E.A.M.” (1993)

Wu-Tang clan are forever indebted to the vaults of Stax legends, such as David Porter and Isaac Hayes (samples which emerged from the crates of the RZA) and 1993’s “C.R.E.A.M” is no different case. It’s a quintessential example of the early 90’s East Coast/New York sound which producers like RZA helped craft in response to a booming West Coast scene pioneered by groups like N.W.A. and producers like Dr. Dre. The eighth track on Enter the Wu-Tang (36 Chambers), the group’s studio debut, “C.R.E.A.M” makes use of a simple, hypnotic loop coming from The Charmels’ 1967 recording “As Long As I Got You,” released on Volt. Peaking at 60 on the Billboard Hot 100, “C.R.E.A.M”. has been lauded by many critics as one of the greatest hip-hop songs of all time, “still devastatingly layered,” according to Jason Lipshultz of Billboard. C.R.E.A.M. is the Wu-Tang Clan’s highest charting track, gaining RIAA certified Gold status in 2009. — Scott Hale

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38. DJ Shadow – “Midnight in a Perfect World” (1996)

DJ Shadow’s lone classic Endtroducing… is often treated as the spurring of a seismic shift in electronica, underground hip-hop, and plunderphonics/sampledelia. Even in the ’90s, instrumental hip-hop wasn’t respected as an official genre, though it had been thriving in clubs and underground since the ’80s. The most public acceptance of it would be on tracks within larger hip-hop records — think of “DJ Premier in Deep Concentration” or all the way back to “The Adventures of Grandmaster Flash on the Wheel of Steel” in ’82. It would take a talent outside of the normal hip-hop scene to craft a whole album around instrumentals — the samples and drum programming were enough to not only make compelling music but be the best of its time. The most significant track off it is “Midnight in a Perfect World,” which is built from an obscure breadth of samples from David Axelrod to Organized Konfusion. Without Endtroducing…,  The Avalanches and J Dilla don’t have a template to build off of. — Andrew Cox


37. The Breeders – “Cannonball” (1993)

The Breeders became a sensation in the ’90s from the necessity for an extra creative outlet. Initially only a side project, Pixies bassist Kim Deal’s project became a full time gig due to the popularity of songs like 1993’s “Cannonball” of their album Last Splash. This track is like a beautifully incoherent collage made by your 7-year-old little sibling in art class: you have no idea how it came together but you can’t stop looking at it. Traces of the Pixies’ sound can be heard, but so can Sonic Youth, Nirvana, Dinosaur Jr., Stereolab, the list goes on. “Cannonball” was the greatest commercial success for the Breeders, even remaining charted for 30 weeks straight in France. — Scott Hale


36. The Orb – “Little Fluffy Clouds” (1990)

Rickie Lee Jones was a great mostly-forgotten folk/yacht rock artist from the late ’70s, but in electronic music lore, she remembered looking up at the sky when she lived in Arizona. She’s the voice behind the iconic sample in The Orb’s ambient house classic. When people say the early ’90s was the most free-spirited era in music history, “Little Fluffy Clouds” is at the center. The boldness of the track comes from the 40-second sample, which is played in full twice. It’s not melodic, but when listened to over and over again, as many have, you start to trace the rhythm of Jones’ speech pattern. I don’t know if this had a goal, but it ends up proving something new: under the right circumstances, we can make melodies out of anything. Just like in the skies, there’s beauty everywhere; there’s music everywhere. — Andrew Cox


35. Foo Fighters – “Everlong” (1997)

“Everlong” is a love song from a punky perspective, resplendent with rock riffs and hopeful lyrics. For a song with such a masculine, alternative sound, the lyrics dig into sincerity, acknowledging the harmony of two people well-matched in love. Dave Grohl is reassuring himself, turning “Everlong” into a metaphorical lullaby with the musical tone reversed. He matches his words with fast-paced, mountainous rhythm. The song journeys to simply ask his newfound lover to “promise not to stop” singing by his side. It’s an ode to new love wrapped up in grunge-y casing, a song that asks even the listener to sing along. — Heather Jensen


34. TLC – “No Scrubs” (1999)

Get in girls, we’re going out! And what am I playing on blast the entire car ride, you ask?

No Scrubs, of course.

“Wanna get with me, with no money — oh no.” Oh no indeed sis. The bar was set higher in 1999, okay?

We are forever indebted to the ’90s for many musical feats and “No Scrubs” is arguably the most iconic song to come out in ‘99. We give many thanks to the hitmaker She’kspere and even more thanks to T-Boz, Chilli and Left Eye.

We thank these folks for a song that carries in every divinely-feminine situation. You’re riding around with your girls? “No Scrubs.” You’re pregaming with your girls? “No Scrubs.” You’re about to give birth? “No Scrubs.”

It’s simple. Whenever you need a pick-me-up or power boost. Play the reminder of self-love that is “No Scrubs.” — Chanell Noise

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33. My Bloody Valentine – “Only Shallow” (1991)

While shoegaze was running rampant in the 90s (thankfully!), there was something so different about My Bloody Valentine’s approach. Their brand of the genre was much more dynamic, with layers upon layers of instrumentals and effects that were not otherwise being used. “Only Shallow” is a harsh representation of shoegaze, pulling on its punk roots to create a hard rock version of melancholy. It’s rough around the edges with an inside worth making the time for — its discord providing a strange sense of cathartic relief. — Virginia Croft

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32. 2Pac – “Ambitionz Az a Ridah” (1996)

To write about Tupac is to write about reincarnation, twoness, immortality, or a militarized determination in the form of gangsta rap. Going straight from jail to the studio to lay down “Ambitionz Az A Ridah,” Tupac exchanged bail money for a contract with Death Row. Now I know a bad extended metaphor when I see one, but hey, life goes on. This new life signaled a departure from the politics of his past to incorporate a whole new persona:

 Uh, yeah, and now you got me right beside ya, hopin’ you listen

I catch you payin’ attention to my ambitions as a ridah

He hopes you listen, to his transition, to his alter ego, to how power may sound and how it may change. The fame he worked so hard to achieve—the visibility, finally, after historical negligence—none of that matters in the face of violence. I mean, this is the song that white boys listen to so they can feel hard. No amount of Machiavelli studied in jail can negate the tensions within Pac’s identity. This album may be the ramblings of a man overwhelmed, but he was never worried about that. It is much easier to front. He answered his own questions.

His “murderous lyrics, equipped with spirits of the thugs before” played the part to risk something bigger and greater. In the current age of Twitter fingers and fake news and general pettiness, it becomes inevitable to miss the honesty of Tupac. He has no ghostwriter; he is a ghost writing. You can’t make that shit up. Conflicted, poetic, almost: “When it’s time to die, to be a man and pick the way you leave.”

I mean fuck it, in retrospect, it just sounds right. When we ride, we die.

The song shows that people can listen to something without endorsing it, that Tupac can rap about something without believing it, that identity politics is that which it is—politics—that “history’ll prove authentic.” — Lagnajita Mukhopadhyay


31. Fiona Apple – “Criminal” (1996)

“I’ve been a bad, bad girl,” sings Fiona Apple in the opening of “Criminal,” the biggest hit off her debut album Tidal. This line sets the tone for the rest of the song, leading into a sultry tune about the guilt that comes with using sexuality to get what you want. Apple blends elements of rock and jazz and employs her husky vocals to create a pop song with a sexy, almost sinister feel to it. Even more impactful than the song itself was its controversial accompanying music video, a similarly eerie clip showing Apple in varying stages of undress, which received harsh criticism from the media based on the way the singer looked. Because of this scrutiny on her body and appearance, the songstress uttered these four words while accepting her Best New Artist award at the 1997 MTV Video Music Awards: “This world is bullshit.” At this moment, Apple established herself as someone who wouldn’t be part of the pop machine, someone who would play by her own rules. For that, we have the criticism of the “Criminal” music video, and thus the song itself to thank. — Drew Pearce

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30. Weezer – “Say It Ain’t So” (1994)

There are songs that everyone knows because somewhere along the timeline of humanity they were deemed classics. And then there are songs that became bigger hits and achieved wider fame when they were chosen to be on the 2007 hit Wii game Rock Band. “Say It Ain’t So” might be one of these bops. I am fully familiar with every instrument that makes up this sensationally emotional song because I have played it countless times. My personal favorite part is singing the line “Something is bubbling behind my back” because of the fun melody. As I write this, I rethink my favorite part. It might be the explosion into the chorus, the surprising and cryptic bridge, or the truth of the matter being that your drug really is a heartbreaker. Either way, I am headed to my dingy basement to feel like a star as I play those plastic drums to the beat. — Sadie Burrows


29. Britney Spears – “…Baby One More Time” (1998)

This song feels like it can only be appropriately played in a junker car with all the windows rolled down, probably post-break up, and preferably while speeding. Though not exactly the deepest lyrics in the world, this song begs for love without sounding like it’s begging, the urgent piano and Spears’ rhythmic vocals anything but desperate. Sure, maybe Britney wants him back, but she’s okay with finishing her hit first. Even without the nostalgia embedded around every “hit me, baby, one more time,” this is essential listening for any late night drive, any post-breakup screaming sesh, and, really, any playlist of your choosing. — Heather Jensen


28. Daft Punk – “Da Funk” (1995)

When people think of Daft Punk, it’s not necessarily this. The LED masks come to mind first — those started out after 01’s Discovery. There are sounds that are associated with Daft Punk nowadays like disco and French pop, but “Da Funk,” their first hit single, is distinctly hard techno. Considering all that, it still doesn’t mean Daft Punk didn’t have an impressive aesthetic that immediately changed electronic music. It was digital but not lifeless — sonically complex but not dense. Their drums and synths bounced like funk music, hence the title. At the end of the day, the song is just beautifully-constructed with four distinct parts coming in and out of the mix and layering over each other by the end. It’s symphonic but also just pure fun. — Andrew Cox


27. Radiohead – “Fake Plastic Trees” (1995)

Hear me out, the hit Netflix original, Ozark, would be nothing without its score! The show employs some use of Radiohead, though not enough in my opinion. Imagine Bateman’s character coming home from a nefarious mission all beat up and falling into his family’s arms as Fake Plastic Trees plays?

Epic right? I mean the show is set in the Ozarks in Missouri. If you haven’t seen the series or aren’t familiar with the area, I can confirm there are plenty of trees.

Come to think of it, I hear Radiohead on lots of television and movie series. Think How I Met Your Mother, Twilight, CSI, Quantico, Community, YOU.. the list goes on! Plenty of scenes in drama need that cool-down that only alternative rock can provide.

If I may, below I pitch some more productions that can benefit from Radiohead’s “Fake Plastic Trees”:

Future Fallout game sequences

Sims 4 radio stations

More Ozark episodes

College graduations (irl)

All American


Better Call Saul


Really any crime drama or political drama. — Chanell Noise


26. Nine Inch Nails – “Closer” (1994)

I love that Reznor is annoyed that his biggest song is misinterpreted as a lust anthem. I mean, the chorus only goes, “I wanna fuck you like an animal” — how could they have reached such a conclusion? It doesn’t help that the song is just sexy, in a kinky nightmarish way. As the song unfurls and keeps throwing out synth riffs that would make George Clinton jealous, you envision just dancing maniacally with someone you don’t know and absolutely nothing matters. Nine Inch Nails made multiple classic albums and are still making vital music, but without this song, Reznor and co. might just be a cult act. — Andrew Cox


25. Elliott Smith – “Waltz #2 (XO)” (1998)

Writing about Elliott Smith feels like something I shouldn’t be allowed to do, since my words could never begin to capture the weird mixture of joy and melancholy that his songs conjure up. But “Waltz #2 (XO)” is an incredible song, so I’ll do my best. At first listen, it sounds like a love song Elliott Smith wrote for someone he might have been interested in dating, but in true Smith fashion, there’s so much more to it than that. It’s a song of empathy for his mother, who had to hide her emotions after enduring abuse from Smith’s stepfather. The song examines one night between Smith, his mother, and stepfather, and results in a realization for Smith: he’ll never truly understand the pain his mother is feeling. It’s a selfless observation, refreshing, and honest. — Virginia Croft


24. Built to Spill – “Car” (1994)

As we get older, the resistance to responsibility is more and more intriguing. On their song “Car,” Built to Spill offers a place to call home for all of us who don’t want to be grown up, at least not today. When Martsch sings “I wanna see movies of my dreams,” his wish is an earnest one—wouldn’t it be nice to spend all day rewatching the scenes you created while taking a break from life? Moreover, wouldn’t it be nice to spend both your waking and dreaming state disregarding reality? If we can’t actually do that, at least we can listen to “Car” and pretend. — Virginia Croft


23. Mobb Deep – “Shook Ones, Pt. II” (1995)

Released off Mobb Deep’s breakthrough 1995 commercial and critical success, The Infamous, “Shook Ones, Pt. II” is considered one of the greatest hip-hop tracks of the ’90s by fans and critics alike. Part one was their 1994 Loud Records debut and is practically nonexistent compared to this sequel, which was the lead single for The Infamous and is treated as their true introduction. Complex ranked it as the 23rd-most violent rap song of all time; lines like “Rock you in your face, stab your brain with your nose bone” certainly helped build its case. — Scott Hale


22. The Verve – “Bitter Sweet Symphony” (1997)

Britpop needed a funeral anthem by the time Oasis’ ill-fated third album arrived, and The Verve’s strings-sampling epic fit the bill. With a heavy-loaded arrangement, Richard Ashcroft keeps the lyrics simple through repetition; the chorus starting with “No change, I can change” is just brilliant in its elastic flow. The story around the lawsuit with the Rolling Stones manager over the string sample is enough to make you hate the music business forever and have you always question a plagiarism accusation. The strings are the core of the song though and has helped make “Bitter Sweet Symphony” quite possibly the biggest alternative hit of the decade, and nobody can take that away. — Andrew Cox


21. Jay-Z (ft. UGK) – “Big Pimpin'” (1999)

This snuck right into 1999 with a Dec. 28th release off the otherwise mostly-forgettable Vol. 3…Life and Times of S. Carter. The single would be released in 2000, be a big hit, and be routinely discussed as one of Jay-Z’s best. Timbaland makes the classic beat here, and it’s on par with “Get Ur Freak On” as his best work; the outro makes that especially clear. UGK do their thing by bringing a Texan southern drawl to this big-time New York affair. Everybody is just at their peak, and the result is one of the greatest posse-cut, shit-talking anthems ever. — Andrew Cox


20. Nirvana – “Smells Like Teen Spirit” (1991)

If you’re going to look into the ’90s, you have to take a long hard look at grunge. The movement kind of stank but yielded some great fashion moments (who doesn’t appreciate a good oversized flannel).

And if we’re going to look at grunge, we must not skip over our grunge godfather Kurt Cobain. Rest in Peace our dear rock ‘n’ roll legend for you bestowed upon us an anthem fitting for funky basement shows full of indie bands trying to emulate your success — Smells Like Teen Spirit.

For those out of the loop, this iconic song is directly referencing the popular women’s deodorant, Teen Spirit. I know some of us may have thought the song was a weird ass anecdote for youth… but it’s not.

Cobain dated a sweaty musician by the name of Tobi from the band Bikini Kill in the 90’s. She wore a lot of Teen Spirit and her bandmate, Kathryn, thought it’d be funny to write ‘Kurt smells like teen spirit’ on his apartment walls. — Chanell Noise


19. A Tribe Called Quest (ft. Leaders of the New School) – “Scenario” (1991)

One of my favorite music videos of all time is Scenario from A Tribe Called Quest featuring Busta Rhymes. It’s in my top five for sure; when I first saw it on MTV Jams back in the day, I thought the tv broke.

I was torn — should I get my dad or keep messing with the input settings on his large flatscreen? The song itself was so nuts, I just waited the mess out. 

By the time Busta Rhymes came on the screen I had reconciled the music video was the cause of the confusion and switching textures. I was pretty familiar with Busta Rhymes having and starring in epic music videos at this point in my life.

And coming up in the epic era of conspicuous-consumption rap cast my reverence for A Tribe Called Quest as uncommon. Undoubtedly before my time, I spent a lot of time working backwards in the group’s discography the older I got. Their album The Low End Theory would end up being one of my first CDs and “Scenario” would be one of my first ripped songs I downloaded for my Zune (sorry guys!) — Chanell Noise


18. Björk – “Hyperballad” (1995)

One of the more stunning moments in a catalog absolutely brimming with them, this Post highlight finds our Icelandic wonder exploring a dreamscape in which the narrator extricates pieces of her life over a cliff and explains to her lover that she does this “So I can feel happier / To be safe up here with you.” The rather macabre lyrics—the narrator ponders what it might feel like to throw herself from the cliff—don’t inspire overwhelming darkness thanks to Bjork’s sensational vocals and a Aphex Twin-indebted shuffling acid house beat that is combined with a string section conducted by Brazilian conductor Eumir Deodato to jaw-dropping effect. Perhaps the best distillation of Björk—if you had only one song to play for someone who’d never before heard the queen, this would most likely be it—“Hyperballad” sounds as thrilling and original today as it did in 1995. — Donovan Farley

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17. OutKast – “Spottieottiedopaliscious” (1998)

Within “SpottieOttieDopaliscious,” there is much of what made OutKast one of the greatest hip-hop acts of all time. The languid spoken-word piece flows as smoothly as the Chattahoochie River that cuts through Atlanta and finds the philosophers Big Boi and Andre 3000 eschewing their usual verbal histrionics for a deeply felt rumination on being black and young in Atlanta in the late 90’s while backed triumphantly by the Southwest Dekalb High School Marching band. As long as I draw breath on this earthly plane I will never, ever forget the first time I heard the song: soaring on acid in the backseat of a friend’s car driving around Atlanta after skipping class in high school. Aquemini had recently dropped and we were in total awe. “This is a rap song?!” thought I while demanding the song be repeated (more than once). Existence seemed to open up around me. Everything seemed possible in that moment—for me, for art, for my future, for the world. I can still clearly picture exactly where we were in the city and even what the people with me were wearing, so vivid and impactful is the memory. Life and its many horrors (and also not being on LSD) have disavowed me of some of that wonder in the preceding years, but every time I re-experience the 7 minutes and 7 seconds of bliss that is “SpottieOttieDopaliscious,” I am joyously transported back to that moment when everything seemed possible. “That’s a beautiful thang, you dig? Now go and marinate on that for a minute.” — Donovan Farley


16. Pavement – “Gold Soundz” (1994)

The second single of Pavement’s 1994 record Crooked Rain, Crooked Rain, “Gold Soundz” has become a cult favorite among fans of ’90s indie rock despite its lackluster initial commercial reception. It never charted on Billboard and was overshadowed by “Cut Your Hair,” which peaked at 10 on the Hot Modern Rock Tracks chart. Pitchfork even named it their top song of the ’90s, citing that it “sounded like a memory in the best way.” Whenever I listen to this song, I can’t help but reminisce to days where my responsibilities were light and my afternoons were simply spent in my friend’s cars on the way to house shows. Malkmus gets you nostalgic here unlike anything else he’s written — Scott Hale


15. Sinéad O’Connor – “Nothing Compares 2 U” (1990)

If you haven’t noticed, the music industry has a way of weeding out outspoken women artists through labels of “controversial,” “difficult,” and “uncontrollable.” These labels don’t stick to people like Madonna because they know it’s all for the album cycle, but when you rip up a picture of Pope John Paul II on live TV, people — and most importantly, music business executives — know you mean what you say, and that’s a bigger problem than the widespread cover-up of child abuse in the Catholic Church. You know what she got for speaking truth to power? Forever shadow-banned from live televised performances, Joe Pesci reprimanding her with a light-hearted violent threat on the next week’s SNL, and Madonna repeatedly criticizing her.

“Nothing Compares 2 U” got Sinéad O’Connor on that stage, and it might be the most stunning break-up recording ever put to tape. I’ve never listened to Prince’s version, even though he wrote the song and made it first. Maybe like ripping up a picture of the Pope, it would feel a little sacrilegious. O’Connor’s version feels too holy to dishonor, though it’s certainly not just an old guy voted into power by other old guys in honor of something that probably doesn’t exist…but I digress. — Andrew Cox

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14. Belle and Sebastian – “The State I Am In” (1996)

There’s good reason that college rock and indie rock are often interchangeable terms. R.E.M. paved the way for a commercial breakthrough after finding footing on a college label, and Belle & Sebastian’s 1996 debut Tigermilk was originally a limited release of 1,000 copies by Stow College’s Electric Honey label.  “The State I Am In” is the first track off Tigermilk and became an instant classic following the record’s re-release by Jeepster Records in 1996.  As far as first offerings go, “The State I Am In” is about as perfect as it gets — displaying everything that made Murdoch and co. possibly the greatest band of the late ’90s. — Scott Hale


13. Lauryn Hill – “Doo Wop (That Thing)” (1998)

Lauryn Hill, sans-Fugees and coming into her own, wrestles with binaries in The Miseducation of Lauryn Hill, and specifically in “Doo Wop (That Thing).” To be educated, she must be uneducated first, then miseducated, then come to a form of truth. To be Lauryn Hill, she must come apart from her past, create an identity not informed by another remake, Pras Michel, or god-forbid, Wyclef Jean. She is a woman, first and foremost, yet she admonishes both her sisters and her brothers. She warns of the dichotomy between her people, while simultaneously investigating the collision and repulsion of old and new, doo wop and hip-hop, man and woman. She is a block party in Manhattan in 1967 and 1998, split-screen. She attacks materialistic values, hidden in a sneak-diss of Puff Daddy’s “bout the Benjamins,” of men who flaunt their money, and women who fall for it. She is anti-Jezebel, not because of promiscuity, but because of caricature, a black-and-white extreme, a familiar stereotype. That thing is not just sex, not just money, but the separation of the two. She is anti-separation, anti-binary, “only human.” She concedes, that much like “the sneaky, silent men” and the “hard rock when you really are a gem” women, she has been through “the same predicament”: everybody can be taken advantage of. Not offering judgement, instead she asks everyone, “How you gonna win when you ain’t right within?” This may be the first pronouncement of self-love, self-care, self-worth in hip-hop, devoid of division but embracing duality—a hyper-feminist and hyper-equal statement on identity, personhood, and growth—that thing cannot be named, not because it cannot be spoken of, but because it cannot be the only thing. — Lagnajita Mukhopadhyay


12. Beck – “Loser” (1993)

I once knew a girl who told me a fantastic story: her mom knew Beck when he was a nobody and even dated him for a while, eventually breaking it off upon the confirmation that he was a loser with no prospects. I have no idea if the story is true, and at this point I don’t care much, but I can’t help but think about experiences like that laying the foundation for Beck’s single from his third studio album, Mellow Gold. From coffee house gig loser to self-made success story, Beck stands to give us all a little hope that our own genius won’t go unrecognized for long, and that it can happen to us misunderstood losers, too. In fact, the oh so famous chorus of “Loser” was born from failure, as according to Beck, “When [Stephenson] played it back, I thought, ‘Man, I’m the worst rapper in the world, I’m just a loser.” — Scott Hale


11. The Smashing Pumpkins – “1979” (1995)

This song is like the part in the movie where the group of friends walks home as the camera pans out. This song is sad. This song is like fall. This song is nostalgia. 

The drum beats. 

This song is one I am not familiar with, but at the same time continues to play as I try to think of what it reminds me of. Much like trying to place the name of that person from that time and place in your memory. 

The guitar is strummed. 

Mine is of the color brown underneath dark green and every blue. I am writing letters home that won’t be received until I return there and we will read them in my driveway and laugh at my emotion. I realize how stuck I feel. I realize I can’t remember. 

But we’ll be okay because we have to until we can’t. 

The song plays out.

— Sadie Burrows


10. Pulp – “Common People” (1995)

What’s great about “Common People” and keeps it from being a rich/poor binary class argument is that the song’s just about two people: the speaker and the rich art college student. Through them, Jarvis Cocker builds a world and an era-defining anthem for everybody. Britpop was a musical movement for the people, by the people and somewhere amidst Blur’s and Oasis’ massive popularity, that messaging was lost to tabloids and awards show squabbles, i.e. upper class artist concerns. Pulp brought things back down to Earth but still with the songwriting scope to feel larger than life. For that, it’s timeless and belongs in the upper echelon of British epics alongside “Baba O’Riley,” “Blue Monday,” and “Heroes.” — Andrew Cox

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9. Nas – “N.Y. State of Mind” (1994)

Ah man, it’s not uncommon for classic ’90s tracks to also have immense cultural significance. Hip-Hop as a culture is so young, yet so rich. Reveling in the even richer and nuanced tapestry that is the African American experience, and Hip-Hop holds a mirror to Black life. The ups, downs and everything in between is Hip-Hop — rap is a tool to tell this story and Nas is an artisan.

N.Y. State Of Mind is in a realm of its own, much like New York City. The Black experience in America is unique; the Black New Yorker experience has an even greater distinction that has filled up countless books, movie screens and, most notably, music.

Nas, a New York-native, came up in a golden-era for rap. East Coast-based emcees were basking in the birthplace of the movement — telling their stories. Each emcee unknowingly acting as an architect for a future where rap knows no bounds, no limits.

The shit that Nas raps about is hard. It’s cold and possibly too crass for some. Yet his wordplay created a space for the world to play — “N.Y. State of Mind” serves as the design for how to introduce oneself and one’s stomping grounds. — Chanell Noise


8. Mazzy Star – “Fade into You” (1993)

“Fade into You” is an iconic staple of ’90s alt from the dream pop pioneers Mazzy Star. There is quite possibly no song as associated with forlorn yearning and quiet angst as the Santa Monica band’s most popular song. Although Mazzy Star’s music was never featured in the original run of Twin Peaks, it’s hard not to imagine Mazzy Star standing in for Julee Cruise on stage for some of the show’s most iconic moments. Either way, they’re forever connected in my brain, and it’s surprising that Mazzy Star’s music wasn’t chosen for the show’s return as one of the closing Roadhouse acts — too predictable perhaps, given that “Fade Into You” is already the dream pop soundtrack go-to. — Cheyenne Bilderback


7. Geto Boys – “Mind Playing Tricks on Me” (1991)

“I sit alone in my four-cornered room staring at candles” — a lyric from Snail Mail, Julien Baker, or the first three seconds of Geto Boys’ greatest contribution? Anxiety and mental health just wasn’t a hip-hop topic before Scarface launched into the first verse of “Mind Playing Tricks on Me,” and this type of lyricism still feels like a needle in a haystack. Geto Boys — with Bushwick Bill having barely survived a self-inflicted gunshot wound — were in more than just a reflective mood; they deconstructed the unemotional braggadoccio persona of hip-hop to reach a deeper, truly gritty account of what it means to be Black in America. When Scarface comes back around for verse three, he digs deeper by connecting his fractured relationship with God with the woman he loves and how it affects taking care of his son. When Isaac Hayes’ guitar sample plays in the hook, it allows you time to ruminate within a loop as disorienting as the lives of everyone in the song. — Andrew Cox


6. Aaliyah – “Are You That Somebody?” (1998)

For all intents and purposes, Aaliyah’s career truly kicked off when she began working with Timbaland. Timbo not only came with two songwriting geniuses – Missy Elliott and the late Static Major – but his late ‘90s production work betrayed how voracious his taste happened to be. “Are You That Somebody?” sounds like a glimpse of the future melted down in a ‘90s funk grinder. Here’s a shortlist of everything included in the production: staccato guitar, a pure rubber bassline, drum programming that sounds indebted to U.K. drum-and-bass, distorted adlibs, beatboxing and yes, a crying baby. It’s enough to throw off even the most seasoned of singers. Thankfully, Aaliyah thrived as a singer who operated on a plane much different from conventional R&B. When other singers would go for an exuberant delivery, she played it close to the chest – opting for an understated performance that helped “Are You That Somebody” feel more like a transmission from an alien world. Only four years later and Aaliyah and Timbaland would fashion R&B to be much closer to their image, but we have yet to hear anything on the level of “Are You That Somebody?” – or at the very least, more songs with prominent baby samples. What the heck? — Jibril Yassin


5. Wu-Tang Clan – “Protect Ya Neck” (1993)

“You know what I want to hear right? I wanna hear that Wu-Tang joint.”

Many of these songs on this list elicit an emotional, perhaps a physiological response. You remember where you were when you first heard a song or you have funny memories attached to these classic hits. Either way, there are few songs that bring forth the nostalgia like anything Wu-Tang Clan made.

I first heard Protect Ya Neck in my childhood living room in ‘98. I have hazy memories, brown at the edges from toddler-amnesia and time. My mom was doing some spring cleaning and my dad had just gotten a new stereo system complete with a cassette-player and 5-CD-disc player.

My parents were younger folks, my mom and dad having me at the youthful age of 19 and 21 respectively. The consequence of what must have been an eye-opening, yet rewarding experience for them was my expanded hip-hop vocabulary. I swear (it’s in my baby book, ask my momma) my first words were Wu-Tang. — Chanell Noise


4. Dr. Dre (ft. Snoop Dogg) – “Nuthin’ But a ‘G’ Thang” (1992)

I could tell you how influential this song is, and how it reinvented — or at least signaled — the new era of rap in popular media (Rap is Pop, Pop is Rap). Maybe I could go through the objectively great qualities of the song, from the beat to Snoop’s first verse to how it compares to the rest of the classic The Chronic.

But take a step back with me. Isn’t it just a 4-minute song that checks all the boxes of what “great” music has to be? Is it hyped up and revered to the point where it’s more statue than song — something to be viewed at from behind a velvet rope rather than heard at a party? To all that I say, press play and “just chill ’til the next episode.” — Andrew Cox

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3. Aphex Twin – “Windowlicker” (1999)

Aphex Twin is the greatest artist of the ’90s, right? Pavement, Björk, Radiohead, and Nirvana are fine answers, but being the leader and curator of a whole new brand of electronic music, reinventing himself with every year, and offering visual accompaniments that rank up with the best cinematic displays of body horror kinda seals the deal. “Windowlicker” is his final epic of the decade, and it represents a brief moment where difficult electronic music could be normalized, at least in the UK. It was a top-20 hit, received a Brit for Best Video, and was named NME’s best single of the year. The song is an absolute barn-burner with elements of French Touch that Aphex Twin utilized to upend its simplistic romantic view. I still catch little mysteries down in the mix when I listen on different speakers. Someone could probably take the most melodic elements here and create your standard club hit of the time, but of course, it wouldn’t be Aphex Twin if it wasn’t taken a thousand steps beyond where it needed to be. — Andrew Cox


2. The Notorious B.I.G. – “Juicy” (1994)

The Notorious B.I.G. is the greatest to ever rap, and “Juicy” is where it all came together. Say any line here in the right setting, and you could have a crowd singing the rest of the song in unison. It’s as much a classic rags-to-riches story as Citizen Kane; the comedown happens outside the song’s lyrics. It might be impossible to pick the best of the three perfect verses here, but the last one can still stun you in wondering how someone can construct so many lines that melodically and that forceful — think about how he says “sofa” or “lounging” and if you say those words like Biggie from now on. The song even brought back a hidden gem in its sampling of “Juicy Fruit” by Mtume. “It was all a dream” — go ahead and fill in the rest. — Andrew Cox


1. Radiohead – “Paranoid Android” (1997)

In my senior year of high school, my youth symphony performed a string arrangement of “Paranoid Android,” allowing me to understand the piece on a much deeper level than at first listen. I had never worked on a rock piece with an orchestra, and it forced me to study the song more than I normally would have. In a way, it brought me closer to any Radiohead song than I have ever felt. I had never spent hours analyzing and practicing one of their songs, and the experience gave me a special peek into the complexity that goes into each and everyone of their compositions. The majority of the song is in 7/8, creating an agitated feel and an unresolved sound. It’s incredibly advanced compared to past Radiohead compositions, with much more daring harmonies and musical strategies. With four sections, the song is almost like a tiny classical composition, with recurring themes expressed through variations and differing moods, all finally resolving at the conclusion. The fourth section listens like a giant exhale from Yorke, the exhaustion coming through in his delivery. His past work doesn’t hurt the performance, if anything it strengthens it—a reminder of the band’s dedication to creating new and innovative works of musical art. — Virginia Croft