The 40 Best Songs of the 90s: 40-21

The 40 Best Songs of the 90s: 40-21

Wrestle with Jimmy and grab your Zima for the first installment in our 40 Best Songs of the 90s.
fiona apple in our 40 best songs of the 90s cool hairstyle

We had to consider that the nineties entered a new phase as it reached its close and that right around 1998 things got weird. Bill Clinton’s impeachment, Columbine, and the annexation of Hong Kong seemed to challenge the discourse and make people reconsider their politics. Most of all, the collective paranoia of a fatal computer bug at the dawn of the new millenia and a general mistrust in new tech seemed to influence all of pop culture. So, we didn’t rank anything after 1997 which will be saved for a separate list.

We will be releasing this in three parts: 40-21 on Monday, 20-11 on Wednesday, 10-1 on Thursday.

If you disagree with our choices, just pretend it’s the 90s and meet a friend at the coffee shop so you can discuss it…pretentiously.

the introduction

20-11: rel. February 23

10-1: rel. February 24

40. 2pac: “Hit ‘Em Up”

[1996, Death Row]

Prison changed Tupac Shakur.

He was angrier, more defensive of his stances in interviews, and under larger threats. He claimed “the whole world owed him an apology” for convicting him of sex abuse and compared himself to Kurt Cobain. Upon being bailed out in exchange for his signing with gangsta rap mega label Death Row, violence became a central part of Shakur’s reputation. Tragically this would be the fatal flaw that his superstardom now predicated on a gangster persona, could not exist without. This was not the only part of his identity, yet a very important one. He was talented, he was photogenic, he was socially conscious, he was charismatic, he was convincing, he had stage presence, he could act, but none of these existed alone to put him on the lips of every person in the culture.

Tupac was dichotomous to the point of being incredibly complex. As profound as he was dangerous. Two sides of the coin that his audience was constantly presented with. “Hit ‘Em Up,” one of the best examples of Tupac’s multi-facetedness wasn’t just a diss song, it was a full on declaration of war. Not so much a chess move as a jailhouse stabbing, a caloric-tempered Sun Tzu-style provocation under the world’s eyes. Even its featured players Hussein Fatal, Yaki Kadafi, and E.D.I. Mean were named after dictators.

A product of uncompromising confidence and caustic anger, “Hit ‘Em Up” would work almost purely as an artifact in hip hop history. Its mixture of hatred, rage, ignorance, emotional release, and violent intent would culturally reverberate through hip hop for years to come. Tupac body shames the swagger jacking Biggie, compares him to a dog, and claims to have had relations with his wife with an unflinching seriousness. It’s glorified in how uncomfortable it can make you feel, but it’s by no means a celebration. Pac’s revealing of Biggie as someone who was once his friend gives a vulnerability to his battle cry as one of deep betrayal.

“Hit Em Up” also exists as a demonstration of Pac’s unfiltered talent in one of his most productive periods. Knowing he had to perform at an optimal level in order for any of this to work, he mobilizes the best of his arsenal: articulate ferocity, raw aggression, emotional vulnerability, innuendos, rap singing... Tupac’s voice and his projection on the microphone is used here perhaps to its best ever advantage, with an internal fire that made him a more valid candidate in a sparring match like a rottweiler to Biggie’s basset hound. Still even without its voice, “Hit Em Up” is so bold it even feels untamed on paper. - AC


39. R.E.M.: “Man On the Moon”

[1992, Warner Bros.]

Michael Stipe is one of the more introverted stars of the era, but his understated nature never prevented him from an active social life behind the scenes. He was a direct influence on many musical powerhouses of the decade, including Kurt Cobain and Thom Yorke, but his friendships with artists in other disciplines were just as integral to developing his creative vision. Pioneering alternative comic Andy Kaufman was one of these important friends, and he carved himself a unique position in the zeitgeist through comedy much like Stipe did through songwriting.

“Man on the Moon'' is a personal tribute from Stipe to Kaufman, and it’s written with the same enigmatic irreverence that colours each of their respective aesthetics. The lyrics are incredibly cryptic, and contrast conspiracies about the moon landing with assertions that Kaufman faked his own death. They function almost like an auditory Rorschach test, with many fans ascribing their own emotions and interpretations to the song’s ambiguous lines. Its scope is also eerily predictive of the internet age, as it navigates ideas of misinformation and post-truth with a distinctly postmodern sense of detachment: “Let’s play Twister, let’s play Risk/yeah, yeah, yeah, yeah / See you in heaven if you make the list.” Almost every line is tongue-in-cheek, with Stipe drawing parallels between St. Peter and the Parker Brothers. However, the song’s playfulness doesn’t undermine its sincerity, as the focus is repeatedly brought back to Kaufman. It’s contemporary and enduring success is a testament to the friendship that inspired it. – VUJ


38. Aphex Twin: “Xtal”

[1992, Apollo]

Richard D. James had always created music that offered some unique authenticity to the electronic music landscape. Perhaps it was due to his methods; from his experiments with computers and synthesizers at a young age to his early embrace of techno, that the musician always had a knack for being ahead of the curve. His first album, recorded between 1985 and 1992, was a homemade affair and a true DIY effort. Although titled Selected Ambient Works 85-92, many of the songs are based around dance music beats. The ambience seems to come more strongly from the melodic aspects of the songs and opener into James’ world, “Xtal” is no exception. And the results of the combination of those styles? An authenticity that electronic music had not seen before.

“Xtal” begins with a cymbal rhythm played on thin, fluttering drum samples. Once the soft kick drum starts hitting every beat, the pulsing melodic synths bubble their way to the forefront. It’s light, groovy and airy, especially when the wispy vocals appear to sing but only two notes. Soon, the drums shift to a much grittier and more interesting beat defined by a newly introduced snare drum, while the rest of the song stays intact. It’s a technique that RDJ would go on to employ to much success later on in the decade (see “Alberto Balsalm”). As the song fizzles out into a synth pad’s three descending chords, RDJ perfectly invokes the feeling of accomplishment one gets from leaving a good night at an underground dance club as the sun begins to rise in tranquillity…the perfect comedown.

“Xtal” is a vital track, because for many, it was their introduction to Aphex Twin, as well as left-field electronic music in general. While Aphex went on to continuously challenge his audience, this track is what led fans through the door initially. Proof that something can be accessible, while still pushing the envelope. - NCII


37. Spice Girls: “Wannabe”

[1996, Virgin]

If you’re a real Spice Girls fan like myself, upon hearing Mel B shouting in “Wannabe,” you can only picture how the Spice Girls assumingly hoped we’d forever remember their defining song: through the flashback scene in Spice World. We see the Spice Girls pre-fame, in less flashy getups, and as the last customers in a local diner performing for its indifferent innkeeper (who opts for jazz instead). Remember? Sporty Spice has a doo rag and Baby’s wearing her oversized V-neck? Mel B sings into the saltshaker and Mel C back-handsprings…ring any bells? Crucially, the girls are portrayed in their adolescence as lighthearted, impressionable, and maybe even a bit naïve before the fun of performing the song together makes it easier to embark on their ambitions. But besides reinforcing nostalgia, which continues to be experienced either through generations of people choreographing their very own guerilla dances to it or enjoying the song in a club a decade later, “Wannabe” presents a new age for the female pop group.

Spice Girls brought a new mantra summed up by their declarative coming out party: friendship and girl power over everything else. ESPECIALLY ANY MALE BEING, whom here are kept at a distance to a number of conditions. It was secretly revolutionary in a way, despite being incredibly populist: “Wannabe” became the biggest song in about 40 countries which in turn helped sell 30 million copies of Spice. Put it on now and the balance between its confidence and its tackiness, which by all means has to be embraced, is everlasting. Its undeniable dose of energy could have only come from five upbeat young women in the UK 90s has retained its spark. - ME


36. Weezer: “Say It Ain’t So”

[1995, DGC]

Weezer is lame. Weezer is male-manipulator music. Weezer is problematic. It's not that time has been unkind to their catalogue. If TikTok is any indicator then Weezer and their brand of nerdy bops are just as relevant with Gen Z as they've ever been. The better adjective for Weezer would be "recontextualized." Time has changed since The Blue Album debuted.

Where having a garage full of X-Men comics was once a dirty little secret among a niche subculture of outcasts, nerd culture has now been repackaged by Kevin Feige to appeal to the Chads and Staceys. Weird colloquialism? Maybe, but that brings us to our next problem. Weezer has been rebranded as proto-incel music. Their holier-than-thou approach to intellectual property, mixed with a bizarre sense of sexual frustration and entitlement, has made Weezer a strange cocktail to stomach for a more socially conscious generation. People still want to hear Rivers Cuomo ride his surfboard through a fictional (?) flooded America… but unfortunately that experience comes with some baggage.

Luckily, "Say It Ain't So" doesn't come with any of that. Featuring Weezer at their most honest, "Say It Ain't So" is a heartfelt emo cut predicated on a relatable theme: familial trauma. Thinking that his parents' marriage ended due to his father's alcoholism, "Say It Ain't So" spawned from Cuomo finding a beer in the fridge and catastrophizing that his mother and his stepfather's marriage would end the same way. There's a Gothic quality to the track, the ghosts of Cuomo's past haunting him as he roams his childhood home.

It feels like the same man who'd brag about his Dungeons & Dragons set; "Say It Ain't So" is still about nostalgia. But where much of The Blue Album is connected to the pleasure of memory, its best single is more concerned with its pain. "Say It Ain't So" has an emotional potency that makes it timeless and, more importantly, context-proof. - JM


35. Natalie Imbruglia: “Torn”

[1997, RCA]

There’s a handful of pop songs that everyone loves, but few people vocally defend. Not to be confused with the guilty pleasure, the kind of song whose infectious catchiness and over-saturated airplay often result in unfair accusations of artistic superficiality. Some key examples from this era include “Lovefool” by the Cardigans, “Stay” by Lisa Loeb, or even ”I Love You Always Forever” by Donna Lewis. They each have their own organic appeal, but few of them were as ubiquitous or underestimated as Natalie Imbruglia’s “Torn.”

Feminine vulnerability is the key thread that connects all of these popular classics, so it’s easy to see why critics dismissed their value before the turn of the millennium. If “Torn” was released today, Natalie Imbruglia would be releasing a Jack Antonoff-produced ‘Best New Album’ by the end of the year. The song meditates on finding disappointment in infatuation, and it tells the story over a simple pop beat that keeps the focus on Imbruglia’s earnestness. While the lyrics read like a carefully written diary entry, her tongue-in-cheek cadence (“you don’t seem to know or seem to care what your heart is for”) balances out her more earnest vulnerability (I’m cold and I am shamed lying naked on the floor). It’s raw without being over-indulgent, and can be enjoyed as mindfully (or mindlessly) as the circumstances call for. What more could you want from a pop song? - VUJ


34. Blind Melon: “No Rain”

[1993, Capitol]

If there ever was an award for the most underrated, overrated song of all time, “No Rain” would be a serious contender. The kind of populist anthem that can unify people of markedly different tastes, and one of the few Top 40 mainstays that truly never overstayed its welcome.

Like most of the radio favourites of its time, “No Rain” is undeniably catchy. However, its light and cheery sonic palette masks a darker lyrical focus and foreshadows the tragedy that would halt the band at the height of their fame and potential. The song is mostly a meditation on listless ennui, but its most famous verse hints at the depression that several of the bandmates were experiencing: “and I don’t understand why I sleep all day, and I start to complain that there’s no rain.” It illustrates the contradictions of living with the affliction, and how it transforms your personality so gradually that you lose the awareness to consciously resist its influence. The lyrics are simple but they resonate deeply with Shannon Hoon’s honest delivery who was in and out of recovery throughout Blind Melon’s history, but tragically died of an overdose shortly before the release of their sophomore album. In hindsight, the success of the song seems almost like a misinterpreted warning.

“No Rain” has endured as one of the decade's most affable hits, but its success is still darkly underscored by the tragedy that followed. Despite proving their mettle as indie-pop progenitors, Blind Melon’s efforts never crystallised into a notable full-length album and they never found a replacement to match Hoon’s effortless charisma. The enduring appeal of “No Rain” is very much a testament to his peerlessness. - VUJ


33. Shania Twain: “That Don’t Impress Me Much”

[1997, Mercury]

So you’re Brad Pitt? Hate to break it to you, but that still won’t impress Shania Twain…well maybe now, but certainly not in 1997 when Shania was arguably more famous. Apart from being a cheeky dig at self-absorbed men, and a larger lament on the trials of dating, what is impressive (unlike these scumbags), was the massive crossover success Shania Twain achieved as a modest country singer from Windsor into a new pop queen, based not only on her likability, but sensibility.

On first listen, “That Don’t Impress Me Much,” the seventh single from the game changing Come On Over (an album with 12 singles) seems to diverge from country to pop, and thematically from the romanticism of Shania’s earlier music. If we take a closer look, we see hints of a longer for something more, for someone to keep you warm on “long, cold, lonely” nights which holds itself in line with the more tender love songs in her early canon. Look beyond the song’s initial cynicism and receive a story of a heroine still searching for love despite having to kiss many frogs. It’s a perfect combination of country sass and storytelling, but with a redefined pop sensibility for the nineties. Culturally, it also solidified a new path for future country artists. Seeing a former country star in a leopard print suit and cape, wandering the desert, singing clever words about dating troubles, and traversing new pop territory feels like a trip or a fever dream of the best kind possible. You certainly don’t get 1989 without 1997. - TV


32. Rage Against the Machine: “Down Rodeo”

[1996. Epic]

Though proletarian revolt might be the “cool” new sticker to slap on your brand in the Pandemic-era, the rights of the downtrodden and the disenfranchised were not the concern of White America in the nineties. Post-Cold War fairy dust had whisked privileged Americans into a blissful sleep. While Rage Against the Machine were trying so desperately to wake up their fellow countrymen, “Down Rodeo'' finds frontman Zach De La Rocha wrestling with the possibility that the system may be too entrenched to overthrow. Evil Empire’s cover art painted a maniacal, jersey-toting teenager with an ominous smirk and an art style that resembled Big Brother propaganda. But where Evil Empire resigned itself to the American reality, the violence of its centrepiece “Down Rodeo” felt more like catharsis than purposeful action.

As Tom Morello's creative guitar work gives the murderous journey its direction, Zac rolls down Rodeo Drive with his weapon of choice—a wealthy neighborhood that was left untouched by the ‘92 L.A Riots. Over the course of the song, he criticises NAFTA as an excuse for the exploitation of Mexican workers, reflects on the rippling effects of the War on Drugs, claims that freedom of speech does not exist in America, and demands that workers seize the means of production. Aside from their consistent references to punk, metal, hip hop, and funk, it’s their dense political subject matter that would make Rage so influential to succeeding groups like System of a Down, Parquet Courts, and Run the Jewels. Similarly, what makes “Down Rodeo” so troubling is how current it feels. The track ends with a pessimistic assertion that our attempts to revolt may just be a “dance" that fails to bring effective change to our core problems. It’s a claim that has yet to be proven wrong. - JM


31. Pavement: “Range Life”

[1995, Matador]

The instantly recognizable opening twang of Pavement’s “Range Life” is playful, fun and a fine entry into the band’s corpus. But what you might miss is that behind its freewheeling exterior musing upon America’s charming heartland, is a soulful reckoning of youthfulness at the end of youth. Its introductory verse accepts the end of “the glow, the scene, the stage” and “sad talk” and acknowledges the responsibility of “paying your dues before you pay the rent.” In other words, how does one direct one’s life when one is old enough to repay, but young enough to sell?

And don’t mistake “Range Life”’s infamous winking jabs at Smashing Pumpkins and Stone Temple Pilots as beef. These hazy quips express not ill-will, but a real sense of disillusionment with the rockstar life. As exceptional as the Smashing Pumpkins (and to a lesser extent STP) were as a musical force, they were quick to elevate their angst to stadium status and revel in it even as they symbolically turned away (see Billy Corgan smiling politely in the Simpsons episode “Homerplooza”). Pavement were too self-aware and ironic to make themselves a spectacle. Instead of holding the audience in the palm of their hand with “Disarm,” the audience’s hands hurled dirt clods in the absence of Pavement’s willingness to deliver an anthem.

But there lies the wonder of “Range Life.” It is an anthem of wrangling life’s branching possibilities, as sung by its great predecessor, the Beatles’ “You Never Give Me Your Money”: “But oh that magic feeling/ Nowhere to go.” Incomplete crimes, fading Walkmans, drug abuse … Pavement takes responsibility for all of it even as they make room to dream in the pastoral myth of home on the range. So much for slackers. - BH


30. The Breeders: “Cannonball”

[1993, 4AD]

Kim Deal is really cool. This has been obvious since the initial formation of the Pixies, but became even more apparent when her distinct songwriting and stage presence erased the stereotype of the bassist as filler. Despite the overwhelming success of the Pixies, it was unsurprising that she would eventually shift her focus to The Breeders, a project that was more directly rooted in her creative vision. Their first album, Pod saw critical and artistic success, but it wasn’t until Last Splash when they truly connected with the mainstream. The entire track list is memorable and a personal favourite of Kurt Cobain, but “Cannonball” made the biggest splash in the mainstream for a few key reasons.

Deal was responsible for some of the most iconic basslines of the eighties, (“Here Comes Your Man,” “Debaser”) but evidently saved her strongest effort for the following decade. The opening of “Cannonball” sounds like an audio time capsule from 1993 with Deal’s distorted vocals and iconic bassline immediately grounding you in the effortless cool of the era. The following bridge and chorus are anthemic in their execution, and the various silent pauses build a degree of anticipation that distinguishes the song from other contemporary alt rock classics. While the influence from Pixies and the Riot grrrl movement are traceable, there’s a distinct charisma that separates Deal and The Breeders from the wider labels used to describe these genres. “Cannonball” is the most accessible example of their appeal. - VUJ


29. Alanis Morrissette: “You Oughtta Know”

[1995, Maverick]

The empowering expressions of “You Oughtta Know” still really work now as they assumingly did in the nineties, when these were the dominant emotions: betrayal, large waves of anger and relief, uncomfortable moments of calm, having an inconsolable episode. Alanis Morrisette’s vehement “You Oughta Know,” with its quiet wicked-tongued verses and a chorus that feels like you’re being hit by a flood presented a catharsis that was blinding and quick. Alanis stated, “I wasn't aware of what was coming out of me. I'd go into the booth when the ink wasn't even dry and sing. I'd listen the next day and not really remember it.” In many ways, this represents the singer songwriter’s refusal to be categorised in terms of genre and dedicating herself totally to authentic emotional expression.

Regardless of the gossip that ensued about the subject of the song, Alanis is firm in its purpose - emotional release. In her own words, “...for women sometimes, we're told we can't be angry; we can't be sad, and we can't be…seventeen other feelings. [...] but I think I was really just devastated when I wrote that and it's a lot easier to syphon that through anger sometimes." David Coulier, most known for playing Joey on Full House, has the most substantiated claim to the track stating that Alanis ran into him while on the dinner date that was allegedly referenced in the song. Despite the fact that five more people have taken credit for being the inspiration behind the track, the song is entirely her own. “You Oughta Know” can fire anyone up about betrayal, real or imagined. - TV


28. Mobb Deep: “Shook Ones Pt. II”

[1995, Loud]

Sampling is one of the most inventive methods to create music, yielding an endless potential to manipulate infinite permutations of sounds. Given this magnitude of creative possibility, it’s remarkable that the clicking ignition of an old gas stove remains one of the most iconic samples in rap history. What’s even more impressive is that the iconic beat is only the tip of the iceberg when it comes to the value, impact, and legacy of “Shook Ones Part II.”

Most of the thematic content of the east-coast golden era is firmly grounded in social realism, but The Infamous captures the gritty reality of life on the streets to an unparalleled degree. “Shook Ones Part II” focuses specifically on the story of young men who lack the cold indifference needed to survive in the drug game, and buckle under the performative pressure of trying to be someone they’re not. The song is a harsh warning about the consequences of posturing in the criminal world (“think it through’) and is a masterful subversion of the contemporary myth that rap music glorifies and encourages violence. It also cemented the idea of a “shook one” in popular culture, with the character arc playing out through William in Immortal Technique’s “Dance With the Devil,” and Wallace in HBO’s The Wire to name a few. Avon Barksdale and Marlo Stanfield also endorse the song’s key lesson at several points throughout the series, reaffirming its timeless importance.

So much can be said about so many different aspects of “Shook Ones Part II.” The beat is historic, the raps hold flow and intelligence in equal esteem, and the authenticity of the subject matter is undeniable. Many rappers have found creative and financial success by embracing personas, but Mobb Deep were never interested in any deviations from the truth. The Infamous is an unfiltered glimpse into one of the most dangerous bubbles in American society, and “Shook Ones Part II” is the best example of Mobb Deep’s uncanny ability to sonically immerse you in that reality. – VUJ


27. Montell Jordan: “This Is How We Do it” 

[1995, Def Jam]

Montell Jordan was well connected. A fixture of the Los Angeles Christian community where he played piano for his church and a member of the Kappa Alpha Psi fraternity at the University in Malibu where he achieved a Bachelor’s in Communications. During his time at WTT network he got the attention of Janet Jackson and Shanice Wilson and his demo would quickly make it to the desk of Def Jam head Russell Simmons who signed Monty in 1995 with hopes for a #1 hit.

He delivered with “This is How We Do It,” a mega hit. The song sets its actions at a party on the westside of South Central L.A. on a Friday night; a good time shared by everyone on the block and truly nothing more. A paraphrasing of Slick Rick’s (who Jordan could emulate perfectly) more socially conscious and dark masterpiece on street life “Children’s Story,” itself a rework on Bob James’ “Nautilus.”

For something so novel, so goofy and so carefree, the song is very aware of what it wants to be and what’s around it. Jordan tells of his preference of a big black truck over a ’64 impala and notices an unofficial gang truce in the midst of the party. Crenshaw Boulevard and iconic brand Karl Kani are given colloquial abbreviations. It’s also weirdly un-horny for a 90s R&B jam, with little to no mention of sex and far more interest invested in the marquee event than whatever happens after. This is not exclusive to dance battles, stepping to the mall in a suit, and the glory of being in a big group of friends amidst celebration. OG Macks and Wannabe Players. It’s no wonder why the song’s omnipresence is used to sell everything from Hyundais to Swifters and holds more film credits than can be counted on one’s fingers and toes (which are too busy dancing anyways). The song’s popularity would provide Jordan, now a community worship leader and father of four no need for a second #1 hit. - AC


26. Oasis: “Live Forever”

[1994, Creation]

When Oasis released their debut album Definitely Maybe in 1994 it could be heard as a clear statement of intent. Opening track “Rock ‘n’ Roll Star” is almost embarrassingly honest about the band’s desire to be megastars (if only for a night) while much of the rest of the album presents the sound of a band that want to be seen as self-assured, most obviously in terms of who their reference points are (first two singles “Supersonic” and “Shakermaker” lean heavily on mid-60s Beatles output). But then there’s “Live Forever,” the album’s outlier and best track. It is one of key songwriter Noel Gallagher’s earliest creations, pre-dating the band’s formation, and it feels different from everything else on the album.

The emotional centre to the song belies its apparent indifference (“Maybe I don’t really want to know/ how your garden grows”) and presents instead a kind of longing for someone else to see the world with their same sense of hope (“Maybe you’re the same as me/ We see things they’ll never see”). And all those “maybes” in the song? That’s the mile of vulnerability that sets it apart from everything else on the album, and it’s what makes this track one of the greatest Oasis sing-along anthems in their catalogue. Because it’s so much easier to want to live forever when you’re one of thousands of people in a crowd singing it back to one of the greatest rock and roll bands of the 1990s. - JF


25. A Tribe Called Quest: “Scenario”

[1992, Jive]

If two sport superhero Bo Jackson doesn’t know what the scenario is after possibly running through all possible permutations, then who does? Well Busta Rhymes of course.

A Tribe Called Quest, seemed to carry a mission statement that separated the hardcore brazen attitude which dominated the locale at the time. It couldn’t be as simple as just blending jazz with rap, since these two styles of music were more spiritually similar decades ago than they are now, namely how people interpreted the word “cool.”

In terms of Tribe, perhaps the smoothest, coolest combo of all time, if The Low End Theory was Tribe’s crossover point, then “Scenario” was game 7. Through the synergy of its two lead MCs and the posse they would invite, in this case the underrated Leaders of the New School, their infectiousness forced you to inhabit their world. Together, both groups saw the rap movement as something more approachable than what the gangster rappers had envisioned and “Scenario” represented a push forward in their modus of upbeat Afrocentricity.

Sure it’s influential, taking the underground over, but it’s also just damn fun. The group’s innovative sampling combines the resolution of hard bop organist Brother Jack McDuff’s “Oblighetto” and Mitch Mitchell’s breakbeat that begins “Little Miss Lover” from Jimi Hendrix’s Axis: Bold as Love. Tribe explore the topsy turvy trife of New York life through batteries, Nytol sleep meds, Broadway Joe, Arsenio Hall, and the presence, or in this case absence of crime.

But rather shortly after its release, “Scenario” would become famous for another reason: the warm up imaginable for Busta Rhymes' long career. It’s more of a flare up really. Just 19 at the time and in full pursuit of the opportunity at hand, Rhymes comes in as the world’s greatest pinch hitter whose insides were made of fireworks. His verse is a constant chess match between order and chaos, knowing exactly when to deploy one or the other with a voice so animated it spawns multiple personalities. He becomes the unofficial first in a long rap tradition of a featured player using the god as a jump off point. Rhymes’ iconic verse flips the song’s major question branding the scenario at play to set up an era’s superstar. - KL


24. Beastie Boys: “Sabotage”

[1994, Ground Royal]

While the Beastie Boys have always had a sense of humour (reflected most notably through the entirety of Licensed to Ill), it was the release of this song and the accompanying Spike Jonze video that provided the band with the opportunity to showcase both their funny side and their extraordinary musical talents. 1992’s Check Your Head gave the group massive crossover success with the single “So What’cha Want,” instantly bringing the Lollapalooza audience into their fanbase, but it was the one-two punch of this song’s faux-70s cop show video and the rap-rock intensity of the lyrical delivery that made this song a hit. Using a combination of live instrumentation and DJ Hurricane’s beats, the Beasties had by now clearly established their own hybrid of punk rock and hip hop that made a song like “Sabotage” play just as well on a Best of East Coast Rap mixtape as it did on a Best of the Alternative 90s one. And although Jonze’s video didn’t reflect the lyrical theme or sound of the song, it demonstrated the adaptability of the Beastie Boys as performers, hinting at the extraordinary energy and masterful craftsmanship they would bring to their live performances. – JF


23. Fiona Apple: “Criminal”

[1997, Columbia]

Fiona Apple would go onto make far more sophisticated music, even more so introspective music, but nothing could ever be as clever as “Criminal.” It was the first thing to properly exemplify what Apple would represent first amidst a sea of new pop stars and later as an indie music lynchpin. “Criminal” by every measure seemed designed in its writing to demand attention.

Despite being 18 years old in 1996, Fiona Apple was the antithesis of the MTV generation. She wrote every word of her songs, she played an instrument, proficiently; her obsession with jazz and poets like Maya Angelou distanced her even further. She made candid music about her insecurities and her mental illness, she was admittedly anorexic and viewed food as a liability for the male gaze she was trying to shed; she was raped at the age of 12 in the home of her New York City apartment and talked about this event openly in interviews. As values and audiences transitioned, her attitude would be reappraised as powerful, largely affecting nearly every female artist that followed.

“Criminal” seemed written almost subconsciously as a response to her position in this growing pop music world of the late nineties. Its taunting allusions to religious imagery from the cleansing of sin to heaven and “the consequences at hand” provocatively toy with ideologies still prevalent at the time. “Criminal” was set loose abound a 1997 landscape that seemed like it held a manufacturing process comparable to McDonalds. The radio at the time featured “Wannabe,” Celine Dion, and Mariah Carey. The luxuries of Puff Daddy and the Family had a virtual stranglehold on culture and “MMMBOP” was near inescapable.

The video for “Criminal” which played constantly seemed to question whether itself was a vehicle for exploitation, but everything Apple did seemed to hold a mistrust in the corporate machine that she felt was hungry on exploiting basically everybody. “Criminal” not only is aware of this, it’s practically satire.

It’s written as a confession about making a mistake in a relationship and the double edged sword of female sexuality. The song has since become iconic for its characterization of the ostracization all women who speak their mind receive at the target of slut-shaming or record label marginalization or the sex that was omnipresent in marketing to youth. “Criminal” is paradoxically sarcastic as a response. To Apple this was merely a footnote; she wrote the song in 45 minutes to prove to her friends that she knew how to. Out came “Criminal.” Apple’s identity as a pouty, skinny, large-eyed, damaged girl who was being crucified for using the same lust to get what she wants that men were being celebrated for, so effectively expanded the conversation on sexuality in pop music, it accidentally became the machine that catapulted her to stardom. - AC


22. Jamiroquai: “Virtual Insanity”

[1996, Sony Soho Square]

To an almost comical extent, Jamiroquai became known for embodying retro motifs: funk, disco, lounge piano, big hats, dance moves, Ferraris. They meant for this to be totally unironic. Yet somehow, Jamiroquai’s mission statement to push an ethos that warns the present in concern of the future made them eternal. “Virtual Insanity,” which was up unto that point the closest thing Jamiroquai had made to a pop single, spares no barbs on the current predicament of humanity.

While Its sonic footprint is not only figuratively but literally indebted to the dance music innovated nearly twenty years before, Jamiroquai’s pure chops as an ensemble and the sharpness of their arrangements equal most groups of the era before. Zender and McKenzie’s rhythm section move through the song’s claustrophobic repetition like the world’s thickest slinky making its way down an infinite staircase. But while designed to be as bouncy and coloured as the party that was designed to distract us, “Virtual Insanity”’s lyric sheet reads pessimistic as hell. Jay Kay’s subject matter (himself predicting that he’d never get credit for the song’s thematic complexities) would have made him a deity on modern channels and the twitterverse.

Fascinated by the underground city of Sendai, Japan, which was bustling with energy and people while the city above ground laid dormant after being covered with snow, Kay imagines an inevitable dystopia full of third world debt & genetic engineering, overconsumption & new religions, and a humanity so dependent on & affected by technology that it can barely function without it

Reading this now it would appear that Jay Kay predicted the future, but here lies the mix of old and new school that Jamiroquai would so masterfully explore, a tightrope between preachy intellect and dead trends that would be embraced by a generation who considered these things their birthright. - AC


21. George Michael: “Freedom ‘90”

[1990, Columbia]

George Michael stepped into the 1990s by making it very clear that he no longer wanted to be seen as the same George Michael as the eighties heartthrob frontman from Wham!, or even the Aviator, jeans and leather jacket-wearing stud from his own debut solo hit album Faith. No, this was the new George Michael: singer, songwriter, musician, performer – but yes, still stunningly attractive. The single “Freedom! 90” from his second solo album Listen Without Prejudice, Volume One, cannot in any way be viewed as a stand-alone song: the accompanying video, shot by film director David Fincher through soft lenses, is inseparable from the track. And with good reason, as Michael uses the video and its visual symbolism to dismantle the iconic imagery associated with his 1980s’ persona, including the leather jacket, guitar, and jukebox that figured so significantly in his first breakout solo video for the song “Faith”. Also, Michael made the bold decision to not appear in this new video, instead having Victoria’s Secret models Linda Evangelista, Christy Turlington, Cindy Crawford, and Naomi Campbell lip-synch the lyrics to the song. It was a trend-setting decision, but as Michael’s lyrics in the song make clear “the way I play the game has got to change.”

While he doesn’t seem to regret his time in Wham! (“Heaven knows we sure had some fun boy… We were living in a fantasy”), he also believes that he deserves to be seen as more than just a pretty face (“Gotta have some faith in the sound… it’s the one good thing that I’ve got”). “Freedom! 90” has gone on to become an iconic song, popular both in the LGBTQ community and on the dancefloor, but it also represented a cultural moment when a pop star at the top of his game manipulated the system in his favour, told his side of the story, and started the new decade on his own terms. - JF


20-11: rel. February 23

10-1: rel. February 24




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