100. Silver Jews – “Random Rules” (1998)

When David Berman died in August of last year, indie music lovers young and old flocked back to American Water and specifically to its lead track, “Random Rules.” It’s the best example of why Berman had nothing but goodwill and reverence on his side; the deadpan humor and charming lyrics shine through on every line here. Berman, despite his sudden end, was a source of optimism in the face of crippling circumstances and depression. He still believed in the power of traditional songwriting, rhyming every other line as if they had to be. — Andrew Cox


99. Public Enemy – “Brothers Gonna Work It Out” (1990)

Public Enemy’s good-intentioned, often-muddled social activism garners the most attention from writers, but the Bomb Squad production might be their most lasting musical contribution. No other song in their discography displays quite the onslaught of riotous anger that “Brothers Gonna Work It Out” goes for. Two of the most sampled songs in history are used here (“Atomic Dog” and Melvin Bliss’ “Synthetic Substitution”) and the guitar comes from Prince’s “Let’s Go Crazy.” Public Enemy made more popular songs, but they never sounded bigger. — Andrew Cox


98. Mary J. Blige – “Real Love” (1992)

Mary J. Blige’s “Real Love” appeared on her debut 1992 album What’s the 411? and was Blige’s first top ten Billboard hit and second R&B #1. She would finish the decade with 13 US R&B top 10 hits — more than Boyz II Men, Jodeci, Aaliyah, TLC, and nearly every other artist you can name. The Notorious B.I.G. appears on the hip-hop mix and this was before he released any solo work. The song has a wide universal theme (how many songs are also titled “Real Love”?) with maybe the catchiest melody of her career. When Blige sings, “I’m searching for a real love,” who cannot relate? — Cheyenne Bilderback

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97. Guided By Voices – “Game of Pricks” (1995)

How can a song that barely lasts 90 seconds remain captivating after hundreds of listens? Robert Pollard cracked the case with his signature song — one of the seemingly millions he’s wrote and put out into the world. You can study the song’s structure like a Max Martin pop formula and find it’s not really that unique; it’s just executed perfectly. “Game of Pricks” is just lo-fi enough to fool you into thinking it’s a bedroom recording only you stumbled upon. — Andrew Cox


96. Angelo Badalamenti – “Twin Peaks Theme” (1990)

In my first semester of college, I discovered the wonder and weirdness of Twin Peaks. It hooked me immediately, its opening credits panning over an eerie Pacific Northwest town, with all its beauty and familiarity. Twin Peaks had its parts that every town had, the interesting characters and recognizable problems. However, its music painted an irresistible soundscape. Angelo Badalamenti’s theme is haunting, oozing with soothing synths but leaving a sense of urgency in its last measures. Tuning in for an episode was an escape from my own environment, the theme enveloping me as I succumbed to the mystery of Twin Peaks. — Virginia Croft


95. The Notorious B.I.G. (ft. Puff Daddy & Mase) – “Mo Money Mo Problems” (1997)

Nobody has ever quite had the chart success of Sean “Puff Daddy” Combs in 1997, but, as we all know, it came at a price. In March of that year, The Notorious B.I.G. was killed in a drive-by amidst the West Coast-East Coast hip hop feud. Puff Daddy’s Bad Boy Records mostly rose and fell with Biggie’s success, and his death catapulted his legacy and new album Life After Death to heights that few rappers have experienced. “Mo Money Mo Problems” was the most pop-ready choices from the album with the Diana Ross sample and reached #1 on the Billboard charts for two weeks. This followed Puff Daddy’s “I’ll Be Missing You” which honored Biggie and spent 11 weeks at #1. The classic opening verse from Mase also signaled who would be Bad Boy’s next star. — Andrew Cox


94. En Vogue – “My Lovin’ (You’re Never Gonna Get It)” (1992)

When we examine “girl groups” (for want of a better term) throughout music history, the sometimes underappreciated En Vouge are the clear bridge between the Supremes and their ilk and Destiny’s Child. En Vouge were immensely talented, strong, independent black women who owned their sexuality and unabashedly and unapologetically expressed these facets of themselves in a way that can only be described as powerful. “My Lovin’ (You’re Never Gonna Get It)” sees them crystallize all that in one of the best R&B singles of the decade. Maxine Jones and Dawn Robinson just absolutely go HAM on their vocal turns, which are all empowerment and righteous fury, over an arrangement built, appropriately enough, around a guitar sample from James Brown’s “Payback.” Hell hath no fury like wildly talented women scorned. — Donovan Farley


93. De La Soul – “A Roller Skating Jam Named ‘Saturdays'” (1991)

De La Soul took their critics’ words to heart for their second album De La Soul Is Dead. The album’s skits — led by the skit grandmaster himself Prince Paul — revolve around people who find a De La Soul cassette tape in the trash and proceed to criticize the album as it’s playing. It’s a badge of honor for the hip-hop outsiders to take on haters and belittle them through shining a spotlight on them (OutKast would follow suit on Aquemini with a similar skit). The album’s lead single was as D.A.I.S.Y. as the 3 Feet High and Rising material with light-hearted samples and the goal of going for a vibrant roller skating joint. It signaled a bridge to the broken flower pot on the album cover. — Andrew Cox

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92. Radiohead – “Let Down” (1997)

There’s a consensus for the best song off OK Computer (stay tuned) and the biggest song with the iconic music video is “Karma Police” (#255 here), but Radiohead’s mainstream peak just can’t be reduced down to those two songs. “Let Down” is the most straightforward track on OK Computer, and that’s where its power lies. The melancholic beauty of The Bends is left intact but expanded to this awe-inducing glacial sculpture. The layering of vocals by the end is classic Pet Sounds and Abbey Road with quite possibly the biggest emotional high of their career. — Andrew Cox

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91. Ghost Town DJ’s – “My Boo” (1996)

Ghost Town DJ’s are a one-hit wonder, and many people know their song “My Boo” without even knowing who made it. It’s best known as a the “Running Man Challenge” on Vine (I don’t know what the fuck that means — I’m just reporting the facts). Due to the trend, “My Boo” charted higher in 2016 than in 1996. The song — the group’s only single — is basically a standard R&B song that is made into a classic through its Miami Bass percussion, which by this point had fallen off as a trend and was rarely used for radio singles. In an era of pop music where melodrama and balladry reigned supreme and R&B music lacked a bit of that punch we’re more used to, “My Boo” showed an alternate reality. — Andrew Cox


90. Blur – “Girls & Boys” (1994)

Blur’s “Girls and Boys” fascinates me, because I don’t think this song is as simple as some assume. While still being an absolute jam, “Girls and Boys” speaks to the culture around sex in the early 90’s. The iconic chorus — “Girls who want boys/ Who like boys to be girls/ Who do boys like they’re girls/ Who do girls like they’re boys” — celebrates the loosening of gender roles and seems to strip the shame in that lifestyle. But there’s an underbelly too, with Albarn in the first verse singing, “Love in the 90s is paranoid,” alluding to the continuing AIDS crisis. — Cheyenne Bilderback


89. The Smashing Pumpkins – “Cherub Rock” (1993)

“Cherub Rock” was the lead single for Siamese Dream, but it was in spite of the record executives at Virgin who preferred “Today.” The irony comes into play when you consider the song’s lyrics about the commercialization of indie music with the Smashing Pumpkins at Virgin records being front and center. He sings “Let me out” even as this was his entry point to being a household name. “Cherub Rock” stands apart from the Smashing Pumpkins’ other commercial material as a Rush/prog metal-indebted venture with some of the most rollicking guitar/drum interplay of the decade. — Andrew Cox


88. Mariah Carey – “Always Be My Baby” (1995)

I thought I knew everything about my best friend; I was wrong. It was the fall of 2018 when I found out that she was one of the biggest Mariah Carey fanatics. She managed to hide it until one day I played a cover of “Always Be My Baby” that I was obsessed with at the time. As I began to attempt one of the 20 runs in this song, my best friend projected out each note with such ease. I stopped, turned, and asked, “WHAT.” With a shrug she explained that she went through a big phase in middle school, owning every album from her self-titled debut to the more recent Me. I Am Mariah… The Elusive Chanteuse. Mariah entered her second key as my mouth sat open. I let the harmonies, hallmark 90’s beat, and overwhelming sentiments flood me. Maybe I don’t know everything. I shrugged back at my friend: I do know that I love this song and my best friend. — Sadie Burrows


87. Eminem – “My Name Is” (1999)

Eminem would be the biggest artist of the first half of the aughts with album sales rap music had never seen or will ever again. But first, this. His Slim Shady persona was his mainstream voice with the “whiteness” turned up to 11 and humor masking his problematic lyrics with a wink and grin. He would basically make “My Name Is” two more times with “The Real Slim Shady” and “Without Me” — I often get the lyrics of the three songs mixed up. The presence of Slim Shady meant you were getting an instantly-quotable, amateurish delight. We could mock the flimsy nature of pop culture alongside him, even as he eventually became bigger — and messier — than everyone he name-checked. — Andrew Cox


86. Luniz (ft. Michael Marshall) – “I Got 5 on It” (1995)

I had a reaction the first time I listened to “I Got 5 on It” that I wonder if anybody else had: this has to be a remix — no way a beat sounded like this in ’95. That reaction might have to do with its constant sampling and freestyle use by artists like Meek Mill and Yo Gotti. Apart from Michael Marshall’s ’90s R&B hook, “I Got 5 on It” might be the most ‘2020’ song on this list. That ‘2020’ vibe extends to the song’s lyrics about pulling together money to buy weed. I heard it recently on a Krystal’s commercial for some $5 special. It’s a nice fit; you know there’s a lot of weed involved in the making (and purchasing) of those burgers. — Andrew Cox


85. Bell Biv DeVoe – “Poison” (1990)

We’re talking 90s, so you’re going to be hard-pressed to find a better dance track than Bell Biv DeVoe’s Poison. The soft voices complaining about how terrible some harpie is over a New Jack Swing-type beat is never going to get old.

The track is heavily interpolated in today’s Hip Hop landscape, but I’m surprised it’s not sampled more. The bassline, the drums, the synth-like whines are amazing, yet it’s this call out that the culture needs right now.

For better or worse, folks online are picking at inauthentic women. Whether their plastic bodies are promoting dangerous fitness regimens or their plumb booties are selling mass-produced clubwear, matters not.

My proposition is this, call out culture, stans with too much time and internet trolls should reinvent themselves in this plight against unattainable women with “Poison” as their anthem- ha! — Chanell Noise

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84. PJ Harvey – “Rid of Me” (1993)

For nearly half of it, “Rid of Me” is the quietest rock classic this side of “I’m on Fire.” Harvey’s lying in the weeds and letting everyone know she’ll refuse to be alone — unless it’s by her own doing (“I’m going to twist your head off, see”). Then she explodes, skating the line between wanting to be cast aside and knowing it’s inevitable since she can’t control the narrative of the relationship. In PJ Harvey’s deep catalog, Rid of Me and its title track remains her best with her natural talent, innovation, and passion all coming together at once. — Andrew Cox


83. Dr. Dre (ft. Snoop Dogg) – “Deep Cover” (1992)

“Nuthin’ But a ‘G’ Thang” takes most of the glory as the introduction of the greatest West Coast tag team to do it, but “Deep Cover” came first. The soundtrack hit was Dre’s first single, and the first appearance of Snoop Dogg on record; they were ready from the jump. It’s in contention for Dre’s best beat with the “I can feel it” sample from The Undisputed Truth’s “(I Know) I’m Losing You” kicking it off (this is the same one used extensively on Kanye’s “Fade”). I could listen to Snoop saying, “Cuz it’s 1-8-7 on the undercover cop” all day. Now put it on Spotify — come on. — Andrew Cox


82. New Radicals – “You Get What You Give” (1998)

This one’s for the kids and the dreamers, man. The earnest passion on the New Radicals’ only major hit can at times be wrongly dismissed as hippie privilege. Sappy lines like “This whole damn world could fall apart / You’ll be okay — follow your heart” don’t necessarily help, but I’d argue this mix of optimism and piss-and-vinegar attitude balance out with the ’90s alternative dejected vibes. New Radicals understood the world is shit and it perpetually takes aim at the youth — we don’t have the money, the safety nets to invest in our creative dreams, or even vote for the president we want. They came as fast as they went, dissolving in ’99. Also, New Radicals raided a mall for the music video before Avril Lavigne made it cool. — Andrew Cox


81. Blackstreet (ft. Dr. Dre & Queen Pen) – “No Diggity” (1996)

Even though I was born in 1996, the year “No Diggity” was released, I still remember listening to and experiencing this song at various times growing up. It’s also a song that piqued my interests into seeking out more ’90s hip-hop/R&B. Between Blackstreet’s crooning and Dr. Dre’s and Queen Pen’s verses, “No Diggity” blends mellow and aggressive moods together. It feels bouncy and minimal, yet still so sexy. Blackstreet’s most lasting hit — and only — stands as a foundational classic of the R&B/hip-hop genre mash-up. — Cheyenne Bilderback

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80. Built to Spill – “Carry the Zero” (1999)

From my first listen, I was immediately entranced by “Carry the Zero.” I’m not sure if it was Doug Martsch’s warm, comforting vocals, or the freedom I could feel within the guitar riffs, but the combination of that and more made me want to listen over and over again. There’s a strong sense of familiarity within the lyrics, too, as Martsch sings, “I was trying to help, but I guess I pushed too hard.” I first heard it in the summer of 2017, the addictive bridge carrying me home as I drove back from my senior year of college. The rush of layered guitars and clashing drums is both invigorating and cathartic, with Built to Spill creating a special kind of emotional release. — Virginia Croft


79. Guns N’ Roses – “November Rain” (1991)

Known largely for their hard-hitting classics like “Sweet Child O’ Mine” and “Welcome To The Jungle,” Guns N’ Roses showed they can easily slow things down with their Use Your Illusion hit “November Rain.” Though it may be a bit jarring to hear the rock legends playing a ballad complete with lush, sweeping strings and somber woodwinds, staple elements of the band like tight rhythms, precise guitar lines and Axl Rose’s passionate vocals give it a signature edge. The real treat, however, is in the final 2 minutes, where the song goes into its gloriously theatrical finale featuring an iconic guitar solo by the one and only Slash, turning a typical hard rock ballad into something truly special. — Drew Pearce


78. Yo La Tengo – “Autumn Sweater” (1997)

The moment I hear the lone drum beat that introduces “Autumn Sweater,” I smile. It’s a song you can both move and bum out to; the lyrics are equal parts melancholic and romantic; it features an enticingly textured musical arrangement that can be jammed on—in short, it contains all that has made Ira, Georgia and James legends of underground rock. The plaintive anxiety in Kaplan’s voice—“Is it too late to call this off?”, “We could slip away/Wouldn’t that be better”—suits perfectly the queries at the song’s core. That desire to turn your back on the world and disappear with someone or something you love is what records and music and art and books and love are all about: creating a private world for ourselves, one more beautiful than the one we were forced into at birth, if only for a little while. An impermanent but essential comfort, a respite not unlike a favorite autumn sweater. — Donovan Farley


77. A Tribe Called Quest – “Can I Kick It?” (1990)

Yes, you can! The call and response responsible for presidential reference and preference, the Native Tongues golden-era of conscious rap, the abstract track heritage and brotherhood birthing the bang of “before this, did you really know what live was?”—living, breathing; I cannot write anything truer than has already been said about A Tribe Called Quest, Can I Kick It? by Idris Goodwin, breakbeat poet: “made English a dance floor I could go on and on and on ’til break” or how “black folks have been creating with their backs against the wall for years, telling the future” says Hanif Willis-Abdurraqib—the song, the first perfect 5-mic from The Source, that bass line Lou Reed got all the money for, kicking the word ‘it’ around, cannot keep still, freedom is physical: “rock and roll to the beat of the funk fuzz / Wipe your feet really good on the rhythm rug” like the doormat when you get home, rest in rhythm Phife “is a poem sayer” or a much younger Q-Tip than I met in the White House, People’s Instinctive Travels and the Paths of Rhythm plays in our van while we are lost and stuck on the road and not wanting to come home, can we kick it, the virus? Ali’s beat? sample the history, prophetic hymns, Dinkins became the only black mayor of NYC, playful rhymes, while Tribe’s “funky behavior” break-up broke our hearts and had fun with it, while forever on the flying turntable, rap act gone down in measure, offering a hug or “breath of fresh air”, asking 

what makes us move

or snap our fingers

bob our head


— Lagnajita Mukhopadhyay


76. Beck – “Devils Haircut” (1996)

1996 was only three scant years after Beck fell into the position of Generation X’s slacker spokesman, and it turned out what more he had to say was embedded in layers of sampled noise. “Loser” had become a sleeper hit and rather than flip the script for Odelay, Beck and the Dust Brothers chose to dig into their heels. “Devils Haircut” offered more: more breakbeats, more lyrical befuddlement, more minuscule samples giving way towards an idiosyncratic cacophony of music, genre be damned. Beck refused to give it to us straight, peppering his deadpan raps with references to garbageman trees, rotten oases and dropout buses. This was no “Walk This Way.” What “Devils’ Haircut” happened to be was a paranoid witch brew of convoluted surrealist fare. “Rock ‘n’ roll, know what I’m saying,” Beck offers up in that laconic drawl. You can almost picture the sneer on Beck’s face before the drums come back in to tear everything apart – again. — Jibril Yassin


75. TLC – “Waterfalls” (1994)

What’s so interesting about TLC’s 1995 hit “Waterfalls” is its use of contrast. The track has a smooth, slinky production complete with sunny horns and an easy bass line. Hidden in the song’s funky instrumentation are references to heavy issues of the ‘90s like the HIV/AIDS epidemic and the dangers of street violence. How does a song with such heavy lyrical content feel so light? In addition to the overall laid back groove of “Waterfalls,” the track has a singable, almost anthemic chorus, which not only keeps it from being too preachy, but also more radio friendly and bright. With all this in mind, it’s no surprise how huge the song was, spending seven weeks at No. 1. — Drew Pearce


74. My Bloody Valentine – “Soon” (1990)

For a brief glorious window, it felt like anything could happen. The late ‘80s were home to a huge leap in technology and convergence in British indie music, where guitars and turntables no longer seemed like an odd pairing. Kids were going to underground raves where DJs would play hours upon hours of acid house and psych-pop. Bands began to respond to this shift, with none as dramatic as My Bloody Valentine, a group that went from Smiths-indebted jangle to something wholly unrecognizable. “Soon” is an ode to the short-lived Second Summer of Love. My Bloody Valentine’s recognizable roar of guitars and unrecognizable vocals stay in the air, buried under drum loops and textures to create a moment that felt unlike anything else in their catalogue, even on their magnum opus Loveless. It makes for a collision of sound that wasn’t recognizable as dance but carried itself with the same propulsive, trance-like feeling and wouldn’t sound out of place in your DJ set circa 1990. — Jibril Yassin

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73. Ghostface Killah (ft. Raekwon & Cappadonna) – “Daytona 500” (1996)

When you listen to Wu-Tang Clan on 36 Chambers, Method Man and Raekwon stand out as the ones who would break out first. Method had the voice and came out first with ’94’s Tical, but he was soon outdone by the other four major members who all had classic albums by ’96. Ghostface’s was last, and Ironman is more of a display of Wu-Tang’s aesthetic rather than being an unhinged masterpiece like Supreme Clientele or Fishscale. That doesn’t mean everyone’s not at their peak, including Ghostface. The song’s halfway over before he blasts in with lines that should not work like “Yo jostling these cats while Little J be deli-ing / Sip Irish moss out of wedelians.” A wedelian is a fucking obscure flower that rhymed with the last line and also kinda sounds like “weed” in it to connect back with Irish moss — he’s on a different plane than us. — Andrew Cox

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72. Nirvana – “Scentless Apprentice” (1993)

I’ll admit this is not a consensus pick for the best song off In Utero, but it best displays where Cobain was going and what else he could’ve made. He had no intention on resting on his laurels and toning it down. He couldn’t do it in life, and it wasn’t going to happen in his music. His larynx sounds dangerously fried as he pushes the most fragile instrument on Earth to its limit. Few had sung this raw; nobody had done it while singing something like “electrolytes smell like semen.” The beauty of it all was that even at his most elusive and barbed, he didn’t know how to not make pop music. We’ll never know how he would’ve kept pushing himself, so I just keep holding onto and replaying “Scentless Apprentice.” — Andrew Cox


71. Ice Cube – “It Was a Good Day” (1992)

“It Was A Good Day” is Ice Cube’s interpretation of a good day — one of seemingly few that Cube has in his discography. The positive vibes worked to make for Cube’s highest-charting single. There’s a smoothness to the song (thanks to the Isley Brothers’ “Footsteps in the Dark” sample) as Ice Cube runs through the events of his good day (Breakfast, Yo MTV Raps!, the Lakers beating the SuperSonics, RIP). But the “good” might be a misnomer when you consider the anxiety littered throughout Cube’s verses, found in lines like “Plus nobody I know got killed in Central L.A.” or “Will I live another 24?” It’s a positive song with a true purpose of letting you know a good day is the outlier. — Cheyenne Bilderback


70. 2Pac (ft. Dr. Dre) – “California Love” (1995)

2Pac was never bigger than when he was released out of prison and newly signed to Death Row Records. Arguably the most skilled rapper at the time with a dynamite personality and a legitimate movie career to boot had linked up with Dr. Dre — a stand-in by this point for all the ritz and mafioso style of West Coast hip-hop. The first single had to go out to Cali. It was originally intended for Dre’s long-awaited second album, but when that never materialized, 2Pac forever claimed the song’s legacy. But that had already happened when he yelled out, “Out on bail fresh out of jail, California dreamin'” and announced his comeback. — Andrew Cox


69. Elliott Smith – “Between the Bars” (1997)

Akin to Bob Dylan’s switch to electric or Miles Davis’ stark transition of sound with Bitches Brew, Elliott Smith’s third studio album, Either/Or, marked the addition of sonic elements beyond an acoustic guitar and Smith’s hauntingly doubled vocal tracks. These changes can be heard through brush-played drums, bass, and even synthesizer lines, but in “Between the Bars,” they are nowhere to be found. This song seems to linger in the back of your head long after it’s over, courtesy of Smith’s barebones recording style of acoustic guitar and closely tracked, haunting, whisper-like vocals. Despite the album’s lack of initial commercial success, Either/Or is often regarded as the greatest record among Smith’s catalog, with “Between the Bars” and a few other songs being featured in the 1997 film Good Will Hunting. — Scott Hale


68. Bone Thugs-N-Harmony – “Tha Crossroads” (1995)

When Bone Thugs-N-Harmony are called the most melodic hip-hop group of all time, “Tha Crossroads” is the reference point. It’s not really rap, but it could only be made by a group of rappers trying to be Jodeci. The song’s in honor of Eazy-E who died of AIDS that same year — a huge loss for a hip-hop world that would need to prepare for more idols to leave in the next few years. The song’s bigger than Eazy though or anybody referenced in the song; it’s about asking why we die and just hoping there’s a place to see everyone again. “Better believe Bone got a shoulder to lean on.” — Andrew Cox


67. OutKast – “Rosa Parks” (1998)

The ESPN documentary The Last Dance has been a nice companion piece to some of the great ’90s rap appearing on this list. The best part of the series is the montages of Michael Jordan absolutely dominating the court soundtracked by a rap classic. One episode focused on one game against Atlanta in ’98, and you can feel the hype when the “Rosa Parks” intro fades in. It’s like no party rap anthem ever made, comically building off a civil rights leader story and featuring a harmonica solo. To cap it all off, Rosa Parks actually sued OutKast for defamation, and it had to be settled outside of court in 2005. Parks didn’t understand it was an honor to be aligned with OutKast in any way. — Andrew Cox


66. Warren G (ft. Nate Dogg) – “Regulate” (1994)

Warren G’s and Nate Dogg’s legacies circle around this smooth rap/R&B classic — one that reached #2 on the Billboard Hot 100 charts. Warren G provides the standard West Coast sound of the time, while Nate Dogg sounds more like Slick Rick from “Children’s Story” fully leaning into the fairy tale vibe of the ’80s classic. The song liberally samples Michael McDonald’s “I Keep Forgettin’ (Every Time You’re Near)” bringing the original’s laid-back funk into the narrative style. When Nate Dogg passed away in 2011, instead of looking at his contributions to The Chronic or solo work, people went back to “Regulate” — the perfect use of his oddball genius. — Andrew Cox


65. The Notorious B.I.G. – “Hypnotize” (1997)

The stars aligned for “Hypnotize.” The song writer for Herb Alpert’s 1979 single “Rise” (Herb’s nephew Randy Alpert) turned down offers to sample the song until Puff Daddy looped it for Biggie. The original’s disco groove turned into a sinister minimalist bass that has become synonymous with the lavish east coast rap sound. The song reached #1 posthumously, but it probably would’ve topped the charts anyway since it entered the charts at #2 behind, you guessed it, a Puff Daddy song. The hook interpolates Slick Rick on the chorus — a sign that someone knows they’re a legend; Jay-Z would do the same to open The Blueprint in ’01. — Andrew Cox

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64. Smog – “Teenage Spaceship” (1999)

Bill Callahan has steadily made great music across three decades, but arguably 1999’s Knock Knock is the place to start. Its best track, “Teenage Spacheship,” is restraint at its most beautiful. Every line from Callahan here is thought-through and given the space to breathe. His delivery never oversells what he has to say, and it does wonders for simple images like “people thought my windows were stars.” The drums don’t truly kick in until the lyrics are almost over. As Callahan’s mystical cult status continues to grow, “Teenage Spaceship” stands as a totem of why we continue to be so drawn to his every word. — Andrew Cox


63. Pete Rock & CL Smooth – “They Reminisce Over You (T.R.O.Y.)” (1992)

“They Reminisce Over You (T.R.O.Y.)” isn’t a party anthem or even all that groundbreaking, but if you want a perfect, technically-sound Golden age hip-hop classic, look no further. That makes it sound boring, but “T.R.O.Y.” gets at the heart of hip-hop like few others. Pete Rock takes an obscure sample from a Tom Scott cover of Jefferson Airplane to build the iconic sax hook, but it had to mean more than a good beat. While making it, Rock recalls crying over the death of his good friend Troy Dixon. CL Smooth offers three of the best storytelling verses from honoring his single mother to analyzing the father figures in his life to finally reminiscing over Troy. The song has been interpolated by too many big artists to list them all here, from Kanye to Nas to Gang Starr. Every tour of hip-hop appreciation passes through “T.R.O.Y.” — Andrew Cox

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62. Wilco – “Via Chicago” (1999)

I was only four years old when Summerteeth was released, and my connection to music was nothing notable or memorable at the time. However, as I began to grapple with life’s inevitable confusion, the album seems like it would have been a valuable tool. Summerteeth shows a turning point in Tweedy’s writing, as he created the haunting murder-ballad “Via Chicago,” deceptively sung in a soothing tone. The song reads like a poem, an honest confession of one’s deepest thoughts and fears, like when Tweedy wrote, “Crumbling ladder tears don’t fall / They shine down your shoulders.” Beginning the track with the jarring line, “I dreamed about killing you again last night,” there’s a partial comfort in Tweedy’s delivery—he is so comfortable with his audience, he can dare to write from a point of view that is far from his own. — Virginia Croft

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61. D’Angelo – “Brown Sugar” (1995)

I have an affinity for strong offerings from title tracks, and I can attribute some of this from D’Angelo’s “Brown Sugar.” I love a good album opener, and I love when the title track earns the right to claim the title, and “Brown Sugar” has forever warped my standards. Before ?uestlove was forced to reimagine his approach to drumming on 2000’s Voodoo, D’Angelo had Ali Shaheed Muhammad by his side to provide the boom bap feel which eventually became an entire genre of music itself. The first single from his 1995 album of the same title provided major visibility to the sounds of the neo soul genre being born out of the early ’90s from the work of artists like Eykah Badu, Maxwell, and Lauryn Hill. This is one of the classic weed smoking anthems of the ’90s, but the lyrics are often taken literally, with brown sugar representing the love of a woman. Next time the clock strikes 4:20, put down the Cypress Hill and consider some brown sugar. — Scott Hale


60. The Flaming Lips – “Race for the Prize” (1999)

The Flaming Lips have fallen off through over-saturation. Making vinyl with blood in it, working with Miley Cyrus on some truly horrendous music, and an album every 2-4 years for four decades now. It’s a lot to take in, so just hone in on The Soft Bulletin — the greatest psych-pop album of the ’90s. On the classic, sonic exploration meets emotional burden with a gusto that few have dared before or since. The album opener takes on a story of scientists challenging each other for a cure to save the world. Coyne details their lives and purpose with a simple universal pathos — “They’re just humans.” And right as you’re feeling the weight of the world, the drums kick back in. — Andrew Cox


59. Beastie Boys – “Sabotage” (1994)

Musical chaos. That is the best way to describe this song. With thrashing guitars, whirring record scratches and vocalist Ad-Rock’s angry scream-rapping, the Beastie Boys’ “Sabotage” is an interesting piece of genre bending between rock and hip hop filled to the brim with anger, frustration and anti-authority attitude. When I first heard the mayhem-infused track, I was about ten years old and had no idea what to make of it. It confused me. Listening to it now, I realize that maybe that’s the point. Anger and frustration is hard to understand in the moment. Sometimes it just needs to be let out, and the Beastie Boys did just that on “Sabotage,” allowing them to encapsulate the feeling of rage just dying to be set free. — Drew Pearce


58. Erykah Badu – “On & On” (1996)

An interesting question that I don’t see artists get asked enough is what they imbibed when making their projects? For example, what was Erykah Badu smoking when she made On & On?

I don’t mean to make an unfair assessment of Badu’s creative faculties or process- by no means. She possesses vision very few can hope to muster at their peak and execution that solidifies her in music history. All that said- On & On vibrates well in cannabis-friendly circles.

“Oh my, my, my- I’m feeling high.” sings Badu. What was she smoking? And where can the general public tap in? My guess is plenty of people would want to dip into the tools of the gods for their own projects. — Chanell Noise


57. Nirvana – “Come As You Are” (1991)

There’s something so captivating about the watery, distorted tone of Kurt Cobain’s lone guitar riff in the beginning of Nirvana’s “Come As You Are.” Its dark timbre draws you in, preparing you for a driving beat, raw vocals and catchy melody to join in. Lyrically, the song acts as a call-out to the double standards in the world, with lines like “come as you are, as you were / as I want you to be,” along with “take your time, hurry up / choice is yours, don’t be late.” Cobain spends the chorus reassuring listeners, telling them “no, I don’t have a gun,” which following his tragic suicide can bring a chilling edge to what was originally just a solid grunge song with commercial appeal. — Drew Pearce


56. Deee-Lite – “Groove Is in the Heart” (1990)

Deee-Lite’s lone hit is just one of those odd ’90s concoctions that couldn’t happen in any other time and be as popular, but more importantly, it’s a perfect, everlasting one. The trio behind it came from Ohio, Japan, and Ukraine, and they all came together in the great melting pot of NYC nightclubs. The P-Funk vibe oozes from it in every goofy tonal change and more explicitly with Bootsy Collins faintly ad-libbing in the background. Q-Tip provides a verse, but it’s hard to follow what he’s saying when the beat change hits that hard; they knew to replay it before the last chorus. The classic green-screen music video emphasizes its pure goofy revelry with the acceptance of any style, color, or sex. — Andrew Cox


55. George Michael – “Freedom ’90” (1990)

George Michael’s debut Faith was the best-selling album in the US in 1988; it was bigger than Bad, Hysteria, and even the Dirty Dancing soundtrack. By the ’90s, he was already done with being a pop star. Listen Without Prejudice, Vol. 1 — a Vol. 2 never happened — saw Michael refusing to do traditional promotion and not being the focus of his music videos. The album and its two biggest singles — “Praying for Time” and this — were still a massive success and would cap off Michael’s mainstream peak. “Freedom ’90” was as ambitious as “I Want Your Sex” and as catchy as “Faith,” making it the perfect representation of what made Michael so special and why his recent passing was greatly mourned. — Andrew Cox


54. Aaliyah – “One in a Million” (1996)

It is impossible in the modern day to talk about Aaliyah without talking about R. Kelly. Her short life appeared to have been tainted by her illicit and underage marriage, leaving producers and record executives alike to reject her after the release of her debut album through Kelly’s Jive Records. Though the music world made it difficult for her to escape that shadow, she did exactly that, with One in a Million, after being signed by Atlantic. Departing from the guise of “mentorship” by Kelly, it is undisputed that she grew up all by herself, albeit with some help from the up-and-coming Timbaland and Missy Elliot. At only 17, Aaliyah sounded more confident than ever before, becoming the “Princess,” as she was known, of R&B. The staccato and off-kilter Timbo beat—surprisingly hard—alongside Missy’s soft love lyrics, was different but comforting. Despite the team’s efforts to create a futuristic vibe, the wonder of music leaves us in the modern day craving that old-school sound. The song may not have ever made it past the one in a million status, but the trio, the presence of Aaliyah, and the legacy she left behind, definitely did. — Lagnajita Mukhopadhyay

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53. Bikini Kill – “Rebel Girl” (1993)

The first time I heard a female singer doing anything close to screaming was this song. I grew up in the #1 most conservative city in America — Mesa, Arizona, a Phoenix suburb known for its sprawling retirement communities and not much else. I spent my summers tramping around my desert neighborhood and met my fair share of cool, older girls, who seemed to know exactly what to wear, how to style their hair, and which abandoned drainage tunnels were best to explore. In “Rebel Girl,” my childhood becomes something important — revolutionary, even. To be a girl admiring other girls, making friendships with other girls, is radical, cool, and worth screaming about. I only wish I’d heard this song earlier. — Heather Jensen


52. The Pharcyde – “Passin’ Me By” (1992)

Amongst the harsh and unforgiving gangsta rap scene of Los Angeles in the early 90’s, these new kids rolled through the neighborhood laughing like New York would have been if it was always summer—they were The Pharcyde. A younger, less serious, more politically reckless A Tribe Called Quest, they were bringing character and jazz to an otherwise bleak world of violence. Off of La Cienega Boulevard, these hooligans—Bootie Brown, SlimKid3, Imani, and Fatlip—were hollering at girls and writing rhymes, all “sunshine and soda pop,” unbothered by the industry’s expectations of being ‘hard.’ Slim could joke and say that he “was one of those neutral cats because…well, first of all, I couldn’t fight,” but as Fatlip explained, for them, “each line had to mean something.” Their greatest song, “Passin’ Me By,” off of their debut album Bizarre Ride II The Pharcyde, was everything that you didn’t know you needed: Quincy Jones’ “Summer in the City” meets shroom-fueled Jim Morrison impression meets J-Swift’s multi-layered sampling genius paving the way for future beat-making. The classic sing-songy tale of unrequited love, leading to the realization—“I guess a twinkle in her eye is just a twinkle in her eye”—could have made this rag-tag quartet big, if they were more interested in fame. From the start to Fatlip’s legendary climax verse, the song was refreshingly authentic for its time, uncaring and sonically cool. Quickly becoming their only long-lasting anthem, it reminds us of a golden time when, as Slim admits, “Everything was music. Everything was entertainment for us.” — Lagnajita Mukhopadhyay


51. U2 – “One” (1991)

I spent a sizable portion of my childhood listening to U2 in the backseat of my dad’s midlife crisis convertible, whipping around roundabouts and speeding through intersections. This particular song, the slow croon of Is it getting better / or do you feel the same? accompanied the flicker of yellow streetlights, the constellations that I was slowly learning, the sensation of growing up. The song navigates slowly, huskily through a handful of Biblical references and allusions to conflict, before advocating for unity. Though I didn’t care about or understand the lyrics when I was little, listening to Bono pleading for unity, accompanied by the same nostalgic chords in the background, brings me comfort even now. — Heather Jensen