1999 — it’s been twenty years since the dawn of Y2K. I’ve seen other sites rank a bunch of songs from this year, but all of them included “Smooth,” so I’m doing my own. To count as a 1999 song, it had to be first released in this year. Songs from 1998 albums that were released as singles in 1999 are not included, and neither are songs from 1999 albums that were singles in 1998. My goal here is to present a list of the best songs from the most important/influential artists of the era — that’s all subjective, so whatever. Enjoy!


100. Leila – “Sodastream”

Leila’s first single for her second album is a complex lo-fi bop. With ties to Aphex Twin and Björk, she is an essential act in the late-’90s/early-’00s.


99. Foo Fighters – “Learn to Fly”

Foo Fighters are bound for one-to-two essential jams every album, and “Learn to Fly” off There Is Nothing Left to Lose is one of their best.


98. Matmos – “Last Delicious Cigarette”

The West preceded Matmos’ crowning achievement 2001’s A Chance to Cut Is a Chance to Cure and featured much of the experimental IDM bliss to come. The epic, winding opener “Last Delicious Cigarette” is one of their best.


97. Supergrass – “Pumping on Your Stereo”

Supergrass’ lead single for Supergrass is the best unreleased Sticky Fingers/Ziggy Stardust cut of 1999.


96. Azzido Da Bass – “Dooms Night”

“Dooms Night” would take a few remixes to finally take off as a top-10 UK hit, but what made this vogue-esque lurch succeed is still all there in the original German release in 1999.


95. Paul Johnson – “Get Get Down”

“Get Get Down” borders on obnoxious simplicity, but it has enough of that classic Chicago house bounce to make it worthy of its status as a worldwide hit.


94. Looper – “Impossible Things #2”

Looper was a Belle & Sebastian offshoot that had more in common with the palatial, electro-acoustic sounds of Air and Stereolab. Stuart David’s soft musings and a harmonica carry you through the first proper song on their debut.


93. Plaid (ft. Benet Walsh) – “Ralobe”

Plaid are hard to pin down as they cast a wide net of electronic trends with each album. On “Ralobe,” Plaid lean into Benet Walsh’s beautiful guitar work for a luxurious yacht rock ambience.


92. Tindersticks – “Can We Start Again?”

Stuart A. Staples had one of the greatest baritone voices of the ’90s — up there with Berman and Callahan. With a voice like that, the band had to just keep it short and simple to make something great.


91. The Clientele – “An Hour Before the Light”

The Clientele spent the late-’90s releasing great singles and EPs that would culminate into the classic Suburban Light. “An Hour Before the Light” doesn’t break from or challenge what they were doing at the time, so it’s obviously great.


90. Rage Against the Machine – “Guerrilla Radio”

Rage Against the Machine’s aggressive politics have aged beautifully, unfortunately. Since their demise shortly after 1999’s The Battle of Los Angeles, RATM’s anger hasn’t properly been replicated.


89. The Chemical Brothers (ft. Noel Gallagher) – “Let Forever Be”

Gallagher’s first collaboration with The Chemical Brothers, “Setting Sun,” is an undeniable classic, but “Let Forever Be” is actually the more popular of the two (according to Spotify). More importantly, it’s also really good.


88. The Auteurs – “The Rubettes”

The Auteurs ask “Weren’t the nineties great?” on their last single before disbanding. The line follows a nostalgic look at the communal love of rock & roll through jukeboxes and Sunday morning countdown shows. Among swan songs, this one’s up there.


87. Stereo Total – “Joe le Taxi”

On this album closer, Stereo Total capture a middle ground between Serge Gainsbourg and Suicide for a stunning slice of French electro-pop.


86. Boredoms – “◯”

Vision Creation Newsun is an album that shouldn’t be taken piece by piece, but if you want a good sense of what this album has in store, look no further than the 13+ minute opener.


85. Mouse on Mars – “Distroia”

Every Mouse on Mars album is an essential listen, and “Distroia” is one of their most accessible tracks with their usual experimentation matched by an high energy rhythm.


84. Tom Waits – “Big in Japan”

Waits’ genre fluidity and gravelly voice aged gracefully in equal measure in the ’90s, and “Big in Japan” is just classic Waits packing so much characterization into every lyric with ever-shifting accents and tones.


83. Alex Gopher – “The Child”

House music in the late ’90s/early ’00s catered to classic French romanticism with its icy, cool sexiness, and French DJs like Alex Gopher fit the bill to soundtrack the clubs and movies of the time like Amélie.


82. Q-Tip – “Vivrant Thing”

The production collaboration of Q-Tip and Jay Dee created this undeniable, hard-hitting beat, so all it needed was Q-Tip’s reliably smooth verses.


81. Ginuwine – “So Anxious”

It isn’t “Pony,” but “So Anxious” is a classic R&B sex jam, nonetheless. Timbaland’s production here is tamed down and patient to set the mood.


80. …And You Will Know Us by the Trail of Dead – “Mistakes and Regrets”

Trail of Dead were on the verge of a breakthrough, but arguably, “Mistakes and Regrets” is their best song being the slowcore battle cry they excelled at.

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79. Prince Paul (ft. De La Soul) – “More Than U Know”

Prince Among Thieves isn’t a normal album with skits carrying the album just as much as the actual songs. Of course, the most popular song here is the one featuring De La Soul, who Prince Paul produced up to ’94.


78. Jim O’Rourke – “Eureka”

Every Drag City release from Jim O’Rourke in the late-’90s was magical, and the nine-minute title track for Eureka might be the best slice of his delicate folk pop.


77. Donell Jones (ft. Lisa “Left Eye” Lopes) – “U Know What’s Up (Remix)”

Donell Jones’ second album Where I Wanna Be was his peak, critically and commercially, and the big hit “U Know What’s Up” was emboldened by a remix from TLC’s “Left Eye” post-“No Scrubs.”


76. Blackalicious – “Deception”

’99 was the peak of Sisqo, but (spoiler alert) “Thong Song” isn’t making this list. Instead, here is Blackalicious’ “Deception,” which is a complete takedown of his soul-selling success and impending fall from grace.


75. Smog – “Cold Blooded Old Times”

“Cold Blooded Old Times” undercuts the baby boomer nostalgia for old times with a tale of marital abuse and consequently, the aftermath of a patriarchal family structure in dismay. It was also on the High Fidelity soundtrack.


74. Basement Jaxx – “Rendez-Vu”

Remedy was the first of two classics from Basement Jaxx and kicks off with “Rendez-Vu” – a somewhat subdued version of their candy-colored aesthetic.


73. Blur – “No Distance Left to Run”

If 1997’s Blur wasn’t a comedown from the highs of Britpop, then 13 made it very clear. Nowhere is this more clear than on “No Distance Left to Run” — one of the most desolate, heartbreaking hit singles ever released.


72. Nine Inch Nails – “We’re in This Together”

Everything about Nine Inch Nails’ last great album is overblown into epic proportions, and if you want to go epic, you allude to Bowie’s “Heroes” such as Reznor does here.


71. Aimee Mann – “Save Me”

“The song that lost an Oscar to Phil Collins and his cartoon monkey love song” — Aimee Mann (Austin City Limits Music Festival 2006). Like everything involving Paul Thomas Anderson, Aimee Mann’s work on Magnolia is simply majestic.


70. Dismemberment Plan – “What Do You Want Me to Say?”

Dismemberment Plan peaked at the height of emo and have relatively none of the audience that a group like, say, blink-182 have (spoiler again — not on this list). “What Do You Want Me to Say?” is definitely the best sing-along anthem on their classic Emergency & I.


69. Fatman Scoop (ft. The Crooklyn Clan) – “Be Faithful”

A #1 hit in the UK and Ireland, “Be Faithful” is certainly one of the most sample-heavy worldwide hits. Looking back, Fatman Scoop is seen more as a novelty act, but his success displayed the pervasive role of plunderphonics in the music industry.


68. Madonna – “Beautiful Stranger”

Madonna used the, um, Austin Powers sequel soundtrack to further explore the luxurious production style she adopted on Ray of Light. It was her last foray in this style before doing whatever Music was in 2000.


67. The Aztec Mystic (a.k.a. DJ Rolando) – “Jaguar (Knights of the Jaguar)”

Just through the power of this one track, DJ Rolando has been a prominent name in the rich history of Detroit techno. The great momentum and texture of the original mix explains why.


66. Mos Def – “UMI Says”

Mos Def, now Yasiin Bey, presents his clearest mission statement on “UMI Says”. He wants to live in his peace with all Black people free. That the message of hope in the chorus comes from his family speaks to the communal desire for freedom.


65. Sigur Rós – “Starálfur”

Almost halfway in “Starálfur,” all that is audible is a scratchy acoustic guitar. It is a jarring moment in an album defined by its pristine elegance. What immediately follows is that wonderful keyboard line with fireworks popping all around — stunning like most else on their breakthrough album.


64. Moby – “Porcelain”

Play is not the classic many believe it is. In many ways, Moby just capitalized on being a prominent name making an “it” sound — that cool house music I mentioned before with #83. “Porcelain,” recently sampled by A$AP Rocky, is probably the best track on it due to Moby just letting the mood ride.


63. Sasha – “Xpander”

By ’99, Sasha (Alexander Paul Cole) was remixing Madonna, soundtracking Playstation games like Wipeout 3, and releasing one of the most legendary trance tracks ever in “Xpander.” At over 11 minutes, “Xpander” commands a room through sheer blunt force and mesmerizing circular rhythms.


62. Cassius – “La Mouche (DJ Falcon Metal Mix)”

Philippe Zdar recently passed away and what he left behind was some of the best French house music of the mid-to-late nineties. His work with Boombass as Cassius has stood the test of time, and this remix of one of their singles is a stratospheric delight.


61. Mary J. Blige (ft. Lauryn Hill) – “All That I Can Say”

This song doubles as a great cap-off to Mary J. Blige’s legendary nineties run and the last time we truly saw Lauryn Hill at her peak. The song was written and produced by Hill and could have easily fit on Miseducation.


60. Armand van Helden (ft. Duane Harden) – “You Don’t Know Me”

“You Don’t Know Me” was the culmination of a busy nineties for Helden remixing Tori Amos and Sneaker Pimps, which brought speed garage to the forefront of popular electro at the time. “You Don’t Know Me” was his original composition and became a #1 UK hit (notice a trend here with the UK and electro in ’99?)


59. The Roots (ft. DJ Jazzy Jeff & Jazzyfatnastees) – “The Next Movement”

Alternative hip-hop had one of its greatest years in ’99, and The Roots were leading the way with Things Fall Apart. “The Next Movement” is one of the most dynamic songs on the album with great energy, an accessible hook, and a scratching outro.


58. DJ Zinc – “138 Trek”

“138 Trek” would finally achieve chart success in 2000 as one of the first drum and bass producers to do so. It’s one of the best examples from the time of almost breaking electro music down to just pure electrifying drums.


57. Pavement – “Spit on a Stranger”

Pavement opened their last album with one of the purest pieces of pop rock Malkmus could ever be involved with. The complacency baring down on the band produced at least a few great little mellow ditties on Terror Twilight.


56. The Magnetic Fields – “All My Little Words”

There are roughly 69 candidates off of 69 Love Songs to be on this list. “All My Little Words” stands out as the best lead vocal contribution from LD Beghtol on the album and the lovely interplay and complexity of Merritt’s broad use of stringed instrumentation all over the album (I don’t play any of them, so I’m not going to begin to parse out which ones he uses here.)


55. D’Angelo (ft. Redman & Method Man) – “Left and Right”

Voodoo was imminent; D’Angelo would release “Untitled (How Does It Feel)” on January 1, 2000. Before that though, he gave us “Left and Right” with arguably overbearing verses from Redman and Method Man. D’Angelo almost feels like an afterthought here, but that’s the intention with him blurring into the scenery and vibe all over Voodoo. This single was a bit of a tease, but also a strong glimpse into what mastery was about to drop at the turn of the century.


54. Super Collider – “Darn — Cold Way O’ Lovin”

Head On is a mostly-forgotten classic that is inspired by the funk of Sly Stone as much as Autechre. This is their most popular song, and it hasn’t reached 20,000 stream on Spotify. What a shame. Jamie Lidell would go on to make a name for himself with Multiply, but his Super Collider with Christian Vogel is absolutely essential — a potential path of combining funk and IDM that was never properly explored.


53. Drexciya – “Andreaen Sand Dunes”

Drexciya’s — and The Other People Place’s, of course — drum machines just hit different. Everything about the treble of “Andreaen Sand Dunes” screams drifty and ambient, but the bottom is held up by the quickest little pitter-patter that just gives the song an electric momentum — like a crab holding up the whole coral reef you see depicted on the cover.


52. Eve – “Gotta Man”

The Eve people go to first is the 2001 Scorpion version where she duets with Gwen Stefani for a massive hit. ’99 Eve was still finding her footing in a post-Missy world, but she was in her zone here as a 20-year-old Ruff Ryder describing crime-laced romantic innocence.


51. The Artful Dodger (ft. Craig David) – “Re-Rewind (The Crowd Say Bo-Selecta)”

This duo was a huge name in UK garage who would get name-checked on Original Pirate Material a few years later. They stumbled onto Craig David before he had major success and made this classic, a jolting piece of UK garage pop that could only be made during this era.


50. Pharoahe Monch – “Simon Says”

Those four brass section bursts of impending doom — they signaled Pharoahe Monch’s peak and impending hiatus. The uncleared sample came from Akira Ifukube’s Gojira scores would get him sued and affected his debut album’s distribution. In the crowded Queens rap scene, Monch’s obtuse styles stood out.


49. Destiny’s Child – “Jumpin’, Jumpin'”

Pop doesn’t get more energetic than this; it’s literally in the title. Just listen to the instrumental, and you see the workings of a rave anthem and hip-hop beat simultaneously. Destiny’s Child decided to match that energy down to the syllable, and they pulled it off because in ’99, they just didn’t know how not to.


48. Basement Jaxx (ft. Slarta John) – “Jump ‘N Shout”

I don’t know any of the words to this song other than “dance floor” and “Jump ‘N Shout,” and that’s all that needs to be understood. This is all MC Slarta John is known for and what a way to make a name for yourself.


47. Dr. Dre (ft. Snoop Dogg) – “The Next Episode”

2001 is the dumbest title possible for a ’99 album, and the story behind it is even dumber (it involves Suge Knight so unnecessary drama is a given); it was bound to have two of the most memed songs ever. The uncredited Nate Dogg here has the most famous line — “Smoke weed everyday.”


46. MF DOOM (ft. Pebbles the Invisible Girl) – “Doomsday”

MF DOOM rapping over Sade is untouchable — especially when he’s rhyming Yeti ghetto slang, nipple metal fang, bang-bang, talking orangutans, gin and tang, and yin and yang.


45. Fiona Apple – “Limp”

In all of her collaborations with Jon Brion, this one features probably his best drum work, and that’s saying something. Throw in Apple’s passionate vocals and judge-jury-and-executioner persona, and it’s an absolute banger.


44. Isolée – “Beau Mot Plage”

Here’s one of the most intricate minimalist house tracks that still manages to never sacrifice accessibility. The song catapulted the German producer into a leader of the electronic scene and onto countless mixes for years to come.


43. Beck – “Debra”

Midnite Vultures is Beck’s most divisive album. It’s not unanimously treated as a classic on par with Odelay and Sea Change, because it’s goofy horniness is often just seen as, well, just that. “Debra” and its tale of sororal infatuation is a litmus test for how serious you need your music to be.


42. Mariah Carey (ft. Jay-Z) – “Heartbreaker”

Mariah Carey is not like Madonna or Janet Jackson, where their commercial success is matched by their critical adoration. So much of Carey’s music stayed in the ’90s, to the point where youngsters like me have to go out of their way to find out what made her such a one-of-a-kind star. “Heartbreaker” might be her best song as it adheres to a necessary approach for dynamic voices; the instrumentation has to have enough bounce to not let the technical prowess of the vocals be a drag (maybe Adele can take note).


41. Godspeed You! Black Emperor – “Moya”

GY!BE’s post-rock is timeless. The reliance here on strings and Górecki’s 1976 third symphony repurposes music that was for the elite savants into an anthem for indie outcasts. But at nearly 11 minutes, this slow burn is certainly not meant for everyone.


40. Primal Scream – “Swastika Eyes (Spectre Mix)”

Primal Scream went all in on this one, and it paid off for one of their best songs. The Spectre mix (Jagz Kooner) is a runaway train of a production feat clearly inspired by their fellow Brits Underworld. You have to go epic with the sound of a song about corrupt governments and police states, or you can be accused of half-stepping.


39. Pete Heller – “Big Love”

Ah, that muffled disco sound popularized as “French Touch.” “Big Love” may be the UK’s best representation of this sound. The song was actually made before Stardust’s “Music Sounds Better With You,” and demos and copies were flying around way before it was officially released (Heller sent an original demo to Frankie Knuckles because, of course). “Big Love” stands out for using just one sample and repeating it incessantly. Modern day “French Touch” classics like DJ Koze’s “Pick Up” and Andrés’ “New for U” have followed this pattern.


38. Wilco – “A Shot in the Arm”

In this song, there’s a “we” and a “you.” With a standard reading of “you,” this song’s pretty judgmental: you were up all night smoking, you’ve changed, etc. Of course, the “you” could be Tweedy or the narrator taking an outside perspective of himself. I find that more exciting and more humanizing. This is certainly Wilco’s best single, but they tend to save the best for the album.


37. Built to Spill – “The Plan”

I stand by  thinking Keep It Like a Secret is the Idaho band’s best album. It’s absolutely perfect — ten of the best alternative indie rock songs of any era. The opener “The Plan” is versatile, winding, and peppy.


36. Annie – “The Greatest Hit”

Annie would finally find her audience in 2004 with Anniemal and her actual greatest hit, probably the most underrated candidate for greatest pop song ever, “Heartbeat.” Annie’s first single “The Greatest Hit” was included on the album and was finally reassessed as the classic it is. Weirdly enough, the song samples Madonna’s debut single “Everybody.” Sometimes, it takes more than the song to break through.


35. The Roots (ft. Erykah Badu & Eve) – “You Got Me”

Erykah Badu’s hook here is one of the best representations of the stale “woman-singing-a-hook-on-a-rap-song” style. It completely carries the song much like Alicia Keys on “Empire State of Mind” but obviously subtler. The drumming on the outro is also a nice touch to give the song some edge as it fades away.


34. Lil Wayne – “Tha Block Is Hot”

One of the greatest runs in hip-hop history starts here with his debut single. Here, Mannie Fresh’s iconic production steals the show as he tended to do around the time (“Ha,” Back That Azz Up,” and “Bling Bling” all belong to him). Lil Wayne sounded different than his Hot Boys team though as his voice didn’t seem able to be confined just to New Orleans.


33. Le Tigre – “Deceptacon”

The definitive version might be the DFA remix, but that was just an extension of Kathleen Hanna’s innate ability to create iconic one-liners all over songs like “Deceptacon.” At barely 3 minutes, all of those great lines pile up at a rapid pace to create one of the most joyous indie rock jams.


32. Pavement – “Major Leagues”

This is Pavement’s last single/EP. They seemed to know the 21st century just wouldn’t be for them, and we may never find out if that’s true. Like the best of Terror Twilight, the melancholy reigns supreme even if the lyrics are something about major leagues and bad girls — who cares? Pavement — much like the stereotypical version of the ’90s — were always about empty coolness, and it’s captured beautifully here.


31. B.G. (ft. Big Tymers & Hot Boys) – “Bling Bling”

B.G. isn’t a well-known name like Juvenile or Lil Wayne, but on ’99’s Chopper City in the Ghetto, it seemed like he was primed to be. With an aesthetic much like Juvenile’s, B.G. got a top-40 hit with “Bling Bling” with an iconic hook from Lil Wayne. It’s the best representation of the New Orleans rap scene outside of Guerrilla Warfare.


30. Blur – “Coffee & TV”

Graham Coxon had just released his first solo album and was prepared to take more ownership of Blur around the time of 13. With “Coffee & TV,” Coxon got his first lead vocals on a Blur single, and it turned out to be their best post-Britpop song. The song’s “normal” style and lyrics both ask for a return to form, for the simple life, or at least just a do-over.


29. Destiny’s Child – “Bills, Bills, Bills”

This is pure pandering; every member of Destiny’s Child could pay their own damn bills and not rely on men to do so. The song’s catchy as hell, though, and you tend to forget about all that by the time they draw out “soooooo” in the hook.


28. Broadcast – “Echo’s Answer”

This is the first single from 2000’s The Noise Made by People just creeping its way into the ’90s. Any song without drums is an odd choice for a first single, but Broadcast thrived on being eccentric. The emphasis is given to Trish Keenan’s lovely deadpan vocals that just glides all the way to its serene conclusion. The song title here is perfect.


27. The Flaming Lips – “Waitin’ for a Superman”

The Flaming Lips’ The Soft Bulletin is the best album from this year, and I don’t think there’s much debate. It’s especially true when you consider how Coyne’s tales of humanity’s inability to prevent the preventable will continue to age clearer and clearer until humanity’s last breath. “Waitin’ for a Superman” may be the most succinct and beautiful way to describe there will be no happy ending we don’t deserve.


26. Dead Prez – “Hip Hop”

Dead Prez were the most militant rap group of their time, maybe ever. More so than anyone, they saw the avenue for hip hop to be a place to teach and change the world, while calling out how hip hop had been corporatized into just another avenue for ineffectual pop music. Here, they trademarked their slogan — “It’s bigger than hip hop (hip…hop…hip…hop).” A lot is packed into that simple rallying call.


25. Bonnie “Prince” Billy – “I See a Darkness”

I See a Darkness and its titular track seem ready to collapse at any moment. The guitars and drums are mixed like they’re constantly fading out. Billy’s frail vocals align him with Elliott Smith and Nick Drake — a notoriously morbid crowd. Everything comes together on the chorus with the proclamation of “And now I see a darkness” — maybe there’s comfort in being able to recognize what’s coming, good or bad.


24. Mos Def – “Ms. Fat Booty”

This was Mos Def’s first single after his Black Star work in ’98, and it still remains his most popular work. The beat produced by Ayatollah samples the early Aretha Franklin single “One Step Ahead.” It’s a classic storytelling rap song with Mos Def laying out the whole aura of this one woman over two verses.


23. Beck – “Mixed Bizness”

It’s not the most notable song off Midnite Vultures — that’s “Debra” and “Sexx Laws” — but there’s a dynamic energy here that best captures the spirit of what Beck was going for. He wanted to see if he could get away with bizarre lyrics by emboldening them through an airtight funk rock style. The brass section shines by fully enveloping the listener in a Parliament-esque atmosphere.


22. Dr. Dre (ft. Snoop Dogg) – “Still D.R.E.”

“Still D.R.E.” was a flop at first. It was the first single for Dr. Dre’s long-awaited sequel to The Chronic featuring Snoop Dogg and one of the greatest piano-led beats ever produced; it peaked at #93 on the Billboard Hot 100. Had the world moved past Dr. Dre? He focused heavily on that subject with the lyrics (penned with/by Jay-Z). Fast-forward to 2019, and it’s one of the most popular songs from this year — only “All Star” and “I Want It That Way” have bigger streaming numbers. Maybe that’s just due to the videos using that piano for comedic effect, but that piano came first and now it’s forever ingrained into our culture as it should have been from the start.


21. Ol’ Dirty Bastard (ft. Kelis) – “Got Your Money”

Who knows where ODB would’ve gone musically if he didn’t pass away in 2004? Based on “Got Your Money,” he was the only Wu-Tang member capable of a crossover hit by willing to work with the up-and-comer Kelis on the hook. ODB’s verses also contributed to it being a hit with his adept melodies and internal rhyme schemes conveying a controlled version of himself. With his loss, the Wu-Tang brand became a straightforward aesthetic that hasn’t been the same.


20. Jim O’Rourke – “Halfway to a Threeway”

Here’s a disturbing song you might just find at first to be a peaceful little ditty. The narrator here is possibly sexually taking advantage of a disabled woman and is looking for one more to complete the threeway. Some people want to read it as an extended metaphor for a loveless relationship or dealing with a split personality, but that’s a convenient loophole to not have to deal with a bizarre, possibly monstrous, narrator. Jim O’Rourke is one of a kind for sure.


19. Fiona Apple – “Paper Bag”

When the Pawn… is one of the most impressive statement albums from an artist gearing up to be ostracized forever. Fiona Apple’s post-“Criminal” ’90s is a bleak display of how ill-equipped the media, tabloids, and music industry are when faced with an opinionated artistic woman. Through all of that, When the Pawn… is an inward, relationship-driven album about what version of yourself that people who care about you will see. The ability to judge Fiona Apple outside of her public persona was all there in her lyrics, especially “Paper Bag” — “I know I’m a mess he don’t wanna clean up / I got to fold ’cause these hands are too shaky to hold.” Better than anyone else at this time, Apple was conveying a complex human drive to conquer your perceived flaws while retaining who you have been from the start.


18. Kelis – “Caught Out There”

This is an ambitious song. That chorus, seemingly filtered as to be said into a phone, is not even sung and has a legitimate whole-body yell you never see in a pop song. The Neptunes production is vibrant, as well. After the last chorus, you hear cascading video-game-like notes lead back into the beat for the outro. You can hear how the early-’00s would shape into the greatest era of pop music since the ’60s all over this track.


17. Christina Aguilera – “Genie in a Bottle”

It’s hard to not hear this without the classic “Hard to Explain” mash-up, but arguably, “Genie in a Bottle” was the better of the two songs in that mash-up. With her comparisons to Backstreet Boys and Britney Spears, you can overlook how weirdly constructed her definitive hit actually is. David Frank worked on this song, and he was responsible for much of the electronic r&b sound of the early ’80s with Chaka Khan and Mtume. Just go back and listen to the first 10 seconds of this song — complete with a buoyant house piano, quick shift into heavy r&b synths, and an unruly drum machine –and tell me how that became a platinum #1 song.


16. Len – “Steal My Sunshine”

This song is up there with “Dancing Queen” and “I Want You Back” for jubilant pop songs that everyone loves in any setting and will never tire of. Fun facts: the song samples the disco classic Andrea True Connection’s “More, More, More,” and on the Steal My Sunshine album, a future member of Broken Social Scene and a past member of Poison were involved.


15. Basement Jaxx (ft. Blu James) – “Red Alert”

Here’s Basement Jaxx’s first of three #1 US Dance hits from Remedy, and it has all their iconic groovy camp. The song liberally samples the bass from Locksmith’s “Far Beyond” and mixes in a lot of background noises to give that club scene vibe. At 2:47, Basement Jaxx throw in a cinematic strings section and layer the rest of the song on top of it to max out the environment that Buxton and Ratcliffe were able to present at their peak.


14. Sleater-Kinney – “Get Up”

“Get Up” is about taking control of your submission to the natural world. That sounds like spiritual nonsense because maybe it is, but we get some clever lines and delivery from Tucker and Brownstein here. My favorite? “Fall down on the world before it falls on you,” or maybe “Are we captive for only a short time?” or just simply “Ooooohh, Watch it go!” Throw in some of Weiss’ best drumming, and it’s a contender for Sleater-Kinney’s best single.


13. Dr. Dre (ft. Eminem) – “Forgot About Dre”

This might be Eminem at his best: ghostwriting possibly Dre’s best verse, providing a killer hook, and then offering possibly his best verse. At his peak, he was untouchable — “And I’m still loco enough to choke you out with a Charleston Chew.” While 2001 captured much of the same Chronic energy with Snoop Dogg, this was the real pass-the-torch moment that signaled a new era for rap music.


12. The Magnetic Fields – “The Book of Love”

Love — what is it and how is it defined? That’s what Merritt examines here, treating is as a book which people analyze and follow step-by-step. He speaks to a universal truth displaying how romance is only decipherable when there’s a face to it, that reality translates what we are told to feel. It’s a simple, impactful classic now consistently covered and popping up in strange places like General Hospital.


11. The Dismemberment Plan – “The City”

Does any track better convey the loneliness people often feel when they’re stuck in a city people have moved beyond? Travis Morrison covers all of this beautifully and succinctly in “The City”‘s first eight lines. The last line goes into full-out melodrama with “All I ever say now is goodbye,” but the more you think about it, it does seem like this world is built for splitting people apart than keeping them together.


10. Sigur Rós – “Svefn-g-englar”

That doppler radar beep is so haunting, meditative, powerful, and uplifting all at once. You can skip to any part of this post-rock epic, and that beep is waiting for you, always where you expect it to be. It’s always nice to revisit where Sigur Rós first made their mark due to how their sound has been made boring by its constant prevalence in soundtracks and five follow-up albums. For me, “Svefn-g-englar” just is Sigur Rós.


9. Smog – “Teenage Spaceship”

This is restraint at its most beautiful. Every line from Bill 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.


8. Eminem – “My Name Is”

“God sent me to piss the world off” — Eminem’s hubris and need to brag about how controversial he was is there from the start, and he earned it. For four years, Eminem was the biggest name in music and selling 30+ million copies of albums with murder fantasies of his wife. What Eminem has been the last few years has normalized him, but there has never been anything like early-Eminem and probably never will be. “My Name Is” was when he could still be written off as a fad — a bug in the machine. The undeniable talent for earworms suggested otherwise.


7. Built to Spill – “Carry the Zero”

“Carry the Zero” is Built to Spill’s best song, which means it’s in contention for the greatest indie rock song ever made. The guitar solo outro is up there with Deerhunter’s “Nothing Ever Happened” and Pulp’s “Sunrise” for best guitar solo of my lifetime. There are a lot of subjective accolades to throw around with a song of this magnitude from a band that reinvented itself across three classic albums in the ’90s.


6. Destiny’s Child – “Say My Name”

That “Say My Name” stands out from one the most loaded pop albums of the ’90s speaks to what rarefied territory this song belongs in. The whole song is the hook with three repeating sections that switch up production styles and rhythms. It is a masterclass in how to construct a pop song that will stand the test of time rather than building around a catchy chorus.


5. Wilco – “Via Chicago”

Summerteeth deals with domestic abuse in its best songs — the last line in “She’s a Jar” is always unsettling. “Via Chicago” starts with “I dreamed about killing you again last night / And it felt alright to me.” Jeff Tweedy explained what that line means to him, and he said, “The feeling of being uncomfortable with what I had written — that felt more real to me than anything I could have constructed.” He also expressed sentiments about letting his bandmates down with this “dismal stuff,” but Summerteeth and “Via Chicago” shine from these thorny scenarios. Art is dead when morality goes unquestioned and our voices adhere to it. “Via Chicago” also reaches instrumental heights that they wouldn’t even pursue on Yankee Hotel Foxtrot.


4. TLC – “No Scrubs”

Where does this chorus rank all-time? They repeat the whole thing eleven times (it fades out on the twelfth) in a three-and-a-half-minute song. Throw in the just-as-catchy pre-chorus twice, and it never lets up. It’s amazing it never gets annoying. It was a #1 hit and the runaway pick for best song in the Pazz & Jop poll (that poll also features “Bawitdaba” just outside of the top ten, so it’s pretty meaningless.) Still, pop songs that unite everyone should always be recognized for what they are — the best of the best.


3. The Flaming Lips – “Race for the Prize”

The sonic ambitions of The Soft Bulletin are unreplicable, and it’s on full display with the opener “Race for the Prize.” Drums just don’t sound this way anywhere else — is it the mic placement? The mixing? Also, that Mellotron string sound is pure psychedelic-Beatles/prog-rock territory, but is used as the main hook on the first single. The Flaming Lips were bold, and they had the means and funding to pull off whatever drug-infused landscapes they envisioned.


2. Jay-Z (ft. UGK) – “Big Pimpin'”

This snuck right into 1999 with a Dec. 28th release. 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.


1. Aphex Twin – “Windowlicker”

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.