To see what else made the list, check out the first part (400-201).

Contributors: Jordan Blum, Nina Braca, Sadie Burrows, Danielle Chelosky, Virginia Croft, Happy Haugen, Brody Kenny, Chanell Noise, Drew Pearce, Leslie Richin. Clay Sauertieg, Alex Wexelman

Graphic Design by Sadie Burrows!


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200. The-Dream – “Rockin’ That Shit” (2008)

The Love Trilogy is the stuff of r&b legend with Terius Nash releasing three legitimate classics in the span of four years. “Yamaha” off the last album is the Prince-indebted all-timer, but “Rockin’ That Shit” is the go-to to get the party started. Not to be confused with his first hit “Shawty Is Da Shit,” The-Dream has really honed in on his sound as a solo artist by his second album. Every line here is catchy with each ad-lib (ayyy, ooooh, ohoooh, etc.) hitting the right note. He even ends a whole verse speechless with “ummm” and it totally works. Nash’s whole brand of r&b had no flaws, and when he wanted a hit, he put every ounce of his talent into it. — Andrew Cox


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199. Beirut – “Postcards from Italy” (2006)

“Postcards from Italy” is like if Sufjan Stevens decided to take his 50 States Project into Europe. It is the most noteworthy track off Beirut’s debut album, Gulag Orkestar, released in 2006. Featuring their signature ukulele strums over a triumphant horn section, the single became one of their most popular tracks. The nostalgia anthem was accompanied by a video featuring home videos of people you never knew but felt like family.  — Nina Braca


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198. Broken Social Scene – “Cause = Time” (2002)

Epochal indie albums came out of the three major Canadian cities in the ’00s with The New Pornographers in Vancouver, Arcade Fire in Montreal, and Broken Social Scene in Toronto. Maybe there’s something to be said about the large collective atmosphere of these acts, but Broken Social Scene captured the tempestuous spirit of indie music more naturally than those two, for better and for worse. This band wasn’t here for straightforward indie pop or anthemic call-to-arms, and that was due to their start as a post-rock instrumental act. The more people they added (eleven officially for You Forgot It in People), the more they behaved like a true rock band. “Cause = Time” is the most propulsive track on the album. — Andrew Cox


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197. Belle and Sebastian – “Your Cover’s Blown” (2004)

After a trio of classic chamber pop albums in the ’90s, Belle & Sebastian didn’t have much to prove for this decade. It showed up a bit in their disjointed releases and stylistic changes throughout much of the ’00s. They released many albums, but the best work popped up in singles and EPs like the geniuinely-weird “Your Cover’s Blown” that behaves like indie pop’s attempt at “Bohemian Rhapsody” or “Happiness Is a Warm Gun.” The bass-heavy, funky six-minute epic is like nothing in Belle & Sebastian’s discography, so it makes a little sense to hide it away on a 4-song EP between albums. Murdoch’s funny side comes through best on lines like “The DJ’s picking up speed / That’s something I just don’t need.” — Andrew Cox


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196. Fiona Apple – “Extraordinary Machine” (2005)

This title track and opener of the idiosyncratic 2005 album demonstrates the type of drama and theatre Apple can fit into a single song. It takes on a life of its own, moving sluggishly along with her voice as she tells something of a mythological tale about her own evolution: “Be kind to me, or treat me mean / I’ll make the most of it, I’m an extraordinary machine.” Other characters come and go throughout, but she makes herself the centerpiece, dismantling misunderstandings and confessing to potential flaws. It’s an intimate introduction into a record packed with further personal revelations, anecdotes, and lessons. — Danielle Chelosky


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195. No Age – “Teen Creeps” (2008)

The LA duo’s knack for writing incredible earworms is one of the many reasons that they belong on this list, and more specifically, why “Teen Creeps” belongs on this list. A noisy, chaotic, overflowing song that brims with emotion, “Teen Creeps” is an anthem that spares no listener. This track rips open a conversation about people who “wash away what we create,” it’s raw frustration at these teenage creeps who don’t know what they’re getting into – what No Age has been a part of for a long time. — Happy Haugen


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194. Air – “Cherry Blossom Girl” (2004)

Moon Safari put Air on the map back in 1998 and features their biggest singles, but Talkie Walkie might be their best album. The duo’s maturity shows in eschewing all awkward tonal changes in favor of a refreshingly mellow atmosphere throughout. The album doesn’t come without knockout singles though, and “Cherry Blossom Girl” fits that bill. Producer Nigel Godrich (Radiohead, Beck’s Sea Change) had some expertise in fleshing out a song’s palette while maintaining that pleasant ambient atmosphere, and it’s not merely speculative to assume the flutes, bowed vibraphone, and additional vocals were deftly added into the mix under his guidance. — Andrew Cox


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193. Sean Paul – “Get Busy” (2002)

When you’re seven years old and forced to listen to whatever is on pop radio in the backseat, a voice like Sean Paul doesn’t exactly register as impactful or game-changing. “Get Busy” and “Baby Boy” were just the next chart-topping hits in rotation with “In da Club” or “Lose Yourself.” Yet it’s that sense of normalization that is impactful long-term. In the seventeen years since Sean Paul topped the charts, I and all those kids bobbing their heads in the backseat have grown to adulthood. To us, Jamaican dancehall isn’t an acquired taste or seen as something only a certain segment of the population cares about. We see Sean Paul and that he was the most important figure in making dancehall an ingrained part of American music. — Andrew Cox


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192. MGMT – “Electric Feel” (2007)

As I think MGMT intended, there is an energy to “Electric Feel” unlike any other. It currently resides at the top of my “songs to dance to like it’s 2013” playlist on Spotify, which I created to take me back. Alongside “Rollercoaster” by Bleachers and “Tongue Tied” by Grouplove, this song soundtracks any and all parties and late night drives of my youth. As I flail my arms and bob my head in sync with friends and strangers alike in someone’s basement, I feel understood and released. It is not just that it builds, but that it carries a rhythmic punch throughout. I think this is why it played a key role in many important pop culture moments in 2008: Tony Hawk’s much-awaited spin-off video game Tony Hawk: Ride, S2:E4 of Gossip Girl, and Christian Dior’s Ready-to-Wear show for his spring 2009 line. — Sadie Burrows


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191. Art Brut – “Formed a Band” (2004)

Art Brut has become one of those “Hey, remember ____?” acts for indie music fans of past generations, but for this listener who only found out about them in recent years, this band still puts a smile on your face. Bang Bang Rock & Roll is full of short jams with lead singer Eddie Argos displaying his wry personality through punkish vocals. “Formed a Band” is their M.O. in three minutes: “Formed a band / We formed a band / Look at us! / We formed a band!” They set high expectations by proclaiming they will write a perfect song that will unite the world. Well, at least “Formed a Band” is perfect. — Andrew Cox


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190. M.O.P. – “Ante Up (Robbin Hoodz Theory)” (2000)

If you need an old school rap exercise playlist, right after LL Cool J’s “Mama Said Knock You Out” should be M.O.P.’s “Ante Up.” Few songs are as successful as an adrenaline boost; it makes you want to suplex somebody for no reason. For the Brooklyn duo, there’s no time for chit-chat or moral quandaries — Ante up! East coast hip-hop embraced the song immediately as Busta Rhymes and Remy Ma jumped on a remix, and Gang Starr and Method Man make a cameo in the music video. It’s now a go-to soundtrack for mediocre comedies like 30 Minutes or Less, The Mindy Project, and Brooklyn Nine-Nine. — Andrew Cox


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189. Florence + the Machine – “Dog Days Are Over” (2008)

I can’t listen to Florence + the Machine without thinking of this song, summer, and my friend Hannah. The first two are obvious associated thoughts with one being a top hit of English indie rock band and the second being a reference of the song. The last of that list is because of a t-shirt my freshman year roommate turned long-time pal wore often those first few months of college. Within the first moments of meeting, Hannah expressed her love of Florence — her voice, her look, her everything. I didn’t get it. I had only heard a few of her songs and found them to be a bit too avant-garde for my liking. But with her classic loving push, Hannah made me listen again (and again and again). It only took one car jam session for me to recognize her brilliance. “Dog Days Are Over” takes a look at joy and its implications unlike any other song I have heard. Florence’s airiness is only topped by the surprising depth of power in her voice. The production includes everything from playful stringed instruments to heavy bass drum, and makes the experience irreplicable and wonderfully overwhelming. Because of these reasons, this song is still their most played song on Spotify by a large margin, and I imagine it will remain that way throughout the band’s lifetime. — Sadie Burrows


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188. Air France – “Collapsing Outside Your Doorstep” (2008)

For a solid four years, the Swedish record label Sincerely Yours released nothing but essential indie pop releases. The label specialized in a new version of Balearic beat (named after the Ibizan island) that incorporated New Wave and sampledelia elements. Memory Tapes, jj, The Tough Alliance/CEO, Kendal Johansson, The Honeydrips, and Air France all had releases that garnered praise from Pitchfork and other indie outlets. Out of all of them, Air France has best stood the test of time with “Collapsing Outside Your Doorstep” with the ever-intoxicating sample refrain “Sort of like a dream, isn’t it? No, better.” — Andrew Cox


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187. Young Jeezy (ft. Jay-Z) – “Go Crazy (Remix)” (2005)

Young Jeezy sounded every bit of 28 years old when he broke big, but he would keep the “young” moniker well into his 30s. “Soul Survivor” gave Jeezy his only top-five hit, but he ceded the spotlight to Akon on the hook. “Go Crazy (Remix)” was released right after and couldn’t make the top twenty on the rap charts. The Cannon beat is one of his best, and Jeezy spits out his anthem over it. Jay-Z doesn’t overshadow him with his great verse but rather solidifies Jeezy’s status as a new leader in the hip-hop scene. Even if he hasn’t since matched up to his debut, Jeezy has become synonymous with the idea of street cred in hip-hop with his whole persona defining a path to success without sacrificing any harsh edges. — Andrew Cox


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186. Lil Mama – “Lip Gloss” (2007)

The percussive, booming, in your face characteristics of the introduction to “Lip Gloss” either entice a first time listener or bring to mind the other thousands of times they’ve jumped out of their chair at the first beat. Lil Mama’s hit from her debut is punchy and effective, and connected to fun memories for many. Her brand of hip hop is electrifying and addictive, resulting in an irresistible and empowering anthem. Accompanied by a knockout music video, her beats and catchy rhythms leave the listener energized and ready to conquer their high school halls, or whatever setting they may be in. — Virginia Croft


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185. U2 – “Beautiful Day” (2000)

It’s been 20 years since U2 released the optimistic anthem “Beautiful Day,” and yet we need its message of hope now more than ever. Bono said it’s about “a man who has lost everything, but finds joy in what he still has,” and even skeptics can agree our frontman is very convincing as he cries out, “It’s a beautiful day, don’t let it get away.”

Considering the song is a bona fide morale booster, I’d like to think that had Apple and U2 gifted it to millions of iTunes accounts without permission today, we’d welcome the “intrusion.” After all, who couldn’t use a forced dose of positivity right now? — Leslie Richin


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184. Daddy Yankee (ft. Glory) – “Gasolina” (2004)

Puerto Ricans are Americans. Indisputable truths like this have to be said constantly, especially after this country’s pathetic response to the devastation of Hurricane Maria in 2017. The story of Puerto Rican music therefore is also an American story with figures like Tego Calderón and Daddy Yankee who should be treated as national treasures. The latter has been in the limelight for nearly two decades inspiring the new wave of Latin trap leaders like Bad Bunny. “Gasolina” is Yankee’s most enduring classic, which had major crossover success in the mid-’00s. Through Luny Tunes’ electrifying production and Yankee’s forceful delivery, Reggaeton finally earned some respect and the fruits of their labor can be seen in the current musical climate. — Andrew Cox


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183. Basement Jaxx – “Where’s Your Head At?” (2001)

I feel like I write the same narrative with Basement Jaxx every time — ‘they should be more popular;’ ‘they’re cartoonish in the best way possible;’ ‘Rooty holds up in every way imaginable.’ “Where’s Your Head At?” is their most popular track at least, and I want to believe I’ve heard it in some capacity recently outside of myself seeking it out. If you’re listening properly, it’s impossible to not bob your head. Of all the songs on this list, it might be the most high-octane of all; it’s easy to lose track of how many voices pop up and all the different ways the song’s title is shouted. My favorite voice is the one that goes “You have now found yourself trapped in the incomprehensible maze” halfway in; the only way out of this madness is straight through. — Andrew Cox


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182. Gorillaz – “Feel Good Inc.” (2005)

When I first heard this song (on a TV!), I was years away from being able to place Del La Soul, Damon Albarn, or Danger Mouse. I was just a kid who knew a good song when he heard it, and “Feel Good Inc.” is undeniably good. Built around a boinking bassline and a refrain that implores you to “feel good,” Gorillaz’s biggest stateside hit is—like a smiling man with a gun to his back—imbued with a dreadful sense that something deceptively wicked is underway. (The evil laughter that appears throughout isn’t exactly subtle in its implications.) — Alex Wexelman


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181. Nelly Furtado – “Maneater” (2006)

On her first two albums, Canadian singer Nelly Furtado established herself as an adult contemporary darling who blended elements of folk and R&B. On her 2006 project, Loose, that all changed with tracks like “Maneater.” The single, much like its predecessor “Promiscuous,” is a full on electropop jam that incorporate aspects of hip hop. Featuring peppy, pulsing beats and deep, dirty synths, it is the kind of song that is fit for both crowded clubs and solo dance parties in your bedroom. With Furtado’s brash vocals and Timbaland’s big production, “Maneater” is a track that not only gets people moving but also instills confidence. — Drew Pearce


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180. The New Pornographers – “The Laws Have Changed” (2003)

Taken from their revered second LP, 2003’s Electric Version, “The Laws Have Changed” epitomizes why The New Pornographers is one of the best indie rock/power pop bands of their era. It’s direct and concise, yet also nuanced enough to feel idiosyncratic and curious. In a way, it’s emblematic of the prevailing late-‘90s/early-’00s radio-friendly aesthetic, but there’s also a tinge more-luscious 1960s Brit pop playfulness thrown in, too. Plus, the male/female harmonies and vocal trade-offs add sleek dynamics, solidifying why its punchy-yet-fun edge made it perfect for inclusion on the soundtracks to Weeds and Gilmore Girls. — Jordan Blum


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179. Aphex Twin – “Avril 14th” (2001)

While many of the essential songs of the 2000s are powered by strong, poetic vocal verses, Aphex Twin’s “Avril 14th” is strictly instrumental. However, it still feels just as impactful as its counterparts. Overall, the song can be a bit misleading, as the majority of Aphex Twin’s musical works are heavy on the electronic side and typically more intense than “Avril 14th” ever lets on. Standing alone as a glitch in his discography, Aphex Twin creates a beautiful, melancholic two minutes of almost tear jerking piano music. The melody is rich and soothing, shimmering in its graceful presentation, enveloping the listener in a shield of new hope. — Virginia Croft


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178. Ciara (ft. Ludacris) – “Oh” (2004)

Just like the South overtook hip-hop in the mid-’00s, r&b incorporated Southern Crunk elements as a natural evolution of the genre. Ciara was at the front of this Crunk&B subgenre with her debut album Goodies; the first three singles off that album reached the top two on the Billboard singles charts. “Oh” doesn’t have the obvious hook of the other two hits, but it’s the one with the most going for it. Ciara is a more forceful presence on the mic with a heavier rap cadence, and the production from Dre & Vidal serves her better through subtlety rather than Lil Jon’s typically heavy-handed work on “Goodies.” — Andrew Cox


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177. Luomo – “Tessio” (2000)

Vladislav Delay has released many albums under different pseudonyms, but Vocalcity as Luomo remains the most essential. If there’s any indisputably classic album from the decade that I fear may be lost upon the next generation of music criticism, it might be Vocalcity. Albums that define electronic subgenres are only as beloved as that subgenre remains, and I wouldn’t bet on microhouse (coined by Philip Sherburne) moving the needle much today outside of diehard music lovers and some dedicated music critics. With “Tessio” off Vocalcity, Luomo offered up the best display of microhouse’s subtle euphoria. He combined the anthemic rave spirit of ’80s House DJs with the glitchy IDM technical skill of ’90s producers for a distinct brand of electro-pop that has shown no signs of aging. — Andrew Cox


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176. John Mayer – “No Such Thing” (2001)

Before John Mayer was touring with Grateful Dead, he was a young and enthusiastic guitarist, new to the scene in 2001 with his first major studio album Room For Squares. The opening track “No Such Thing” is a cathartic, acoustic guitar-driven track that secured his place as a hitmaker. Its lyrics cheerfully state that the idea of a ‘real world’ is arbitrary, which was the 21-year-old John Mayer’s way of saying he is going to do whatever the f— he wanted. Which he proved, later in his career, as he branched out to new genres….and got in his fair share of trouble. — Nina Braca


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175. Johnny Cash – “Hurt” (2002)

With all due respect to Nine Inch Nails, few songs quite embody the idea of a cover song that’s better than Johnny Cash’s rendition of “Hurt.” Here we have Cash — in the twilight of his life and by his admission — a reformed man of God, taking lyrics about suicide and depression and turning it into a song about self-reflection and modesty in the hope that we can all be more than our wrongdoings. Accompanied by a beautifully-subtle arrangement that features little more than an acoustic guitar, “Hurt” is as much heart-wrenching as it is beautiful. Coupled with the fact that Cash and his wife June would pass away just a year after the songs release, it’s hard not to believe the revered country singer was given privileged listeners a look into the mind of a dying man. Cash lays himself bare, and in turn creates one of his greatest pieces of work. — Clay Sauertieg


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174. Destroyer – “Painter in Your Pocket” (2006)

The mythos of Dan Bejar has steadily grown since 2011’s Kaputt, a soft rock magnum opus that has converted many to the Vancouver singer/songwriter’s singular style. Five years earlier though, he made another classic album with Destroyer’s Rubies, and it’s more in line with his New Pornographers’ work. “Painter in Your Pocket” has become his definitive non-Kaputt track as the acoustic guitar riff and Bejar’s lyrically-dense chorus are captivating on every listen. For those put off by Bejar’s oft-pretentious aesthetic, this song acts as a relatively-simple folk rock delight. It’s a good reminder that intelligence doesn’t always have to be sacrificed for easy melodies. — Andrew Cox


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173. Byrne & Eno – “Strange Overtones” (2008)

In the grand legacies of both David Byrne and Brian Eno, this song might’ve flew under your radar. Their first collaboration in ’81 (My Life in the Bush of Ghosts) remains a perplexing classic, but 27 years later, “Strange Overtones” became one of the most accessible works either had ever done. Byrne finds inspiration in a meta-narrative where he overhears a neighbor trying to write a song that is “out of fashion.” Though the song’s arrangement does feel beamed in from another time, their collective vision for art pop is a timeless thrill ride. Byrne also writes one of his best lyrics with “See the music in your face that your words cannot explain.” — Andrew Cox


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172. T.I. – “Rubber Band Man” (2003)

If there was ever a song meant to be blasted from car windows on a hot summer day, it’s “Rubber Band Man.” Before trap had become so ubiquitous the term essentially became meaningless, T.I. crafted a hustling anthem for the ages, one that goes off like a grenade from the start and keeps on exploding without losing its power. A blaring organ motif from David Banner and T.I.P.’s verses and choruses each rolling into a smorgasbord of triumph made his ascendance inevitable. Because no one with this much hunger and presence was going to accept being left out. — Brody Kenny


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171. Alicia Keys – “Fallin'” (2001)

Alicia Keys was to the ’00s as Mary J. Blige was to the ’90s — a hugely successful leader in r&b with hits that were emotional powerhouses while remaining comfortable to a mainstream audience. “Fallin'” was her first single and a perfect choice as it showcased her serene piano playing and impressive vocal range. It took a few months for the song to lift off, but it would eventually end up the second biggest song of 2001 according to Billboard behind Lifehouse’s “Hanging By a Moment” (not on this list). With “No One” and “Empire State of Mind,” Keys quite possibly became the voice of her generation, but the first single is still where she sounds most natural. — Andrew Cox


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170. Eminem – “The Real Slim Shady” (2000)

It’s the lead single from Eminem’s deservedly successful—and controversial—third record, 2000’s The Marshall Mathers LP. Its value as a deceptively clever tongue-in-cheek satire of popular culture—alongside biting commentaries on Mathers’ rise to fame, ridicule, and condemnation—are even more salient in retrospect. In other words, its dated references have become increasingly charming as time capsules of a nostalgic period for many of us (myself included since I was thirteen years old at the time). Musically, it’s still catchy as hell and full of quirky moments as only Eminem could deliver, and the then-ubiquitous music video remains pure oddball gold. — Jordan Blum


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169. Arcade Fire – “Rebellion (Lies)” (2004)

A hit on a critically-acclaimed album full of hits, “Rebellion (Lies)” has aged like a fine wine. Much like its title, the song is a wonder rebellion, or escape from an otherwise chaotic world around it in 2004. Perhaps in an ode to French philosopher Albert Camus, Arcade Fire and lead singer Win Butler conclude on the track that if the world is chaos and we all must die, the only thing we can do is to rebel. Butler sings of the lies society tells (“People say that you’ll die, faster than without water”) as well as society’s view of sexual norms (“Come on hide your lovers, underneath the covers”) and then encourages listeners to wake up and live life in spite of these factors (“Sleeping is giving in, so lift your heavy eyelids”). The song is a beautiful ode to those who acknowledge the absurdity and harshness of the world and yet wake up to face it each day. — Clay Sauertieg


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168. blink-182 – “I Miss You” (2003)

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Early-’00s playlists are not complete without blink 182’s “I Miss You.” This song was the second single from the blink 182, the band’s self-titled fifth studio album in 2003. Although “I Miss You” didn’t reach the same acclaim as “All The Small Things,” the former was still certified Gold by the RIAA.

The macabre lyrics coupled with the easy-going and upbeat rock instrumentation make for a wild juxtaposition. The song’s timelessness does stem from its lyrics, though. Fans and critics alike regard “I Miss You” as a classic break-up song.

“Hello there / the angel from my nightmare / the shadow in the background of the morgue / the unsuspecting victim / of darkness in the valley”

Even more iconic is the eerie music video that accompanies “I Miss You.” The opening scenes follow a woman (or ghost) in a ballgown that’s wandering around a tudor mansion — creepy!

blink 182’s discography often scored 2000’s culture; their music underlined hit shows, video games and movies. This single rose in prominence again after being included as downloadable content for the popular game Rock Band II. — Chanell Noise


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167. Los Campesinos! – “You! Me! Dancing!” (2007)

I’m pretty sure this is not common knowledge, so I’ll go ahead and say it: Los Campesinos!’ Hold On Now, Youngster is one of the best indie rock albums of the decade. Even if you don’t want to accept that, you have the album’s centerpiece “You! Me! Dancing!” to act as a sampler. The song was a holdover from their debut EP Sticking Fingers into Sockets, and that version might be the better one as it gets to the actual song about thirty seconds quicker (hey, I like noise rock but getting to the point is nice, too). If the instrumentation wasn’t jubilant enough, the message drives that point home: there’s you, there’s me, and there’s dancing! — Andrew Cox


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166. Nelly – “Hot in Herre” (2002)

This song’s more of a novelty than the big singles off Country Grammar and less popular than the Kelly Rowland-featuring “Dilemma,” but Nelly was never more fun than here (“herre”) with his comical lyricism. Who doesn’t shout out “I think my butt gettin’ big!” when the music drops out. The song may have been ruined by being accepted into White suburban circles as a joke like it’s “Baby Got Back” or “Can’t Touch This,” but Nelly had a dynamite aesthetic early in his career that makes “Hot in Herre” — and every major hit of his at the turn of the century — so electrifying. — Andrew Cox


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165. Fever Ray – “If I Had a Heart” (2008)

Fever Ray’s work with xer brother in The Knife resided often in dark corridors, but xer solo work proved to be downright terrifying. “If I Had a Heart” works like the opening credits with a long trek into a setting with no escape. The song’s brilliance is in its absence of a climax or any type of sacrifice towards mainstream appeal. Despite that, the song has become the most well-known of xer solo work and is only behind “Heartbeats” when you consider everything Dreijer has worked on. It is a go-to mood-setting piece used as the credits song for Vikings, and it also appeared in Breaking Bad. — Andrew Cox


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164. The Rapture – “House of Jealous Lovers” (2002)

DFA Records pumped out hit after hit to kick off the 21st century with the “Deceptacon” remix, the early LCD Soundsystem singles, and the Rapture’s “House of Jealous Lovers.” The label led the reviving dance-punk scene with a deft ear for propulsive, cymbal-heavy 4/4 percussion and snarling attitudes, and The Rapture best conveyed that sound. “House of Jealous Lovers” has nothing complex going on, but each bassline, guitar riff, and cowbell is executed perfectly. They’re so confident in the sound that they spend an inordinate amount of time just counting to eight. They had every right to goof off with the lyrics. — Andrew Cox


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163. Modest Mouse – “3rd Planet” (2000)

Modest Mouse’s third album, The Moon & Antarctica, was the first released for a major label (Epic Records) back in June 2000. “3rd Planet” is the first track, opening the album with some simple acoustic plucking, before diving head-first into the distorted guitars, lo-fi vocals, and philosophical lyrics that the band is notorious for. Though never released as a single (none were released for the album), “3rd Planet” stands as one of the most popular tracks and is certainly one of their best. The lyrics can be interpreted many ways, and as they should when they span the entirety of time and space. — Nina Braca


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162. Three 6 Mafia (ft. UGK & Project Pat) – “Sippin’ on Some Syrup” (2000)

Lean has its beginnings in Houston. Blues musicians would mix Robitussin with beer back in the ’60s, and by the ’80s/’90s, codeine cough syrup became the base. DJ Screw and UGK rose to fame out of Houston at this time, and references to this concoction was a requirement for Southern hip-hop. The greatest ode to lean came from Memphis’ Three 6 Mafia at the turn of the century, and of course, they had to turn to UGK to embolden the message. This classic brought the drink to a nationwide audience, and the hook and pronunciation of syrup (“sizzurp”) particular stick in the mind. Purple drank would also reach a wider audience due to DJ Screw and Pimp C both dying with lean in their system. It might be best to focus on the sense of community and cultural pride that lean stands for in a song like this rather than dwell on its dangers. — Andrew Cox


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161. Cat Power – “I Don’t Blame You” (2003)

“I Don’t Blame You” has a special place in Chan Marshall’s discography. She recorded it solo as the last song on You Are Free, her greatest album. It ended up opening the album and was almost released as an official single. Marshall has cited this song as her favorite to perform live, and even though the narrative focuses on a third-person character, she must see something in this character performing for herself primarily and feeling like she has a duty to appease her audience. There’s an empowering message here due to Marshall being the calming voice with no judgement for whomever needs to engage in artistic ventures without a supportive audience. — Andrew Cox


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160. Erykah Badu – “Didn’t Cha Know” (2000)

J Dilla’s production, with a looping bass sample from Tarika Blue’s “Dreamflower,” forms the basis of one of Erykah Badu’s most contemplative and gorgeous songs. Mama’s Gun standout “Didn’t Cha Know” works great in multiple contexts, whether in isolation, as a more reserved followup to the fanfare of album opener “Penitentiary Philosophy,” or through the majestic video, with Badu and her iconic outfit trekking through the desert. The most attention, though, should fall on her voice and how she morphs the confrontational and confessional. Badu knows how to show strength through facing setbacks, even if she’s not certain about any one solution. — Brody Kenny


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159. Kanye West (ft. Dwele) – “Flashing Lights” (2007)

Even though nobody would say Kanye’s discography has been overlooked these last fifteen years, I do believe Graduation — the peak of Kanye’s commercial success — is a bit undervalued. The singles off this album are the most extravagant of his career with “Flashing Lights” being the most radiant of all. The glowing synth beat is to die for and the use of strings here would be his best until they would pop up all over the place on My Beautiful Dark Twisted Fantasy. The production and Dwele’s chorus does the heavy-lifting here, but Kanye’s second verse is one of his best displays of affable wordplay. — Andrew Cox


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158. Pulp – “Sunrise” (2001)

What a way to go out. We Love Life is still Pulp’s last album, and the final song on it had the ironic title of “Sunrise” — an allusion to new beginnings and looking forward to what’s ahead. The song was certainly a change of pace for the band as Jarvis Cocker’s prolix charisma is not necessarily the draw here. “Sunrise” begins a little innocuous and seemingly an odd choice for a lead single, but halfway in, the sun rises. This guitar solo for the ages with a heavenly choral backing should jolt anybody out of slumber. After a bit of rest, it starts all up again as a complete duplicate. It’s like the end of a concert where the lead singer walks off first. The true encore may never happen. — Andrew Cox


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156. Band of Horses – “The Funeral” (2006)

A powerful, melancholic ballad, Band of Horses’ standout track “The Funeral” leaves a residue of sorrow and an urge to be our best. It has been featured in an extensive selection of films and TV, including Gossip Girl, The Stepfather, and 127 Hours. The music video tells a story of despair that matches the blue tone of the track, centering on a man whose dog has died, drowning his sadness in alcohol. “The Funeral” is a beautiful track, taking a moment to pause on all of the complexities of life, and to simply breathe in, and reflect through the hardness. — Virginia Croft


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156. Arctic Monkeys – “A Certain Romance” (2006)

Proving to be the most rewarding and complex listen on their debut Whatever People Say I Am, That’s What I’m Not, “A Certain Romance” paints a picture similar to the ups and downs of a love story. Weaving in and out between a raucous intro and slower, more subdued sections, the song is a whimsical dive into the intersection of slacking off and realizing it’s good to hold on to what you’ve got. As Alex Turner examines his peers in his town, he eventually switches from scoffing at them to cutting them some slack, and that in itself is a very specific brand of romance. — Virginia Croft


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155. Dizzee Rascal – “Fix Up, Look Sharp” (2003)

On his debut, Boy in da Corner, young London rapper Dizzee Rascal sounded like a polished MC and his own hype man. He deserved the self-congratulation, especially with efforts like “Fix Up, Look Sharp.” Centered around a sample of Billy Squier’s “The Big Beat,” “Fix Up, Look Sharp” twitches and squeals with the energy of someone who has been cooped-up for far too long. Dizzee addresses his hype and asserts that he’s going to live up to it, which would be clear even without his boastful lyrics. This may have been the first real taste of UK hip-hop that many got, but for anyone with good judgment, it wasn’t the last. — Brody Kenny


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154. OutKast – “So Fresh, So Clean” (2000)

The three singles from Stankonia amount to some of the weirdest, most jubilant hip-hop classics ever made. “So Fresh, So Clean” is the most straightforward of them though that’s an easy achievement against the other two. Big Boi takes the first two verses outlining what is considered fresh and clean (Rollo from Samford and Son, Teddy Pendergrass, Sevilles and Monte Carlos, etc.), while André 3000 weirds out with talks of Anne Frank and malnutrition. Sleepy Brown is the uncredited vocalist on the hook here; he would later assist on “The Way You Move.” — Andrew Cox


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153. Jay Reatard – “My Shadow” (2006)

“My Shadow” is the perfect song that captures Jay Reatard in three minutes and eighteen seconds – fast, loud, raw, catchy: these are what made him the legend he is today. “My Shadow” is played at breakneck speeds with a constant palm muted guitar acting as the heartbeat of the song, and the chorus is guaranteed to get stuck in your head for the rest of the day. Eventually, you’ll find yourself coming back to it again and again, just to hear the raspy “my shadow! My shadow!” because for whatever reason, it’s enticing. Jay Reatard was an enticing person – who knew what he would do or say on stage – and thrill of a Jay Reatard show is the same thrill on “My Shadow.” — Happy Haugen


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152. Queens of the Stone Age – “No One Knows” (2002)

Although QOTSA’s second LP—Rated R—was their breakthrough release, its successor, Songs for the Deaf, truly propelled them into mainstream consciousness. Intentionally or not, its faux radio broadcast gimmick was a novel nod to The Who Sell Out, and much of its acclaim was due to the hypnotic appeal of “No One Knows.” Led by the trademark percussive precision of Dave Grohl (whose breakdowns during the chorus are exceptional), its sharply enticing guitar riffs and anthemic melodies made it the band’s most accessible and irresistible song yet. All these years later, they’ve likely never topped it in that respect. — Jordan Blum


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151. Sleater-Kinney – “Modern Girl” (2005)

A song as spritely as “Modern Girl” can feel a bit incongruous on Sleater-Kinney’s initial finale, The Woods. After so many crushing anthems with powerhouse guitars, this Carrie Brownstein-led breather might seem better suited for skipping, whether it’s skipping past to the might of “Entertain” or literally just skipping along to in a field. However, Sleater-Kinney are terrific pop songwriters in any context, and just because they’ve turned down the amps doesn’t mean they’ve turned down the energy. “Modern Girl” still has plenty of grit, both in its shows of distortion and how Sleater-Kinney uses ’60s girl group stylings to wryly comment on consumerism and malaise. By the time it’s over, you ought to recognize exactly how essential it is. — Brody Kenny