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100. Grizzly Bear – “Two Weeks” (2009)

With a mellowed, quiet vocal line, Grizzly Bear’s “Two Weeks” focuses on the demise of a relationship, its instrumentals mimicking the confusion and despair that the experience brings. Victoria Legrand of Beach House supplies background vocals, adding another layer of melancholy to the dreary landscape the Brooklyn band painted. Right from the start, Ed Droste sings, “Save up all the days / a routine malaise,” incorporating the concept of having an uneasy feeling, with an origin that is nearly impossible to identify. “Two Weeks” explores this malaise, branching out into uncomfortable territory, but the lessons learned make it all that much more worthwhile. — Virginia Croft


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99. Paramore – “That’s What You Get” (2007)

Instantaneously, I am invested. I want to close my eyes and just soak in this now well-known intro to this 2007 pop punk hit. I am quickly lost in the sensation of the song, but I am stopped when I realize the true sadness behind the lyrics. Paramore does this. They consistently release music filled with poetic tragedy that feels fun because of the pounding drums or resonating electric guitar. I am left in this state of confusion, ultimately choosing to let go and just enjoy the genius expression of feeling. It is as unnerving as it is fulfilling. With this particular track from their (arguably) best album Riot!, the words grasp at this sensation eerily well: “That’s what you get when you let your heart win.” The punk within me nods in agreement; my head bobs to the beat. — Sadie Burrows


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98. Mary J. Blige – “Family Affair” (2001)

Dr. Dre’s production footprint did not fade with the turn of the century. He was behind much of Eminem’s work, 50 Cent’s “In Da Club,” and Eve’s biggest hits. The best of them all though was this one-off with Mary J. Blige that went to #1 for 6 weeks at the end of 2001 (Blige’s only hit to do so). It’s a stomping beat fit for royalty, and the r&b queen makes it smooth with her speak-sing style. “Family Affair” is a hip-hop indebted track, and Blige leans into it with words like “hateration” and “holleration.” She also refers to “percolatin'” which might be a reference to a Green Velvet House classic. Either way, she went all out for this one — including all the vocal runs — and it remains her go-to track. — Andrew Cox


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97. Camera Obscura – “Lloyd, I’m Ready to Be Heartbroken” (2006)

If the indie pop comes from Glasgow, you just know it’s going to be a little more elegant than what we get in the states. You throw in recording in Sweden, and it should be off the charts. Camera Obscura had already worked with Belle & Sebastian’s Stuart Murdoch for their first album, and by their third, they were working with The Concretes’ producer Jari Haapalainen. Let’s Get Out of This Country would end being their best album with lead single “Lloyd, I’m Ready to Be Heartbroken” being their signature song. Lloyd refers to Glasgow’s Lloyd Cole and his song “Are You Ready to Be Heartbroken?” With the help of a chamber organ and a delightful string arrangement, Camera Obscura found their complete sound. — Andrew Cox


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96. The White Stripes – “Fell in Love With a Girl” (2001)

Jack White, perhaps inadvertently, creating a pop rock jam was not something White Stripes listeners may have anticipated in 2001, and yet here we are. Clocking in at just under two minutes, the song is concise, simple, raw, happy and witty. Pair those simple lyrics with a snappy guitar line and White’s wailing, whiny vocals, and what you get is a song that listeners can’t help but sing along and dance to. It’s perhaps the most infectious, energy-filled song in Jack White’s storied catalogue and has had impressive staying power in terms of popularity. — Clay Sauertieg


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95. Vampire Weekend – “Oxford Comma” (2008)

My love and experience of Vampire Weekend has grown exponentially since my first exposure to them, with the release of their most recent album Father of the Bride fully cementing my need to meet and intimately embrace Ezra Koenig. Yet, I cannot shake my first memory of them. I was 13 and one of my idols was my neighbor Meredith. She was a year older and, therefore, I perceived her to be better in about a hundred ways. It was on a Friday morning bus ride that she shared her incredible life experience with me. The night before she had attended a concert at a local venue with her even cooler older brother and his girlfriend. Everything about the event grew my envy. In my mind, that was the pinnacle of the teenageness I aspired to reach so badly, so quickly. “Who did you see?” I asked without much knowledge of anything musical outside of church hymns. The answer: Vampire Weekend. I sprinted down my driveway, flung open my laptop, and hit play. My exploration of their music covered their first two albums. I remember thinking it was weird, but also good. It had to be if Meredith liked it. Ever since, my image of Meredith, her brother, and the girlfriend at the concert is the same as the artwork for their self-titled first full-length release: the tops of heads, a pink ceiling, and an intricate chandelier. “Oxford Comma” still sits near the top of my list of favorite Vampire Weekend songs. Titled after one of my favorite grammatical elements, it is unique, referential, and strong-standing as a pillar of that trademark Vampire Weekend sound we all love and follow. — Sadie Burrows


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94. Phoenix – “1901” (2009)

In 2009, it was impossible to walk into a mall without hearing the upbeat synths of “1901” by indie pop band Phoenix. Off their critically-acclaimed fourth studio album “Wolfgang Amadeus Phoenix,” the track was the first of theirs to chart in the United States, skyrocketing them to mainstream popularity. The track was a perfect summer anthem, with the urgency of the pre-chorus building up to the repetitive “fold it fold it fold it.” The song was seemingly made to just be a perfect sing-along driving anthem. — Nina Braca


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93. Gwen Stefani – “Hollaback Girl” (2005)

“Hollaback Girl” is the “We Will Rock You” for middle school girls of the early 2000s and I mean that as a compliment. Not only is it an incredible piece of pop music; it also taught a generation how to spell the word bananas. Those horns, the syncopated beat, the cheerleader style chanting—everything about this earworm is classic Pharell. But Gwen brings attitude. She’s ready to attack, gonna lead the pack and she is prepared to fight. The song is purported to be a response to a feud with rock star Courtney Love proving rivalries can sometimes be fruitful.  — Alex Wexelman


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92. M83 – “Don’t Save Us from the Flames” (2005)

M83 is known for their incredible genre-bending abilities and evoking a sense of wonder from the listener with their synth-based tracks that create an extraordinary listening experience. Despite the ominous and dark subject matter and song title, “Don’t Save Us from the Flames” rings true to that wondrous sensation – after an introductory drum fill, the French electro-pop duo creates a sensation of flying amongst the stars, and then tells the story of a couple who suffered a fiery car accident. The lyric writing is incredibly descriptive, almost too descriptive. Lines like “out of the flames/a piece of brain in my hair,” and “bleeding all around/liquid metals through my veins” create a severe scene that confuses someone who’s listening. “Don’t Save Us from the Flames” sounds upbeat and energetic, but is dimmed once the lyrics are understood – creating a certain emotion that can only be described as an M83 song. — Happy Haugen


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91. Morrissey – “First of the Gang to Die” (2004)

Morrissey’s solo discography is spotty, never reaching the highs of The Smiths, but he has been consistent though with an occasional great single. Over fifteen years into his career, “First of the Gang to Die” is the best of them all with a nonstop melodic drive and Morrissey’s bleak romantic persona in full force. If you don’t dramatically pantomime lines like “Such a silly boy” or “smashed human bone,” then what’s the point of listening to Morrissey? Everything’s gone downhill for him since he’s shown his true character, but nothing can strip away the joy of his best work. — Andrew Cox


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90. Santigold – “L.E.S. Artistes” (2008)

For at least one year, Santigold was the biggest name in indie pop — a fellow leader in the genre amalgamation movement led by M.I.A. around this time. Along with “Lights Out,” “L.E.S. Artistes” saw Santigold incorporating electro-punk and new wave sounds into perfect 3-minute jams that were bound to hold up for eternity. Santigold worked with John Hill for production and instrumentation on the track and many others on the accompanying album. Hill would later be nominated for two Producer of the Year awards at the Grammys, having his hands all over ’10s pop radio including Portugal. The Man’s “Feel It Still.” — Andrew Cox


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89. Wilco – “I Am Trying to Break Your Heart” (2002)

With “I Am Trying to Break Your Heart,” an American classic begins. The first track on Yankee Hotel Foxtrot, the song introduces a new era of the band. Their previous album, Summerteeth, was their take on Kinks-like powerpop; YHF is a freaky carnival á la Sgt. Pepper’s. Percussion makes up a bulk of the track’s palette. There are some dark horns that underpin everything, especially Jeff Tweedy’s Dylan-esque impressionistic lyrics, which I do not advise looking up on Genius. (What makes the words special is the sense that they are imagistic and not a story; see Kevin Young’s poem of the same name.) — Alex Wexelman


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88. Bill Callahan – “Jim Cain” (2009)

No matter what personnel is involved in the making of his songs, Bill Callahan always sounds alone. And not just in the studio or in his living room — more like an open field, a small creek, a dusty pleateau. His ability to transport the listener outside of the technical fussiness behind every song’s production and purely into the landscape of his lyricism is unmatched. “Jim Cain” was the opening track off his first album as just Bill Callahan (he released eleven albums as Smog) and it justifiably focused on reinvention but only as plainly as Callahan could state: “I started out in search of ordinary things.” By the end, a beautiful Callahan trope emerges: sometimes you have to leave because you don’t know where you’re going. — Andrew Cox


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87. Freelance Hellraiser – “A Stroke of Genius” (2001)

A few years ago, I was at an unmemorable hotel resort bar & grill in Orlando, and the opening to The Strokes’ “Hard to Explain” starts playing — alright cool, a classic. Then, Christina Aguilera starts singing “Genie in a Bottle” over it — even better! This wasn’t the first time I heard the classic mash-up, but it’s certainly the only time I ever expect to hear it in public. When the mash-up was first released, UK radio stations played it building the song’s word-of-mouth popularity which got the man behind (Roy Kerr) it a cease and desist order from RCA. Kerr would eventually remix a Aguilera song in ’03 and make a whole damn remix album with Paul McCartney under the name Twin Freaks. The mash-up culture has faded alongside illegal mp3 downloads, but its best results still remain classics. — Andrew Cox


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86. Coldplay – “Clocks” (2002)

When they stole Brian Eno’s Joshua Tree-era production—the sparse sounds that add soft textures; subtle, while managing to take up a lot of space in the mix—Coldplay wasn’t trying too hard to shrug off the U2 comparisons. The arpeggiated piano riff on “Clocks” belongs in the Piano Riff Hall of Fame, right next to the Beethoven one that goes, “da dun da dun.” Chris Martin exorcises self-doubt in the song’s vaguely religious journey toward forgiveness. The theme is exemplified in its best couplet: “Cursed missed opportunities, am I / A part of the cure? / Or am I part of the disease?” — Alex Wexelman


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85. Empire of the Sun – “Walking on a Dream” (2008)

Showing heavy influences of David Bowie and Kraftwerk’s most techno driven albums, Australian duo Empire of the Sun put their best pop foot forward on their hit “Walking on a Dream.” With a glowing, warming foundation of cool synths, the pair conjure up a track that brings to mind warmer days, the way the right amount of sun can shift our perspectives, and the joy of simply feeling better. With vocals that amplify the richness of the instrumentals, the opposing forces blend perfectly. The track is deceivingly upbeat for a subject that can feel very low — grappling with homesickness and the constant need to distract ourselves from the battles within. — Virginia Croft


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84. Fleet Foxes – “White Winter Hymnal” (2008)

This track off of Fleet Foxes’ 2008 self-titled album features a single verse with a fairytale-like narrative of a cold winter’s day covered in snow that is repeated three times. As the six-line verse unfolds, the song becomes a little more haunting, with visions of blood in the snow that is described as harmless as “strawberries in the summertime.” The echo of the layered vocals paints a melancholic movie in the listener’s head, while a laid-back guitar sets the score. The song helped the band gain international recognition, spawning dozens of covers — including some for Christmas-themed albums due to some shaky interpretations of the lyrics. — Nina Braca


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83. The Hold Steady – “Stuck Between Stations” (2006)

For all the rockists complaining about the lack of bands carrying on the legacy of heartland rock, The Hold Steady sure does seem like a blind spot. Now maybe that’s not a fair critique (The Hold Steady are neither as charming as Springsteen nor as smooth as Mellencamp), but rollicking pianos, gnarly guitar riffs, and tales of Midwest desperation is as recognizable as American rock gets. On the other hand, explicit references to Kerouac characters and John Berryman in the first lines of verses like in “Stuck Between Stations” doesn’t exactly inspire the masses. If that pertains to you, the instrumental magic of Born to Run survives in “Stuck Between Stations,” and it is something to behold. — Andrew Cox


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82. Eminem – “Lose Yourself” (2002)

“Lose Yourself” was, in a sense, the theme song to Eminem’s celebrated biopic, 8 Mile. It released mere months after arguably his best album, 2002’s The Eminem Show, and was instantly beloved. Twenty years later, it remains one of his most irresistible, purposeful, and relatable tracks, with an enigmatic guitar riff guiding hypnotic beats, a catchy chorus, and typically biting verses. Sure, the “mom’s spaghetti” line has spawned countless memes, but it’s hard to deny how much the song showed mainstream audiences—many of whom previously dismissed or rallied against him—that Eminem could be extremely clever, tuneful, and confessional. — Jordan Blum


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81. Britney Spears – “Toxic” (2003)

The sampled Bollywood strings build drama and announce Brtiney’s single “Toxic” as an event. The spaghetti western guitars and lyrics about danger brought on by a poisonous love affair are dramatic. This high-wire act recalls a James Bond theme. Every inch of this thing is crammed with melodious hooks; you can almost hear Kylie Minogue kicking herself when Spears sings, “I need a hit / Baby, give me it.” The ‘love is a drug I’ve been looking’ for metaphor isn’t new, yet yearning is a powerful emotion, one that is universal. It draws you in like a drug and then you’re on a ride. — Alex Wexelman


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80. Basement Jaxx – “Romeo” (2001)

One of the unsung heroes of UK dance music is Kele Le Roc. She had two solo top 10 UK hits in the late-’90s, but her biggest and best success was her feature on Basement Jaxx’s “Romeo.” It’s a vocal performance as impactful to the song’s greatness as Romanthony (RIP) was to Daft Punk’s “One More Time.” She handles every production change with grace, and that is not exactly the easiest task when dealing with Basement Jaxx. The bridge is the most exciting part as the word count quickly adds up near the end. As the first single for Rooty, “Romeo” would be another top five US dance hit and to many is the definitive Basement Jaxx hit. — Andrew Cox


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79. The Flaming Lips – “Do You Realize??” (2002)

Taken from 2002’s masterful Yoshimi Battles the Pink Robots, “Do You Realize??” is a textbook example of a song’s tone brilliantly conflicting with its message. It sounds quite buoyant and bright, yet its sentiments (“Do you realize that everyone you know / Someday / Will die?”) are soberingly tragic and honest. Perhaps that’s what makes it exceptional, though, as it encompasses the album’s overarching theme of “facing” adulthood, conflict, and existentialism “when you’re not prepared to face them.” Wayne Coyne’s bittersweet boyishness has never been more arresting, and the rest of the band complement his truths with folky symphonic radiance. — Jordan Blum


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78. Amadou & Mariam – “Sabali” (2008)

Using a classic song at a moment of high emotion in a movie has always felt lazy — purely piggybacking off another artist’s hard work for your own narrative. I plea for a moratorium on the use of songs like “Heroes” or “Don’t Stop Me Now” for your scenes of revelry or heartbreak. Amadou & Mariam’s “Sabali” was recently used in a Coke ad, but my first response wasn’t “HOW DARE THEY?!?!” I was just enveloped by the song’s warm synths and breathtaking vocals from Mariam Doumbia. It’s like they knew it would specifically enrapture me like those personalized ads envisioned by Philip K. Dick. The trickery works every now and again. — Andrew Cox


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77. Avril Lavigne – “Complicated” (2002)

I’m sitting here hoping 18-year-old Avril Lavigne has figured out why he had to go and make it so complicated. Because that sucks that he did that. But instead of wallow in pity for Avril, I push past it to celebrate her, possibly even envy her. She, at the youngest of adult ages, was able to understand and preach the way of life: keep it simple, stupid. Lavigne is not about faking and you can tell by her unabashed smudged eyeliner and stick straight hair. She is known for speaking her mind and sticking to this expression of herself throughout her career. Her music is as music should be: raw; it is real emotion in word and sound. Perhaps that’s why “Complicated” is an undeniable classic, holding the number one spot on Adult Top 40 chart for 16 consecutive weeks right after its release and still being one of the first played songs during any of my angsty throwback jam sessions. — Sadie Burrows


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76. Girls Aloud – “Biology” (2005)

Following the Spice Girls’ short-lived world domination, UK girl groups grew exponentially in the early-’00s. Like many of them, Girls Aloud were created through a talent reality show, but they maintained longevity through twenty consecutive top ten hits across eleven years. Like the age of Motown, these groups were vehicles for pop producer auteurism, and the production team of Xenomania with Brian Higgins and Miranda Cooper were the Phil Spectors of this era. “Sound of the Underground” launched Girls Aloud and the Xenomania sound onto the world, but the true classic is “Biology,” which is an absolute adrenaline rush of pop perfection. The true chorus doesn’t come until two minutes in, but you don’t notice because it’s just all hooks. It’s the best example of why Girls Aloud are beloved overseas and not treated as just an old fad. — Andrew Cox


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75. The Shins – “New Slang” (2001)

For the first few years after The Shins’ debut LP, Oh, Inverted World, came out, its lead single, “New Slang” was everywhere (most famously in the film Garden State). It’s no wonder why, though, since its meek tale of disconnection, melancholia, and remembrance is a perfect example of early 2000s acoustic singer/songwriter self-pity  à la Elliot Smith and Sufjan Stevens. It’s very catchy, for one thing, and relatable, with James Mercer coming across as a lovable everyman whose pleas connect with anyone broaching adulthood uncertain, awkward, and eager for validation and belonging. It may have been overplayed, but it wasn’t overrated. — Jordan Blum


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74. Andrew W.K. – “Party Hard” (2001)

No matter what narrative you concoct for the story of ’00s music, Andrew W.K. will always be a square in a round peg. For all his connections to Detroit’s experimental rock scene (Aaron Dilloway, Wolf Eyes), W.K. was fully committed to this dude rock sound that appeared to be made by and for 15-year-olds. The frivolous simplicity can be misinterpreted as lazy songwriting that gives a middle finger to the sacred halls of artistic ventures. In the end, “Party Hard” is experimental itself — an attempt at finding how far dumb rock can go before we absolutely have to reject it. When the production and guitar riffs are that staggering though, a song like “Party Hard” shall always be praised. — Andrew Cox


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73. Lady Gaga – “Poker Face” (2008)

With the success of “Just Dance,” Stefani Germanotta, known to the masses as pop visionary Lady Gaga, had no choice but to up the ante with follow-up single “Poker Face.” The track is everything one would want in a pop song: chugging beats, futuristic synths, cleverly suggestive lyrics and a soaring chorus. The true highlight of the song is the juxtaposition in Gaga’s delivery, singing the verses in a processed, robotic style while letting her explosive passionate vocals loose in the chorus. Though it came out in 2008, “Poker Face” established Lady Gaga as a pop icon for future decades and pushed the mainstream further toward the world of sleek electronic music. — Drew Pearce


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72. The Postal Service – “Such Great Heights” (2003)

It’s justly the most beloved and best-known song from the duo’s lone album (2003’s Give Up). Sure, it could be reduced to being merely the electronic step sibling of Death Cab for Cutie (at least for the time, as Gibbard’s main project eventually went that route anyway); yet, he and partner Jimmy Tamborello also bring a newfound level of classy sparseness (namely, the tender piano motif) and positivity to it, which legitimizes its separate identity and makes clear why so many other artists—Ben Folds, Iron & Wine, and Amanda Palmer among them—chose to cover it over the years. — Jordan Blum


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71. Justin Timberlake – “Cry Me a River” (2002)

There was a ton of pressure on Justin Timberlake to release hits after he left his mega-popular boy band image behind and began his solo career. That was soon to pass as “Cry Me A River” quickly became that perfect hit. Utilizing Timberlake’s beatboxing skills, falsetto vocals and cut-throat breakup lyrics (supposedly about ex-girlfriend Britney Spears), the single became a hit, securing No. 1 on the Billboard Hot 100 chart and even winning a Grammy for Best Male Pop Vocal Performance. The track became a legendary breakup song, often heard at karaoke bars. — Nina Braca


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70. The Walkmen – “The Rat” (2004)

When I was fresh out of college, working 40-hour weeks in retail and spending my off-days in a state of dread, “The Rat” was pretty much all I wanted to listen to. I’m not sure if Hamilton Leithauser had that in mind when he wrote it, but the unbridled rage of “The Rat” is too relatable to be boxed-in for just the author’s use. Disgust is spewed out and ricochets back to him, as he knows he’s as much of a problem as the ex he’s lambasting. The snarl of the simultaneous verses and choruses is tampered by the self-flagellating bridge, highlighted by the all-too-relatable sentiment of “Now, I go out alone if I go out at all.” It’s an anthem for those who are getting older, but who aren’t sure how to mature. — Brody Kenny


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69. Bat for Lashes – “Daniel” (2009)

I discovered Bat for Lashes via the inclusion of “Moon and Moon” in Life is Strange: The Awesome Adventures of Captain Spirit. Comparable to Tori Amos’ “Winter” and Sufjan Stevens’ “John Wayne Gacy, Jr.,” it left me in awe. Thankfully, the rest of the Two Suns LP didn’t disappoint, with the record’s lead single, “Daniel,” also standing out. A glitzier, dreamier, and more vintage affair, it evokes the 1970s regretful romantism of Stevie Nicks and the mid-1980s pop brilliance of Kate Bush. Perfectly encapsulating Bat for Lashes’ punchily nuanced instrumentation and heartrending introspection, it remains one of her finest compositions. — Jordan Blum


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68. The Game (ft. 50 Cent) – “Hate It or Love It” (2005)

50 Cent’s greatness is often called into question — Get Rich or Die Tryin’ isn’t as great as its popularity and legacy suggest — but for one verse on “Hate It or Love It,” that all has to fade. 50 gives one of those verses you just have to know by heart with its efficient description of what growing up in American poverty is like. He alludes to Rakim in it and in this scenario, the comparison isn’t blasphemous. The legendary feature culminates in the classic chorus that could only properly be done in 50’s gunshot-slurred voice: “Hate it or love it, the underdog’s on top / And I’m gonna shine, homie, until my heart stops.” It makes sense that The Game would later feud with 50 Cent; he’s not even the main draw on the song he’s most known for. — Andrew Cox


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67. Amerie – “1 Thing” (2005)

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Amerie’s “1 Thing” is an early-’00s anthem for sure. The bombastic, go-go-sounding instrumentation backing Amerie’s unique soprano voice is hard to forget and easy to remember. The smash-hit is a single from her sophomore album Touch.

The song was written by both Amerie and D.C.-native Rich Harrison. Harrison produced the record “1 Thing” and like other go-go songs, the single features a funk sample (Meters’ 1970 funk recording “Oh, Calcutta!”).

Back on ‘05, there was no escaping this classic. If you remember, emcee-turned-successful-actress Eve hopped on the remix adding to the song’s critical success. “1 Thing” was also a prominent track on the romantic-comedy Hitch’s soundtrack and featured in the popular video game Saints Row II.

Digital and ringtone sales (remember that was a thing?) for “1 Thing” were certified gold by the RIAA; the song that’s arguably Amerie’s most popular topped the charts at number eight on Billboard’s Hot 100, becoming her first — and only — top ten hit. — Chanell Noise


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66. Kanye West – “Jesus Walks” (2004)

When I was 11 or 12, at my Catholic school’s after-school program, I remember one of the college students looking after us lending me his old-school brick of an iPod, and me walking around listening to “Jesus Walks” approximately five times in a row. Had I not have to give it back, I could’ve worn out the battery just playing that one song. Long before price-gouging pathetic Sunday Service brunches, “Closed on Sunday, you’re my Chick-fil-A” and other ways of making a turn of faith look like a reach for publicity, Kanye West spoke from the heart as a sinner trying to get right and not be mocked for it. Bucking more conventional wisdom of mainstream hip-hop success, he talked about God, and his record did get played. — Brody Kenny


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65. Kelis – “Milkshake” (2003)

Another amazing 2003 entry in this list is “Milkshake” by Kelis. The song was the lead single from her tertiary studio album, Tasty. The song was a dancier smash-hit that featured a memorable and catchy hook. Kelis repeats that her “milkshake brings all the boys to the yard,” over goblet-sounding drums mixed with electronic basslines.

A fun music industry trivia bit is that “Milkshake” was originally offered to Britney Spears for her fourth studio album, In The Zone. She passed on the Neptunes written-and-produced song which found its way onto Kelis’ radar. The match seems to be a best fit, considering that Kelis and the legendary producer-duo, The Neptunes, collaborated often.

“Milkshake” peaked at number three on the Billboard Top 100 back in December of ‘03. The song was nominated for a Grammy and landed a spot on the soundtrack for the 2004 comedy, Mean Girls.

Kelis’ popular single has appeared everywhere across the media and artistic landscape as it stands the test of time as an ode to confidence and sex appeal. Shows from Jane The Virgin to The Simpsons and Family Guy have interpolated “Milkshake” into their episodes. — Chanell Noise


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64. Sufjan Stevens – “Casimir Pulaski Day” (2005)

In breathy plosives, Sufjan Stevens delivers poignant vignettes about a first-love departed too soon. The death of this unnamed girl awakens a crisis of faith in the singer; the senseless nature of her demise is made all the more obvious when, on the same day, a cardinal collides fatally with a window. Nothing online can confirm whether this song is autobiography, but because of the emotion it evokes, it feels real. Maybe I want to believe him as a survivor of bone cancer myself, but Stevens is at his most honest here—a harbinger of the highs he’d reach mining his past on Carrie & Lowell. — Alex Wexelman


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63. Animal Collective – “My Girls” (2009)

Merriweather Post Pavilion is Animal Collective’s groundbreaking album, and “My Girls” is their groundbreaking song. It’s a song that’s ever-building, but never quite dropping – it’s a simple song with a simple message. Panda Bear’s layered vocals talk about how he only needs a couple of things in this life: a proper house, the ability to provide, and a soul, and isn’t caught up in fancy things or trendy things. The simple nature of the song alludes with the message the song sends – the bouncy synth melody, Panda Bear’s vocal repetition, and percussion scattered throughout. It’s a beautiful song that delivers a strong meaning. — Happy Haugen


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62. The Strokes – “Someday” (2001)

Similar to “Last Nite,” and frankly the rest of Is This It in general, “Someday” thrives off of its simplicity, which sort of makes ironic the lyric: “My ex says I’m lacking in depth / I will do my best.” There is a depth to it — if you want there to be — but the instruments and vocals offer the most in this track. The riff is instantly recognizable—symbolizing the signature Strokes nostalgia, and Casablancas’ delivery is earnest and engaged in his own memories. It predicts the passion and exhilaration to come on the following LP Room on Fire. — Danielle Chelosky


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61. Phoenix – “Lisztomania” (2009)

Paying homage to Hungarian composer Franz Liszt, French pop rockers Phoenix find a moment of rather chaotic writing in their music, mainly in the form of a fast-paced, racing piano line. Kicked up by Thomas Mars’ excited vocals, the track is full of quick, punchy lines, like “When it’s all over, we can barely discuss / For one minute only / Not with the fortunate only.” The song is an examination of crazed fans, akin to the frenzy around Liszt in the Romantic era of classical music. In the music video, the band is seen visiting the Franz-Liszt Museum in Bayreuth, Germany. — Virginia Croft


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60. Feist – “Mushaboom” (2004)

Named after a small village in Nova Scotia, Feist’s “Mushaboom” encapsulates the warm feeling of familiarity that comes with understanding all the tiny details of small town life. It’s a charming song of reflection and dreaming, as Leslie Feist allows herself to consider what she wants in life, even if she doesn’t want it to happen just yet. In a world that feels cramped and pushes for constant work, it’s nice to spend a few minutes just thinking “what if?” and “Mushaboom” accompanies this process with a sweet, playful pop melody. Feist’s warm vocals add a layer of calm and respite for those who need a song to let them float away. — Virginia Croft


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59. Gnarls Barkley – “Crazy” (2006)

CeeLo Green has done everything possible to ruin the allure of this song since it was named Rolling Stone‘s song of the decade (sexual battery case, homophobic tweets, the legitimately-terrible “Fuck You!”). It was better when everyone assumed he was some guy named Gnarls Barkley that existed just to offer the world one of the most effortlessly-cool songs of our lifetimes. The true story was a little more boring with Danger Mouse being the producer for Green. The Rorschach test-inspired video was also splendid, which calls back to a time when VH1 and MTV would introduce you to the next biggest hits just through music videos. Nowadays, a song like “Crazy” would need an accompanying TikTok dance to be heard by the masses. — Andrew Cox


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58. The Mountain Goats – “No Children” (2002)

There’s something strange about happily and proudly singing along with Mountain Goats lead singer as he shouts out the line “I hope you die! I hope we both die!” The lyrics are harsh and bleak, but when sung are often cathartic and freeing. “No Children” is an anthem to anyone going through a fucked up relationship and is the most enduring song off the 2002 album Tallahassee, which focuses on two characters on the brink of moving into a new house in Tallahassee, Florida. The song, and album as a whole, mark a change from previous TMG albums, as it was recorded in a studio with Peter Hughes playing the pseudo-role of a full backing band. It’s now a must at any Mountain Goats live show and a song that celebrates the feeling of darkness that anyone in a dysfunctional relationship has felt at some point or another. — Clay Sauertieg


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57. TV on the Radio – “Staring at the Sun” (2003)

TV on the Radio’s debut track “Staring at the Sun” is a strange song, you could say – it sounds like a constant buildup to a breakdown, but it never quite reaches that point. It’s fuzzy bassline along with the ominous “ooos” are so wicked sounding, and the chorus sounds like a march. There’s a lot of messages in this song – probably because it’s lyrics are based around a 13th century poem – but the best one that stands out is the line “note the trees because the/dirt is temporary.” The introspective lyrics coupled with the buildup of the song makes “Staring at the Sun” a song that leaves you wanting more. It makes you want to hear more of what TV on the Radio has in their discography. (Side note – watch a live performance of this song. It’s magical). — Happy Haugen


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56. Jay-Z – “IZZO (H.O.V.A.)” (2001)

Long before he was the billionaire business mogul you see today, Jay-Z’s lyrical wordplay earned him the moniker Jay-hova, because he was the self-proclaimed god of the rap industry. This eventually transformed into just Hova and then Hov ahead of the release of “IZZO (H.O.V.A.)” on The Blueprint in 2001, but the chart-topping song was nonetheless a massive hit. The lyrics tell of Hov’s upbringing and day of dealing drugs in the Marcy Projects and subsequent rise while sampling the Jackson 5’s “I Want You Back” in the background. Couple that with production from a budding star by the name of Kanye West and you have one of the most recognizable hits, and catchy choruses, of Jay’s storied discography. — Clay Sauertieg


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55. LCD Soundsystem – “Losing My Edge” (2002)

LCD Soundsystem’s popularity has done a good job of obfuscating how bafflingly weird and off-putting this debut single was. The beat and vocals sound like garbage; I have to imagine that professional studio producers loathe how “Losing My Edge” sounds. Also, James Murphy’s not even singing — it’s like an off-hand diatribe on how some DJs had the audacity to lower his ego. This song’s the epitome of that creative writing major that has no issue jotting down every synapse and presenting it as art, foregoing proper writing methods and editing because it’s “fake” or more accurately, he’s too lazy to do so. To some, it is pretentious drivel. Me? I love every second of it. — Andrew Cox


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54. Fugazi – “Cashout” (2001)

On “Cashout,” the second track on Fugazi’s last album, Ian Mackaye’s range shines through – from both a lyrical and musical standpoint. Throughout the song, you’ll find yourself hanging onto Mackaye’s every word as he tackles the issue of forced relocation by gentrification. The uneasy sound of the song keeps you on your toes, and the way the band seems to help create an anxious atmosphere keeps you nervous, up until an incredible breakdown with an unexpected string arrangement. Even though “Cashout” was released nearly 20 years go, it’s message still rings true to this day – “Everybody wants somewhere.” — Happy Haugen


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53. Justin Timberlake (ft. Timbaland) – “SexyBack” (2006)

In an era of mainstream music dominated by adult contemporary pop-rock, former *NSYNC heartthrob Justin Timberlake, with the help of legendary hip-hop producer Timbaland, was one of the many who sought to bring something fresh to top 40 radio. He accomplished this with “SexyBack,” a pulsing dance track made up of pounding bass, drum machine beats, infectious synth chords, brash lyrics and Timberlake’s alluring vocals. While the song primarily falls into the techno-pop genre, it still retains an R&B edge thanks to its electro-funk stylings. However, Timberlake opts to sing the song in the style of a rock n’ roll than that of R&B, not even bothering to use his signature falsetto. That very restraint, along with the tracks sweaty club sound and digitally distorted vocals, makes the brand of “sexy” that Timberlake is selling aloof and intriguing. — Drew Pearce


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52. The Streets – “Weak Become Heroes” (2002)

UK rave culture in the early-’90s didn’t decline through natural causes. British politicians targeted the scenes through fines of promoters who held them and through the Criminal Justice and Public Order Act of 1994. On the final verse of “Weak Become Heroes,” Mike Skinner shouts out classic ravers and then sticks his middle finger up to the government over the Criminal Justice bill. It gives a literal ode to the rave scene that had already been beautifully honored in its piano-loop production and a refrain in the chorus: “We all smile, we all sing.” — Andrew Cox


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51. Estelle (ft. Kanye West) – “American Boy” (2008)

Estelle was a newcomer in the US in 2008, before she dropped her second studio album Shine, with help from Kanye West, John Legend, and a number of other high-profile producers. “American Boy” became a giant hit, with its disco-inspired sound and Estelle’s smooth, sultry vocals, singing about riding the New York subway and fresh sneakers. The track eventually won a Grammy for Best Rap/Sung Collaboration. The track was inspired by John Legend suggesting she write a song about meeting an American man, but unfortunately, its effect on American men and their dating habits has yet to be proven. — Nina Braca