The 250 Greatest Songs of the 21st Century So Far

“Let love set you free to fly your pretty wings around,” sings Maxwell on “Pretty Wings.” The singer was a major neo-soul star at the turn of the century before going silent after his 2001 album, Now, and “Pretty Wings,” which anchored his comeback album BLACKsummers’night, was a reminder of the pleasures his highly unique balladry brings. “You need to cure and bring a connection through sound,” he said at the time. “Pretty Wings” skillfully blends heartache over a romance that falls apart with compassion toward a former lover, all while the music, co-produced by Maxwell and Hod David, builds to a horn-filled crescendo that feels like an epiphany. In 2010, it earned a Grammy Award for Best Male R&B Vocal Performance. —M.R.

Before peddling vaccine misinformation became her main output, Mathangi Arulpragasam was one of pop’s most exciting and provocative visionaries. With 2008’s “Paper Planes,” she and producer Diplo flipped a killer sample of the Clash’s “Straight to Hell” for a thumping, gun-blasting schoolyard chant that sure sounded like an audacious boast of violence. At heart, it was candy-coated satire about the indignities of the immigrant experience, where newcomers to the U.S. were often greeted with mistrust and paranoia — things M.I.A. had experienced while trying to secure a work visa to visit from England. For a time, anyway, no one on the corner had swagger like this. —J.F.

Maybe this is the Millennial National Anthem. Lil Uzi Vert’s “XO TOUR Llif3,” a quintessential artifact of the SoundCloud era, longs for a future deferred. “All my friends are dead,” Uzi raps, almost too jovially given the fact that the line is preceded by “push me to the edge.” The song is about Uzi’s breakup, but it perfectly captures the mood of its time, and Uzi’s broken-hearted anthem cut through to a deeper sense of loss that seemed to engulf a generation. In the emo rap era that Uzi perfectly encapsulates on “XO TOUR Llif3,” we see growing beyond its traditional borders into unseen terrain. Who better to chart that course than Lil Uzi Vert?–J.I.

Countless songs have been written about heartbreak, but few songs ache the particular way Amy Winehouse’s title track from her 2006 retro-soul masterpiece, Back to Black, does. “We only said goodbye in words/I died a hundred times/You go back to her/And I go back to black,” she sings. Fueled by grief and loneliness during a break in her toxic, volatile relationship with Blake Fielder-Civil, “Back to Black” projects both a wounded fragility and an almost-snarling howl of anger. While “Rehab” may have been the album’s catchy pop single, it’s the richness of this one that makes it stand the test of time. —L.T.

In an industry of manufactured outlaws, Kacey Musgraves gave country music one of its most rebellious anthems with this breezy 2013 singalong. The sleeper centerpiece of her debut album, Same Trailer Different Park, “Follow Your Arrow” cast a knowing look at the judgmental hypocrisy of small-town life and its gossip. “If you can’t lose the weight, you’re just fat/But if you lose too much, then you’re on crack,” she sang over simple acoustic guitar. But the payoff — and the most pearl-clutching — lines came in the song’s chorus, when Musgraves implored her listeners to kiss boys or “lots of girls, if that’s something you’re into” and roll up a fat one. It was the sound of an artist truly cutting her own path. —J.H.

An apotheosis moment for Atlanta trap pop, “Bad and Boujee” had it all: a viral meme (“rain drop, drop top”), a crawling beat from era-defining producer Metro Boomin, a guest verse from Lil Uzi Vert before his “XO Tour Llif3” blowup, and, of course, Migos, the high-octane trio reshaping hip-hop in their mold of trap houses and triplet flows. The song was a smash on Soundcloud and Spotify, and at strip clubs, ultimately growing to be the type of pop hit that knocks Ed Sheeran out of the top spot. The group’s Takeoff compared their star-making moment to Christmas Eve: “You just know that everything you asked for is going to be there up under that Christmas tree,” he told The New York Times. “It’s our time now.” —C.W.

There are many versions of Drake and songs that exemplify them. “Hold On, We’re Going Home” is one of Drake’s most earnest pop-star moments ever. Alongside Majid Jordan, he crafted a dreamy ode to unfettered romance that’s still being co-opted and karaoke’d to this day. When he gently calls his romantic interest “home,” lovers hope home feels like Jordan, 40, and Nineteen85’s Eighties-inspired production. The song is a snapshot of Drake the certified lover boy, who’s gentle enough to have someone “act so different around me,” but talented enough to croon it unforgettably. When he rhymed, “I still got some love deep inside of me” on 2023’s “Rich Baby Daddy,” he was referring to whatever well he culled for this wedding song favorite. —A. Gee

Jepsen’s 2011 mega-blockbuster helped initiate the era of pop music engineered to cater to TikTok dance trends and social media-driven pop virality that we’ve been living in for the past dozen years. But Jepsen’s sugar-rush hit and modern-day wedding-reception standard almost never existed in the form we know it: “I thought that what I was singing at the time — ’Hey, I just met you, and this is crazy’ — was just, like, filler lyrics,” Jepsen said in 2017, explaining that the song’s chorus was initially written as a pre-chorus. When Jepsen’s collaborator Tavish Crowe suggested they make it the chorus, he just might’ve changed the world. —J. Bernstein

The Weeknd’s foray from dark R&B to 1980s-inspired pop anthems complete with shiny synths and retrowave drums didn’t just pay off — it notched him the most-streamed song on Spotify of all time. With more than 5 billion listens on the streaming platforms, “Blinding Lights” is one of a few songs the Weeknd and Swedish producer Max Martin teamed up on for the 2020 commercial juggernaut After Hours. The song’s lyrics sound buoyant with a hint of a dark undertone as the protagonist chases the object of his desires. “Blinding Lights” is like a song you’ve heard a million times, and might not mind hearing a million more. —Waiss Aramesh

In the fall of 2018, Ariana Grande celebrated the end of her time as a tabloid sensation by reclaiming her narrative. Written in the wake of a year where her romantic relationships with the innovative MC Mac Miller and the SNL youth rep Pete Davidson lit up social and traditional media, “Thank U, Next” is sonically gossamer yet lyrically muscular. Despite the insouciant title, “Thank U” isn’t a gripe; over glossy synths, Ari trills her feelings of gratitude toward her former paramours. Eventually, she reveals that she’d found “someone else” with whom she’d been “havin’ better discussions.” That person? Turns out “her name is Ari” — because like her hero Whitney once sang, the greatest love of all is learning to love oneself. —M.J.   

“That was one of those songs where I remember telling [my manager], ‘I don’t know how to write about someone else’s life,’” said Eminem, on writing the inspirational narrative of his 8 Mile character, Jimmy “B-Rabbit” Smith. “It would sound so corny if I was just rapping as Jimmy Smith Jr. How is that going to come from a real place?” Naturally, Em pulled from his own experiences as a struggling battle rapper balancing his ambitions with baby-mama drama, financial struggles, and trailer-park malaise — by the third verse of “Lose Yourself” the “he” stealthily turns into “I.” The result was hip-hop’s very own “Eye of the Tiger,” a motivational speech performed with acrobatically cunning rhymes. The gambit earned him 12 weeks atop the Hot 100, and the first Best Original Song Oscar given to a rapper. —C.W.

“Drivers License” was destined to be an instant hit. Olivia Rodrigo spent months teasing the song, the anticipation sparkling with speculation over the alleged real-life love triangle that may have inspired it. But the way “Drivers License” actually arrived makes “instant hit” feel insufficient. The song carries the kind of melodic, lyrical, and vocal power that speaks directly to teen angst, and makes everyone over 20 feel 16 again. It not only made Rodrigo an overnight pop star, it also was so good it left little doubt that Rodrigo’s musical journey would not be that of some post-Disney flash-in-the-pan. Rarely does an artist — let alone one who’s just 17 — drop a single that feels like it could define a year, a career, and an era. —J. Blistein

A moment of stark vulnerability that became a signature song for one of the century’s biggest pop acts, “Spring Day” turned personal grief into a surging, triumphal power ballad. “I wish to end this winter/How much longings must fall like snow/Before that spring day arrives,” goes the English translation of RM’s passionate lyrics. The song is associated with a tragedy in the band’s native Korea — the sinking of the ferry MV Sewol in 2014, in which 304 people died — but its sense of resilience and hope wrought from loss has a transcendent feel, soon to be mirrored in the band’s global takeover. BTS would have bigger crossover hits around the world, but few songs approach the gathering power of their music like this one. —J.D.

The lead single from Asian American indie singer-songwriter Mitski’s breakout album Puberty 2 is about fumbling toward the acceptance of your own embattled identity. Despite its achingly intimate subject matter and soft start, the song becomes an inferno of anger, confusion, and loss. “Your mother wouldn’t approve/Of how my mother raised me,” Mitski sings against swells of distortion. Dropping at a time when what it meant to be an American was becoming an increasingly contested issue, the song felt like a rallying cry for anyone who didn’t fit into the ticky-tacky mold of what constitutes all-American-ness. —B.E.

LCD Soundsystem blasted onto the New York rock scene of the early 2000s with an armload of dance-rock beats and no small amount of irony. But by 2007, LCD frontman James Murphy was 37 and had seen a lot, and on “All My Friends,” he cooked up an unconventional, oddly beautiful anthem about aging. Over a hammering piano ostinato and gentle disco-rock pulse, Murphy ruminates on life choices, long nights, and kids who seem “impossibly tanned,” tossing in a Pink Floyd reference and a dollop of regret. But as the song stretches out to more than seven minutes, that piano riff starts to feel like a life force, and Murphy calls out for his friends with soulful sincerity. —C.H.

The steady, pulsating thud that backs the entirety of Lorde’s devastating deep cut “Ribs” is the heart of the song. It’s the sound of an intensely perceptive 16-year-old pounding on the door to the past that slammed shut behind her. “I’ve never felt more alone/It feels so scary, getting old,” she repeats, growing more frantic with each lyric. But she was never truly alone. An entire generation adjusting to their twisted coming-of-age experience felt every word with crushing resonance. They still do. The electropop track races between comfort and chaos, haunted by nostalgia for the past, present, and future. Lorde’s prophecy is pierced with a spine-tingling realization: “That will never be enough.” For just a few minutes, it is. —L.P.

Lana Del Rey makes the running time of her longest track to date — all nine and a half minutes — entirely worth it. What starts as a sun-soaked California love letter becomes a psychedelic-rock trip filled with fuzzy guitars and woozy bass. It’s a last-gasp-of-summer dream that fully embodies the killer lyric “fresh out of fucks forever.” Del Rey released the track as the second single off her career-defining LP Norman Fucking Rockwell, over the protestations of her managers, who were hoping for a standard three-minute pop song. But that’s not the vibe Del Rey was after. “End of summer, some people just wanna drive around for 10 minutes and get lost in electric guitar,” she told Zane Lowe at the time. —M.G.

Beyoncé stopped the world yet again when “Formation” crash-landed like a spaceship in 2016, ushering in her era as a political voice, a once-in-a-lifetime touring artist, and a true troublemaker with her Super Bowl 50 performance of the song, dripping Black Panther aesthetics. Yet, beyond all that historic cultural context, “Formation” remains one of Beyoncé’s most interesting sounding songs to date. Armed with production from MikeWillMadeIt that was somehow at once kookily mechanical and royally orchestral and vocal contributions from his rambunctious Rae Sremmurd protege Swae Lee, and New Orleans bounce queen Big Freedia’s blessings, Beyoncé solidified her rap bona fides on “Formation,” letting herself become the most crass and defiant she’d ever been to that point. —M.C.

Songwriters Max Martin and Dr. Luke had been listening to early-aughts alt-rock like Yeah Yeah Yeahs when Martin settled on a hypothetical: What if a song like that had a soaring chorus? The result was Kelly Clarkson’s “Since U Been Gone,” a song that quickly became both an enormous hit and (perhaps because of the sound it was aping) a universal critics’ darling. From the very first line, Clarkson makes the song her own; she later recounted having to argue with her collaborators about her desire to jump an octave for the chorus. But even if the song represented, for Clarkson, a fraught experience with A-list songwriters, it remains a masterful slice of early-aughts indie-pop cross contamination. —J.Bernstein

Co-written and produced with Jermaine Dupri and Bryan-Michael Cox, the smooth pseudo-ballad is found on Usher’s 2004 magnum opus LP of the same name. In it, the R&B icon admits to getting a woman he “barely even know[s]” pregnant, revealing other indiscretions in what feels more like raw testimony than a classic confession. Known for its themes of guilt, secrecy, and consequence, the emotional weight and vulnerability sparked widespread speculation about whether the track was autobiographical, especially given Usher’s high-profile breakup with Chilli of TLC fame. “It wasn’t a specific situation that happened in my life right now,” he clarified in an interview, adding that its content is about something he, and others, could deeply relate to. —J.J.

Bun B and Pimp C had been releasing albums for 15 years when they teamed up with OutKast and Three 6 Mafia, flipped a Willie Hutch track, and recorded the biggest and most impactful song of their career. Few artists have the audacity and talent to open with a beatless verse for more than a minute like André 3000 (a decision that initially enraged Pimp C). Yet as the song unfolds, UGK craft an endearing ode to love and commitment that comes off earnest without a hint of maudlin weepiness. Nearly 20 years later, there’s a reason why the Grammy-nominated track is heard at both clubs and weddings. —J.N.

Thomas Bangalter and Guy-Manuel de Homem-Christo kicked off our new century with “One More Time,” taking the elastic house music they’d perfected on their 1997 classic, Homework, into a whole new stratosphere of ecstasy. Teaming up with singer Romanthony, they Auto-Tuned his performance to give the song a winking retro feel that actually ended up forecasting what a lot of pop vocals would start sounding like in the years to come. “One More Time” was the lead single off Daft Punk’s brilliant album Discovery, which mixed dance music with Seventies and Eighties rock and pop flavors to create a classic dance-music LP — and it became a bona fide hit single, too. —J.D.

“I got lucky in different ways,” Calvin Harris said of the decisions that led him to his glorious global Number One with Rihanna. “I wrote the right songs at the right time, I picked the right genre of music, I started DJ’ing in the U.S. at the right time. If I hadn’t made all of these reckless decisions, I wouldn’t have been put in that place.” That new focus on DJ’ing led to a tour with Rihanna, which led to “We Found Love,” whose circus-like organ, soaring hook, and broadly but keenly utilized filter sweeps (e.g., the instruments going underwater at the top of verse two) bridged pop and EDM more adroitly than just about any other record of its time. —M.M.

The debut single by the Killers replicates how a whirlwind of emotions can overwhelm you: the fusillade of post-punk-inspired rhythm, Brandon Flowers’ insistent and anguished chanting, and his deep shame over a night that turns sour when a girl he kissed eventually hooks up with someone else. His vocals, inspired by Iggy Pop’s delivery on “Sweet Sixteen,” encompasses the uncontrollable passion of experiencing a life moment all at once. “Mr. Brightside” sounds like a lightning bolt, a quality that not only helped it turn into a defining track for rock’s early-aughts “dance-punk” era, but also the type of anthem every Gen Z festivalgoer will know by heart. —M.R.

Rick Rubin moved away from hip-hop in the Nineties to work with rock acts like Red Hot Chili Peppers, Tom Petty, and Slayer. But he returned to his roots in 2003 for Jay-Z’s “99 Problems.” It’s a work of genius that fuses the chorus of Ice-T’s “99 Problems” with the drum beat from Billy Squier’s “The Big Beat,” elements of Mountain’s “Long Red,” and Wilson Pickett’s “Get Me Back on Time.” In the lyrics, Jay calls out music critics, racist police officers bringing drug-sniffing dogs to his car, and pathetic men unworthy of his time. (Each verse is about a different “bitch,” and it’s never a woman.) The song wraps with Jay calling out Rubin by name. “He pushed me to take the track to a whole other level.” Jay later said.—A. Greene

D’Angelo may have ended up with mixed feelings about the pelvis-teasing video for this single, but there’s no denying that the super-slinky “Untitled” is rivaled only by “Let’s Get It On” for the greatest-bedroom-jam-ever title. As with most of Voodoo, the formidable rhythm section of Pino Palladino and Questlove are so far behind the beat that the track practically time travels, while D’Angelo’s ever-cresting lead vocals and harmony stacks offer — in classic soul tradition — a libidinal take on gospel. The song casts such a distinct spell that it seems downright wrong to listen to it with the lights on. —B.H.

When Chappell Roan released “Pink Pony Club” in 2020, she had just been signed to her first label contract as a sad-girl singer-songwriter, but as she grew up, she wanted to make songs that were bigger, bolder, and more celebratory. The song captures that liberation, spinning a tale of a girl moving from Tennessee to West Hollywood to become a go-go dancer. The track got some moderate buzz upon release, but it took off four years later, riding the wave of Roan’s breakthrough debut album, The Rise and Fall of a Midwest Princess. She finally got to sing it at the Grammys in 2025. By then, “Pink Pony Club” was bigger than a hit: It’s the pop anthem that best defines her joyful arrival as one of the most compelling pop voices of her generation. —B.S.

“Essence” is bewitching, shimmering, and impossibly soulful. Of course, this Tems-fueled 2020 single is about being reluctant, yet its tropical bass and mashup of sharp and cool tones make it feel wonderfully direct and decidedly urgent. No shocker that “Essence” became the first song by a Nigerian artist to bogart Billboard’s Hot 100: Its chorus is so indestructible, Tin Pan Alley’s best songwriters are low-key hating from the grave. Tems’ humid whine — modal, plaintive, and electric— bristles with untapped desire as she insists, “You don’t need no other body.” And Wizkid’s mellifluous effusions serenade your ears, while inviting you to a scorching-hot dance floor. “Essence” essentially intoxicates. —W.D.

Lady Gaga would burn the City of Love to the ground if it meant her insatiable craving for affection both dangerous and delectable would be satisfied. “Je veux ton amour et je veux ta revanche,” she sings with pure pop seduction on “Bad Romance,” filtering her pleading confession “I want your love and I want your revenge” through a more romantic language. The Fame Monster single is relentless and captivating. Gaga performs with expansive range as her distinct tone waltzes with skittering and eruptive production, the thudding techno kicks matching the pulse of a lovelorn heartbeat. The passion of the singer’s Parisian love affair mirrored the utter devotion that permeated and defined her pop breakthrough. Her willingness to go to fanatical extremes made her undeniable. —L.P.

The second single from his sophomore album, Gemini Rights, Steve Lacy’s “Bad Habit” has the secret sauce of a world-spanning hit record. Those buoyant drums clomping beneath equally rambunctious guitar riffs helped reconfigure the modern pop landscape. The song arrived just as Covid-19 restrictions began easing, ushering us out of our post-2020 malaise with the perfect pop banger about unrequited or, rather, unexplored love. Who among us hasn’t realized too late that the feeling was indeed mutual? “Bad Habit” would be nominated for Song of the Year, Record of the Year, and Best Pop Solo Performance at the 2023 Grammys, along with Gemini Rights, for which Lacy won Best Progressive R&B Album. —J.I.

By the time Adele released her second album, 21, pop hits often sounded as gloriously oversized as Jumbotron screens at concerts. But leave it to our greatest modern cabaret singer to remind us that simplicity works too. Written (with Semisonic’s Dan Wilson) in the wake of a gutting breakup, “Someone Like You” offers up little more than a voice, a piano, and heartbreak. But it isn’t merely another churned-out, one-that-got-away ballad; it’s a deeply personal song that still manages to be universal. Adele’s genius as a singer emerges each time she hits “’Don’t forget me,’ I begged” in the choruses. Without oversinging, she manages to sound more desperate each time she arrives back at that line. Even if AI robots take over the planet, it’s easy to imagine one of them relating to this song. —D.B.

Billie Eilish rose out of the all-American teenage wasteland to blow up into everybody’s favorite pop nightmare. With “Bad Guy,” she gave her generation a new misfit anthem, hitting Number One three years after she became a SoundCloud cult figure. It’s the sound of a home-schooled 17-year-old weirdo turning her diaries into macabre bedroom electro-goth pop, giving an evil cackle when she sneers, “I’m the bad guy — duuuuh!” Billie and her brother-producer-wingman Finneas made everyone else sound tame with “Bad Guy,” making a blockbuster hit out of her debut, When We All Fall Asleep, Where Do We Go? But it introduced the world to a voice that would continue to define pop’s cutting edge for years to come. Duuuuh. —R.S.

There’s a reason young people have taken to idolizing mid-2010s hip-hop. The era saw an abundance of releases that went on to define a generation. At the center of it all was a red-hot Drake, at the zenith of his cultural influence, atop a peak seen only by the likes of Beyoncé, Taylor Swift, and, as he’s apt to remind us, Michael Jackson. In particular, Drizzy was at his most powerful in 2015. He successfully warded off threats to his legitimacy in his beef with Meek Mill and capped off the affair by dropping a cross-genre hit. “Hotline Bling” would turn out to be a viable microcosm for Drake’s career, an undeniable pop crossover capable of reorienting the conversation around him. If he could only rediscover the formula today. —J.I.

Mariah Carey bounced back from her rough early-2000s with a new attitude; on this weepy slow jam, she didn’t go for the big notes she was known for right away, instead laying down lightning-fast, stream-of-consciousness lyrics over a sparse, piano-led background, letting the tension and longing inside build until they have to explode skyward. “We Belong Together” derives its majesty from the way it balances its musical tension with Carey keenly describing moments of uneasy solitude: feeling bereft over “sitting here beside myself,” sighing over hearing Bobby Womack and Babyface on the radio. In a way, that precisely expressed knowledge of music’s power doubled as a predictor that “We Belong Together” would eventually land in the upper echelon of heartbroken hits. —M.J.  

For this turn-of-the-century classic, OutKast jacked up the tempo to 155 beats per minute and tossed in fiery guitar, frantically tongue-twisting lyrics, and even a damn gospel choir. It shouldn’t have all worked together, and yet it sounds fucking awesome. The ominous “Bombs over Baghdad” chorus took on a strange resonance when the U.S. invaded Iraq a few years later, even though the lyric was actually a metaphor about half-assed music being made around the turn of the century. Nothing half-assed here — “B.O.B.” sounded like little else in hip-hop at the time, and that’s just as true today. —C.H. 

Daddy Yankee unleashed a reggaeton hailstorm with a tune that was unlike any previous “Latin explosion”-style record: This was no polite, conga-laced ditty about unrequited love. Like so many classic anthems that emerged from the underground, “Gasolina” was all about being young and partying until your body gives out. Daddy’s vocal line was fast and furious, but it was also the production by Luny Tunes that made history with that plunky, cartoonish minor-key synth line that sounds like a mashup of a Clavinet and an African mbira. There’s also the uncredited voice of Glory, proving on the call-and-response chorus that desire is a two-way street. No wonder “Gasolina” became a global milestone. Two decades on, it still leaps out of the speakers like an overcaffeinated beast. —E.L.

SZA has said she hates being generalized as an R&B singer, which makes sense since her music is an incisive blend of rock, rap, pop, and more. But she did make a perfect R&B song with “Snooze,” her longest charting hit to date. It helps that she had R&B impresario Kenneth “Babyface” Edmonds and guitar hero Leon Thomas backing her with a classic instrumental that sounds like longing incarnate, but SZA loaded it with her irreverent wit and signature contradictions to make it utterly unforgettable. People like to compliment records as timeless, but this one shines precisely because it boasts such a contemporary take on the age-old drama of a relationship going wrong — matched with a feeling so right. —M.C.

The hype surrounding New York garage-rock revivalists the Strokes was deafening even before they released their first single — and the punchy “Last Nite” delivered on that hoopla with the reflexive cool of a Lower East Side lifer. (The giddy guitar solo from pop scion Albert Hammond Jr. helped, too.) Sure, the notion that it was a scruffy homage to Tom Petty’s “American Girl” made the Florida rocker “laugh out loud,” he told Rolling Stone in 2006. But the way it placed frontman Julian Casablancas’ sandpaper yelp amid squalling guitars and a running-away-from-itself beat made “Last Nite” one of the most compelling pieces of evidence for the case that, at least musically, there was a clear winner in rock’s turn-of-the-millennium splintering into post-punk cool and post-grunge angst. —M.J. 

In 2020, Bad Bunny proved he was an unstoppable force with the release of his second studio album, Yo Hago Lo Que Me da La Gana. But with its standout track “Safaera,” the Puerto Rican musician went even further, cementing himself as the ultimate innovator of Latin music. On the surface, the song is a sticky Caribbean bash about twerking and all-out hedonism, but each dembow blow hits harder, deepening the track’s historical impact. Here, blunt in hand, Bad Bunny ushers in the new, party-hungry musical generation with an artistic feat that spins through decades of references, including a well-timed sample of Missy Elliott’s “Get Ur Freak On,” 10 different rap flows, and bombastic bars from reggaeton legends like Ñengo Flow and Jowell and Randy. —M.G.

It can be easy to forget how shocking it was in 2012 to press play on Channel Orange and, after a short intro, crash into this instant-classic love song. Most people at the time knew Frank Ocean as the most melodic member of the fast-rising Odd Future crew; some might have heard about his experience writing for Beyoncé and Justin Bieber, or tuned into the sample-jacking, genre-surfing buzz around his 2011 mixtape Nostalgia, Ultra. But no one was ready for what he did on “Thinkin Bout You,” cooing sweet romantic metaphors on the verse before unleashing his generationally smooth falsetto on the hook: “Or do you not think so far ahead?/’Cause I been thinkin’ ’bout forever.…” A simple melody, delivered unforgettably — sometimes that’s all it takes. By the time the song was done, Ocean was firmly established at the forefront of both R&B and pop. And while he’s often seemed uninterested in new music in recent years, this song is brilliant enough to keep him in the canon forever, just like he said. —S.V.L. 

All hail the pop queen: It’s Britney, bitch. Britney Jean Spears was the teen-spirit supernova of the Y2K era, the country girl who blew out of Kenwood, Louisiana, to lead a youth explosion on MTV’s Total Request Live. The experts predicted she would fizzle out fast, but she’s spent her career proving them wrong. “Toxic” is the ultimate Britney classic — she never sounded so brash, so confident, so herself. Swedish producers Bloodshy and Avant build her a sonic glam-disco fun house, all spy-movie strings and surf-guitar twang, while she sings in her sly drawl about slipping under an erotic spell. “It’s basically about a girl addicted to a guy,” Britney told MTV. “This villain girl, she’ll do anything to get what she wants.” But when she sings “a taste of a poison paradise,” she could be describing this song. “Toxic” became her signature hit, the one that sums up her legacy as one of pop history’s all-time-great hitmakers. She’s dangerous — and she’s loving it. —R.S.

After they found massive success with their 1997 breakthrough album, OK Computer, Radiohead could have repeated the formula. Instead, they went as far away from conventional rock as they possibly could — to the bunker, to the ice age, to the land of glitchy electronica — for their masterpiece, Kid A. Its peak is “Idioteque,” the propulsive, magnetizing centerpiece about global warming and the fall of society (casual stuff). Guitarist-mastermind Jonny Greenwood cooked up 50 minutes of synth improvisation, and Thom Yorke took just 40 seconds of it, including a stellar sample of Paul Lansky’s 1976 composition “Mild und Leise” that Greenwood discovered off a compilation. “The others didn’t know what to contribute,” Yorke later said. “When you’re working with a synthesizer, it’s like there’s no connection. You’re not in a room with other people. I made everyone’s life almost impossible.” But it was worth it: “Idioteque” became a live staple for the band, and remains a defining moment in its career. Impending doom never sounded so cool. —A.M.

The major rap figures of the Nineties and 2000s had been imperiously cool hustlers like the Notorious B.I.G. and Jay-Z, for the most part. Kendrick Lamar became a superstar of the 2010s by leaving every emission, contradiction, and conflicting personal impulse all the way out there. His 2015 album, To Pimp a Butterfly, was a sweeping, jazz-steeped self-interrogation, and its Pharrell-produced centerpiece anthem, “Alright,” reached out for connection and community in a moment of darkness. Fittingly, its call-to-action refrain, “We gon’ be all right,” became a slogan at Black Lives Matter protests the nation over — making the song itself a new-look “We Shall Overcome” for an urgent new wave of activism. “You might not have heard it on the radio all day,” Lamar said in an interview, “but you’re seeing it in the streets, you’re seeing it on the news, and you’re seeing it in communities, and people felt it.” —J.D.

Swedish singer Robyn had been making records since the 1990s, but she touched an enormous nerve with “Dancing on My Own,” a sparkling ode to the feeling of carving out your own little world in a corner of the club. Working with fellow Swede writer-producer Patrik Berger, the singer combined isolation and sadness that was tinged with resilience, a sense of using the track’s swirling synths and pulsing groove as a means to push through the romantic betrayal and emotional chaos she sang about in the song’s strikingly unguarded lyrics. “Dancing on My Own” became a pop-culture totem (deployed by Lena Dunham in a pivotal scene in the HBO show Girls), an LGBTQ+ anthem (“Because we get to dance our pain away,” said Sam Smith), and a blueprint for pop artists looking to turn their real experiences and feelings into the stuff of universal pop catharsis. Robyn superfan Lorde summed it up in one word: “Perfect.” —J.D.

Taylor Swift’s toughest, rawest, most passionate heartbreak anthem. “All Too Well” began as a five-minute steamroller on Red, a pained love story summed up by the lost scarf her ex still keeps in his drawer, after she left it at his sister’s house. It became a fan favorite, but never a hit or even a single. For years, she wouldn’t even sing it. “It was about something very personal to me,” Swift said. “It was very hard to perform it live.” She thought she’d finished telling this story. But nearly a decade later, she reworked it for Red (Taylor’s Version), digging up the lost verses from her original 10-minute draft — tearing up her own masterpiece to create something new. “All Too Well (10 Minute Version)” became a massive phenomenon, the longest Number One hit in history. (It broke the record set by “American Pie.”) On her Eras Tour, it made stadiums around the world scream “Fuck the patriarchy!” on cue every night. If you’re picking one song to capture the genius of Swift, you can’t top “All Too Well” — whichever version you choose, it’s a classic. —R.S.

Just when we thought the big, overpowering rock riff was a thing of classic-rock past, Jack White resplendently brought it back from the dead. Famously conceived during a soundcheck during a White Stripes show, “Seven Nation Army” returned raw simplicity and mystery to rock & roll. The title was a reference to the way White would mistakenly refer to the Salvation Army when he was a kid, and the spew of imagery in the lyrics alluded to the scrutiny White and his musical and one-time personal partner Meg were suddenly receiving. “At the time I took some inspiration about some people I knew gossiping,” White said later. But there was nothing cryptic about the power of that riff (played on guitar but sounding like a bass), the tension it builds before the track explodes, White’s elf-in-heat delivery, and a lead guitar that recalled Clapton’s Cream era. As an added bonus, White gave college and high school marching bands the repertoire upgrade they all desperately needed after years of playing Chicago hits. —D.B.

From the moment those opening horns explode open the track, it’s clear that “Crazy in Love” is more than just a single: It was a warning to the rest of the pop world that Beyoncé the solo star had officially arrived. Like much of the artist’s work, the song bridges the relationship between the past and the present, with Beyoncé delivering a modernly funky R&B cut. Rich Harrison produced the track, which led off the rollout of the star’s first solo album, Dangerously in Love, and perfectly placed a Chi-Lites sample that gives the track enough of a retro touch to feel like an instant classic. Beyoncé herself sounds effortless: A natural, convincing confidence made her stand out while in Destiny’s Child, and carries the buoyant, catchy anthem. Paired with an instantly memorable verse from Jay-Z, “Crazy in Love” was destined for greatness from the jump, influencing a generation of pop stars in its wake. —B.S.

Though New York art-punk trio Yeah Yeah Yeahs are often celebrated for their off-the-wall energy, it’s a quieter moment that became the band’s most-enduring song. There’s a specific beauty to the stark, bare-naked humanity of Karen O’s performance over Nick Zinner’s quavering guitar: Though Karen often feels like a living firework blazing through the Yeah Yeah Yeah’s most explosive eruptions, she’s suddenly disarmed and unguarded on “Maps,” wielding nothing but a tremble in her voice and the sheer honesty of a heartfelt message. The lore is that the song was about her then-boyfriend Angus Andrew of the band Liars — the title is rumored to be an acronym for “My Angus Please Stay,” a detail that a tear-stained music video seems to confirm — but the real story is almost secondary. What remains in “Maps” is pure feeling, so much so that the song has reappeared as musical inspiration for artists from Kelly Clarkson to Beyoncé over the years. Still, the original has held out strongest through the decades, speaking to anyone who has understood whispered pleas in the face of cruel timing and inevitable goodbyes — and what it means to hold on even when it hurts. —J.L.

Missy Elliott dropped “Get Ur Freak On” just in time to rule the radio in the long, hot summer of 2001 — and nothing was ever the same. It was more than just the latest mind-bending Missy smash — it was a challenge, a dare, the sound of Miss E and Timbaland defying everyone else to keep up with the future or get left behind. The dynamic duo from Portsmouth, Virginia, were music’s most radically innovative team, ever since they flipped hip-hop upside down with their 1997 debut hit, “The Rain (Supa Dupa Fly).”But “Get Ur Freak On” was one step beyond, riding a crazed space-bhangra beat. Timbaland warps a tabla hook into head-spinning Dirty South avant-funk, playing the six-note motif on the tumbi, a one-string Punjabi guitar, while the party people go off in Japanese and Hindi. Missy yells her epic “Hollaaaaa!,” commands all freaks to the dance floor, hocks a loogie, and boasts, “I know you dig the way I sw-sw-switch my style!” It was a nonstop freak manifesto that made the musical future sound limitless. And after more than two decades, “Get Ur Freak On” still sounds like the future — everything vibrant and inventive and cool about 21st-century pop is in here somewhere. Holla, forever. —R.S.