The 250 Greatest Songs of the 21st Century So Far

So much of FKA Twigs’ crushingly beautiful album Magdalene is rooted in pain: The track list is an unblinking look at shattering heartbreak, appalling racism, bone-deep loneliness, and even the physical aches of a surgery she had to remove several fibroids from her uterus. But no song captures her agony like “Cellophane,” a celestial ballad that builds higher and higher, balancing precariously and constantly threatening to topple over. The breaking point seems inevitable as Twigs asks, voice wavering, “Why didn’t I do it for you?” The question is so raw, it almost hurts to hear her ask it, but part of Twigs’ power is being so fearless in the face of vulnerability. —J.L.

At a 2012 press conference, Leonard Cohen told the assembled reporters: “I’ve come to the conclusion, reluctantly, that I am going to die. So naturally those questions arise and are addressed. But, you know, I like to do it with a beat.” Four years later, just two weeks ahead of his death, the title track of his final living album did just that — it’s a conversation between a dying man and an impassive God, low-key but spine-tingling: “If you are the dealer, I’m out of the game … I’m ready, my lord.” And while the beat on this one is subdued — the hymnal organ is at the arrangement’s center — the twisty little bass line gives this astounding envoi a welcome groove. —M.M.

In 2005, Three 6 Mafia released Most Known Unknown, a title reflective of their odd position of being underrated by fans despite thriving as an immensely influential gold-and-platinum act that virtually invented crunk music. Ironically, the album augured its biggest successes to date, with “Stay Fly” as the anchor. Produced by Mafia linchpins DJ Paul and Juicy J, it’s an all-Memphis showcase threaded around a sped-up sample of Willie Hutch’s “Tell Me Why Has Our Love Turned Cold” that hits like a cyclone. “Stay Fly” peaked at Number 13 on the Billboard Hot 100. Months later, Three 6 Mafia shocked the world by winning an Academy Award for Best Original Song, thanks to “It’s Hard Out Here for a Pimp,” from the movie Hustle & Flow. —Mosi Reeves

Everything about Toni Braxton’s R&B hit “He Wasn’t Man Enough” is rich: the layers of chimes, claps, and strings in Darkchild’s complex production; Braxton’s singular voice, deep and dark like quality coffee (it had just earned her a $20 million record contract); and the cutting sarcasm with which she delivers a well-deserved wake-up call to her ex’s new lady. “I think he’s just the man for you,” she witheringly tells her. Ouch. Braxton’s timeless read of the song is much of the reason Burna Boy’s ingenious 2022 flip of “He Wasn’t Man Enough” into his own heartbreak anthem “Last Last” made for his biggest song to date — over two decades after the original. —M.C. 

Following their groundbreaking sister albums Kid A and Amnesiac, Thom Yorke asked, “Why so green and lonely?” and gave us the awesomely anxious Hail to the Thief. The album itself divided fans, but it’s impossible to deny the five-minute masterpiece that is “There, There.” Listening to it is like stepping inside Yorke’s frenzied mind, in the same way he ventures into the Bagpuss-inspired forest in the stop-motion video. Layered drums kick off the madness (when Radiohead play it live, Jonny Greenwood brings out the toms, signaling the song, and the crowd goes bonkers) before it climaxes into glorious digi-rock chaos. “It made me cry when we finished it, actually, I blubbed my eyes out,” Yorke said. —A.M.

At the nexus of post-grunge, nu metal, goth rock, and Broadway theater, “Bring Me to Life” is a huge ballad wrought from disaffection. Led by Amy Lee’s soaring vocals and bolstered by a 22-piece string section, this emotional cry cut through the male-dominated angst of early 2000s rock radio, emerging from the Daredevil soundtrack to becoming a Top 10 smash. Lee wrote the lyrics about a run-in with her future husband while faking her way through an abusive relationship. “He just looked me dead in the eye and said, ‘Are you happy?’” said Lee. “I felt like he could just see straight into my soul. That inspired the whole song. Years later I told him it was about him, and the rest is history.” —C.W.

SZA took a bold step forward with “Drew Barrymore,” the lead single from her debut, CTRL, a painfully soulful ballad. Solana Rowe goes for raw emotion as she sings about self-doubt, asking, “Is it warm enough for you inside me?” It was inspired by her painful memories of growing up insecure, relating to Barrymore’s teenage misery in Nineties movies like Never Been Kissed. She summed it up as “seeing girls who have very nice hair and new clothes and sweep the guys you wish you were compatible with off their feet.” Drew herself loved the song — along with everyone else — even appearing in the video. But it established SZA as a major new voice nobody could ignore. —R.S.

“Stoned and Starving” is an aimless epic. Living up to the promise of its title, this mesmerizing 2010s indie-rock classic finds Parquet Courts’ Andrew Savage drifting from bodega to bodega, considering snack options, perusing magazines, and acknowledging the looming specter of mortality with a shrug (“I was holding some wadded bills/I was reading that smoking kills”). The hypnotic toll of the lead guitar riff expands into droning, feedback-heavy jams, and the whole band jumps behind Savage with a jolt on the titular refrain. It’s a shaggy-dog odyssey with no ending, not even a semblance of resolution. Another reminder that, in this life, you can’t get no satisfaction. —J. Blistein

There were plenty of guitar-strumming sensitive guys around in the 2010s, from Jason Mraz to Shawn Mendes, but Ed Sheeran completely eclipsed them all to become one of the biggest pop stars of the century. It all started with debut single “The A Team.” With just his acoustic guitar for accompaniment, Sheeran paints a tragic portrait based on a crack-addicted prostitute he met at a gig he did at a homeless shelter: “I was 18 at the time and quite naive, so I was a bit taken aback by some of the stories,” he said in 2011. That innocent introspection helped shape the song that would launch Sheeran into the singer-songwriter stratosphere. A year after its release, he was opening for Taylor Swift. —M.G.

For a brief, glorious time in the 2000s, bands like Phoenix were making fizzy dance rock and scoring major hits. The French group planted its stake in the era with the 2009 single “1901,” an impressionistic ode to Paris’ Belle Epoque that still sounds exhilarating a decade and a half later. It’s all in the details: tight production with propulsive, Strokes-like guitar work, rhythmic stop-start action borrowed from club music, and synthesizers that spool up like a spaceship attaining warp velocity. Singer Thomas Mars’ lyrics are inscrutable in places, but his chorus is a late-night rallying cry that is guaranteed to evoke joy no matter the context. —J.F.

The debut single from Atlanta-via-Mississippi duo Rae Sremmurd was trap music at its most giddy and ebullient, its menacing bass and machine-gun hi-hats turned into pure pop euphoria. Under the aegis of low-end theorist MikeWillMadeIt (Future, Myley Cyrus), the pair of real-life brothers emerged like a can of Red Bull in the era of lean, a high-octane combination of high-pitched voices, lines emphasized with squeaked or rasped flows, giddy chants, and long-held notes. “We don’t want to just come out and be like, ‘I go to the club, and I have the drugs,’” the group’s Swae Lee said. “We wanted it to be sonically pleasing for your ears, but just be weird as fuck, sounding like nothing else.” —C.W.

Despite being about something undeniably dark — sexual assault — the bouncy, airy, out-there melody of Grimes’ best single seemed tailor-made for the era. “The song is more about empowering myself physically amongst a masculine power, and the hate of feeling powerless, making light of masculine physical power, making it jovial and nonthreatening,” she said at the time. “Oblivion” was a call to vibe out and rainbow your way out of dark times, with a pied piper melody that resonated with other musicians who sought to capture Grimes’ ineffable spirit. —Brenna Ehrlich

Just like 50 Cent’s “In Da Club” is a guaranteed spin at every party, Wisin y Yandel’s “Rakata” stands as an old-school reggaeton staple that never fails to get people dancing. Released in 2005, the Puerto Rican duo’s perreo anthem — produced by Luny Tunes and Nely “La Arma Secreta” — has earned its place in the classic songbook of Latin music. The single marked a before-and-after at a time when reggaeton lived one of its greatest moments. —T.M.

Andrew VanWyngarden and Ben Goldwasser met shortly after the turn of the millennium as students at Wesleyan University. They began creating electro-psych songs for fun, and as a means to express some of their anxieties about post-college life. “We were nostalgic for childhood, and there was the threat of post-college life coming,” VanWyngarden said. This fear is hard to miss in “Kids,” an absurdly catchy song, drenched in synths, about the pains of growing up. “Decision to decisions are made and not bought,” they wrote. “But I thought this wouldn’t hurt a lot, I guess not.” Two decades after they accepted their diplomas from Wesleyan, “Kids” has been streamed more than a billion times on Spotify, and been embraced as the anthem of an entire generation. —Andy Greene

With 2022’s Renaissance, Beyoncé paid tribute to disco and house music with an eye toward honoring those sounds not just as classic musical genres, but also as spaces of queer and Black freedom and resistance. “Cuff It,” the album’s most popular track, was also its most joyful, a disco anthem she co-wrote with a team that included Raphael Saadiq, The-Dream, and Nile Rodgers. Mixing lush strings, Chic guitar, and Rick James bounce, while interpolating Teena Marie’s “Ooo La La La” and nodding to her Texas roots with a command to “hit them ‘draulics,” she came up with a drinks-in-the-air ode to dance-floor abandon that won her a Grammy for Best R&B song. —J.D.

Few bands have managed a cross-generational impact like Los Tigres del Norte. With “Somos Más Americanos,” the norteño legends carried their legacy into the 21st century while doubling down as fierce advocates for immigrants. On the track, they sing from the perspective of an undocumented immigrant, pointing to the history that part of U.S. once belonging to Mexico: “They’ve yelled at me 1,000 times to go back to my land, because I don’t fit here… But I want to remind the gringos, I didn’t cross the border. The border crossed me.” Since its 2001 release, the anthem has become a staple in their live shows — even getting a powerful rendition with Rage Against the Machine’s Zack de la Rocha.–T.M.

A window into the stormy emotional lives of two young fathers became the first Number One single for OutKast, eventually the most successful Southern-rap group in history. “‘Ms. Jackson’ came from just wondering — after a relationship kinda goes to the left — about a parent of a girl who has a child, like, how does she feel about the situation?” said OutKast’s André 3000, who had famously dated R&B superstar Erykah Badu. Originally written by Dré on acoustic guitar, the song took life as a psychedelic ballad slurping with backmasked percussion. Big Boi lashes out as the wounded suitor, André 3000 goes sensitive and apologetic. “How did my mama feel?” Badu said to RapRadar. “Baby, she bought herself a Ms. Jackson license plate.” —C.W.

After her debut, When We All Fall Asleep, Where Do We Go?, Billie Eilish could have just kept coasting as the lovable green-haired teen prodigy, the pop world’s kooky kid sister. But she had darker emotional places she needed to explore — and that’s where she found her new adult voice. “Happier Than Ever” is the devastating title track of her second album, dissecting a poisonous relationship. It starts out as an acoustic ballad, then kicks into rock-guitar distortion. By the end, she’s screaming at the top of her lungs — “Just fucking leave me aloooone!” — in a fit of cathartic feminist-punk rage. “Happier Than Ever” proved how far Eilish could push — an artist who would always refuse to do anything the easy way. —R.S.

Brandi Carlile recorded her second album live to tape with her band and producer T Bone Burnett, and “The Story” — written by her longtime collaborator Phil Hanseroth — clearly benefited from the immediacy. A sweeping statement of love, “The Story” is a solid midtempo ballad that’s elevated to transcendence by Carlile’s vocal performance. She possesses a gently joyous resilience at the song’s outset, but the more she realizes how crucial having someone at her side has been to her long-lived life, the fuller her voice grows, soaring and dipping until it comes fully unglued, revealing the messy realities inside her in astonishing fashion. —M.J.   

Though Rihanna debuted with her Caribbean culture on full display on 2005’s Music of the Sun and kept a reggae through line into her second album, 2006’s A Girl Like Me, by the time she was at the essential pivot point of 2007’s Good Girl Gone Bad, her world and sound had expanded massively. Though subsequent island-tinged hits like “Rude Boy” and “You Da One” were musical homecomings, 2016’s “Work” is a perfect meeting of all the cool she had accumulated over her years at the top of pop music and the Bajan girl she’s always been. Armed with PartyNextDoor’s most resonant songwriting, Drake with the melodies doing what he does best, and her own biting blend of Caribbean creoles, Rihanna has dominated dance floors with “Work” for nearly a decade. —M.C.

After breaking out with their scrappy Southern-Strokes sound in the early 2000s, Kings of Leon hit the mainstream with the brawny ballad “Use Somebody,” a gem off the band’s 2008 breakthrough album, Only By the Night, which also featured the chart-topping “Sex on Fire,” and took home a Grammy for Record of the Year. “You know that I could use somebody/Someone like you,” frontman Caleb Followill sings yearningly as the guitars swell into the song’s climactic peak. The single has amassed more than a billion streams since its release, making it one of the biggest rock hits of the 2000s. —John Lonsdale

Back in the late 1990s, Medellín, Colombia native Juanes left Ekhymosis, his heavy metal band, and decamped in Los Angeles in search of pop-rock stardom. He found it almost immediately thanks to a superlative ear for comforting hooks, and the guidance of producer Gustavo Santaolalla, By the time his second album, Un Día Normal, dropped in 2002, Juanes was a Latin Grammy winner and concert favorite. “Es Por Ti” sums up the Zen beauty of his spiraling, guitar-based melodies, the supple comfort of his guy-next-door vocals, and a sunny cosmovision of disarming sincerity. —E.L.

The explosive lead single from Amerie’s 2005 sophomore LP, Touch, boldly fuses a funky, old-school Meters sample with modern R&B fire. Produced by Rich Harrison, the track rides a frenetic go-go rhythm, which practically hypnotizes listeners into bopping along. Throughout Amerie’s sole Top 10 smash, she fixates on that irresistible thing her partner does that leaves her wanting more. Its deceptively tricky vocal key — which went viral for its difficulty amid the song’s 2025 reemergence — adds to its charm. “[Harrison and I] have a trust sonically,” Amerie said of her relationship with the producer. “When we came together, we really did create something new.” —J’na Jefferson

The emotion-wracked superstar duet was a staple of romance soundtracks for decades, and Lady Gaga brought it into the 2010s with this Oscar-winning team-up with her A Star Is Born co-star Bradley Cooper. In addition to her many other talents, Gaga is one of modern pop’s best power-balladeers, and this folk-tinged love song finds her at her peak; Cooper’s growl is a worthy foil for her wail, which gets to fully unfurl on an extended, wordless vocal run near the song’s end — where a less-brave singer might encourage a bandmate to lay down a guitar solo. —M.J.  

Will Toledo follows a grim road in “Drunk Drivers/Killer Whales,” but like all great Car Seat Headrest songs, it still leads to some inkling of rock & roll catharsis. Here, Toledo ruminates on “post-party melancholia,” a yearning for self-improvement pushing up against a morass of loathing and loneliness. His boldest songwriting choice is drawing parallels between the violent tendencies of orcas kept in captivity (“killer whales” is a reference to the documentary Blackfish) and the self-destructive compulsions that emerge when we’re locked within ourselves. Though an ostensibly easy thing to acknowledge, addressing it is another beast entirely. But Toledo offers a first step on that path in the form of a perfect hook: “It doesn’t have to be like this.” —J. Blistein

The second single from Aaliyah’s third record represented a new phase in her career. While her slippery soprano hadn’t changed, on “Rock the Boat” Aaliyah was using it to express her desire in a more assertive fashion; “Let’s take this overboard now,” she asserts before the first chorus, where she offers up detailed directions on how to ride her waves. Using glitter-flecked synths and sinewy rhythms, producers Eric Seats and Rapture Stewart gave Aaliyah’s bedroom come-on a backdrop that recalls the Quiet Storm era’s most splendorous moments; Aaliyah sets her vocal to simmer, bringing the heat as she reminds the listener that she’s in total control. —M.J.    

According to System of a Down guitarist Daron Malakian, this art-metal collage of whiplash riffs is about perceptions over drug addiction, but its esoteric amalgam of paranoia, fear, confusion, and rage made it a synchronistic soundtrack to the days before and after 9/11 — it’s lines about “self-righteous suicide” even got the song tagged on Clear Channel’s suggested do-not-play memo. “Chop Suey!” became a Billboard Top 100-charting hit, no small feat for a song built around whispers, shouts, disorienting staccato shards and circus-punk blasts. “They can take something that seems really awkward and convey it in a way where you can see it as beautiful,” producer Rick Rubin told Rolling Stone. “It forces you to open your mind.” —C.W.

Katie Crutchfield has spent the past two decades proving that she’s one of indie rock’s greatest songwriters, and this standout shows so much of what she’s good at: a tunefully raw verse that drops you vividly into a headspace, elegantly evocative lines spun like it was nothing, chorus that (no pun) blooms like a small miracle. “Lilacs” was the final song Crutchfield wrote for 2020’s Saint Cloud, the album she got sober while making. That amazing chorus was actually a way to transcend a bad moment. “It was definitely one of those days,” she told Rolling Stone’s Angie Martoccio. “When I wrote that chorus, I was like, ‘All right, we’re going to make this a little bit of a light at the end of the tunnel.’” —Christian Hoard

Crunk&B queen Ciara and future-dwelling MC and producer Missy Elliott showed how they were made for each other on their first collaboration, a sinewy Jazze Pha production from Ciara’s 2004 album, Goodies, that drops her perpetual motion in the middle of the dance floor. (It’s unfortunate use of the r-word hasn’t aged as well.) Pha’s track, inspired by the bare-bones production of the Eighties, is an ideal framing for Ciara’s breathy soprano, which calls out instructions to move gently, yet firmly; Elliott’s ad-libs set up her tongue-twisty verse, which shouts out belter Teena Marie’s similarly funky “Square Biz” while showing that her tastes run the gamut from Jell-O to filet mignon. —M.J.   

Hip-hop at its most beaming and glistening, T.I. rides a synthesizer interpolation of an anthemic Impressions chord progression into the Atlanta sunset. DJ Toomp, a legend of Atlanta bass from its earliest days in the late Eighties, tried sampling the triumphant coda of Roberta Flack’s cover of “Gone Away,” but instead opted to have it interpreted by the Blade Runner-meets-Superfly synths of engineer Wonder Arillo. “I remember when ‘What You Know’ first came out, DJ Khaled called me from Miami and was like, ‘Yo, you guys got a smash! I want you to listen to this crowd, man, when I drop this record, and watch what they do,’ Toomp told Complex. “He dropped that shit and everybody went crazy.” —C.W.

Not long after Girls’ Generation debuted in 2007, South Koreans gave them the honorific title of the Nation’s Girl Group. Their deliciously chaotic pop single “Gee” personifies aegyo — or the use of cute, childlike mannerisms to charm others. Snare drums and Eighties-era synths complement the song’s slumber-party vibe, creating a hopped-up earworm from start to finish. The song’s title is used as a filler word throughout the fast-paced electro-pop number. “So electrifying, my body trembles,” they sing about their collective crush. But after giving themselves a moment to process their one-sided infatuation, they exhale an ebullient “gee gee gee gee gee.” Cute boys will come and go, but Girls’ Generation is forever!  —J-H.K.

In the summer of 2001, emo-rockers Jimmy Eat World delivered one of the century’s catchiest pop-punk anthems with “The Middle,” an addictive motivational rocker off their fourth album, Bleed American. “The Middle” still resonates decades later, thanks to its reassuring, karaoke-beloved chorus: “It just takes some time/ Little girl, you’re in the middle of the ride/ Everything, everything’ll be just fine.” As frontman Jim Adkins said during the band’s NPR Tiny Desk performance in 2020, “Your sense of self-worth coming from external validation is just kind of an empty pursuit.” —John Lonsdale

When country-radio fans heard the lead single from the then-Dixie Chicks’ 2002 album, Home, their ears perked up. It just didn’t sound like what was coming out of Nashville at the time. There were elements of bluegrass, a more organic level of production, and singer Natalie Maines’ cutting vocal. Written by Darrell Scott, himself a bluegrass picker, “Long Time Gone” took country music to task for losing its soul, and the Chicks’ punky approach to the track gave it even more bite. “They sound tired but they don’t sound Haggard/They’ve got money but they don’t have Cash,” Maines declared near the end of “Long Time Gone,” reclaiming the real country music of the past. —J.H.

“Espresso” was the endlessly meme-able breakout smash from a former Disney kid who’d already made five albums. In the studio with her producer Julian Bunetta, Sabrina Carpenter knew this “stupid little song” was her key to pop glory. “You’re not writing a song with ‘Well, everyone’s going to have to understand this’ in mind,” she said. “You’re just like, ‘What sounds awesome? What feels awesome?’” an ethos that led to brilliantly head-scratching rhymes like “Mountain Dew’d” and “dream came true’d.” This yé-yé-flavored sugar rush was an irresistible summer jam, yet it may be better remembered as our introduction to music’s next great lyrical provocateur. Somewhere, Serge Gainsbourg is smirking. —S.G.

No one asked Jay-Z and Linkin Park to make a mashup project, but it’s hard to resist how fun the final EP turned out to be. Inspired by Danger Mouse’s recent Jay-Z-meets-Beatles project, The Gray Album, the Brooklyn rap legend reached out to the successful rap-rock outfit to make something unique of their own. “Numb/Encore” was the only official single, an absolute monster in delivering the fusion of their two artistic worlds. Instead of merely tinkering with the original tracks, Jay-Z and Linkin Park decided to record the mashups together in the studio, creating a more seamless coalescence of their individual hits. Jay sounds like a natural fitting his classic hip-hop cuts into LP’s alt-rock sound. —B.S.

The four resident rebels of Café Tacvba spent most of the Nineties rewriting the Latin-rock rulebook, fusing norteño roots with punky humor, Beatlesque harmonies with huapangos and avant-garde boleros. And then they wrote a simple love song. This shocking plot twist — a heartfelt ballad — was almost as radical as their collaboration with Kronos Quartet. Even more brilliant: the Mexico City band’s biggest hit was sung not by lead singer Rubén Albarrán, but by its composer, keyboardist Emmanuel del Real. It’s not the most ambitious chapter of their extraordinary songbook, but definitely the most emotionally compelling. In 2025, del Real spread his wings in full as a singer-songwriter with a spectacular solo debut. —E.L.

Back in the early Nineties, it would have been absurd to expect anything profound or philosophical from the band who gave us “She Don’t Use Jelly.” But the Flaming Lips grew and matured in surprising ways, both musically and spiritually, and they delivered a stunning anthem on 2002’s Yoshimi Battles the Pink Robots — which frontman Wayne Coyne said was about “how precarious our whole existence is.” This sentiment echoes throughout the song with lines like “Do you realize the sun doesn’t go down/It’s just an illusion caused by the world spinning ’round.” In 2009, the state of Oklahoma named it the official state song, beating out nominees like J.J. Cale’s “After Midnight” and Elvis Presley’s “Heartbreak Hotel.” —A. Greene

Lycanthropy was in the air circa 2006. The same year Stephanie Meyer was titillating teens with the introduction of werewolves into her Twilight series, TV on the Radio were showing hipsters the transformative power of desire with tantalizing ferocity on “Wolf Like Me.” The song moves at an insatiable clip, tractor-beam guitars and Tunde Adebimpe’s words — “My heart’s aflame, my body’s strained, but, God, I like it” — building to a climax that, like many great pleasures, is briefly delayed when the bottom drops out into a practically dreamy bridge. The wait is, obviously, worth it. After one more ardent verse, “Wolf Like Me” ends with one of the great shout-along outros, a ravenous proclamation: “We’re howling forever, oh oh!” —J. Blistein

The song that moved the phrase “Are you drunk right now?” into the heart of the pop lexicon. Released at the onset of Drake’s imperial era (2011-16), “Marvins Room” turns a late-night drunk dial into a neo-noir confessional, the camera gliding across postparty detritus before finding our protagonist glaring forlornly into a golden chalice, pining. Noah “40” Shebib’s beat is vaporous, and Drake’s at his neediest, but the result is alchemical, magical — and massively influential. Drake was already a star, but Take Care solidified his influence on R&B, inspiring a decade of sine-wave production flourishes and frankly emo bloodletting. “Marvins Room” is the apex of this mode: tuneful, embarrassing, indelible. —C.P.

“Cruel Summer” was the immediate standout on Taylor Swift’s 2019 album, Lover, co-written by Jack Antonoff and St. Vincent. Everyone figured she was saving it to be her summer jam of 2020 — until the pandemic shut down that scenario. So it seemed like this tune just got stranded in time. But you can’t keep a great song down. “Cruel Summer” finally made the charts and hit Number One — in October 2023, four years after it came out. It combines so many of Swift’s favorite ways to spend a Saturday night — sneaking out of windows, crying all the way home from the bar, suffering through a doomed romance, but enjoying every moment of the torture. —R.S.

Chief Keef’s breakout single hit the Windy City like a hurricane. Keef had been making music for several years before “Don’t Like,” but the mesh of Young Chop’s spooky, unforgettable keys with Keef and Lil Reese’s raw treatises of what Chicago’s drill scene was all about spoke for a generation of jaded kids who were alarmingly detached from emotional depth, but in tune enough to know, “a snitch nigga, that’s that shit I don’t like.” Keef showed his effortless hitmaking ability, while several MCs “borrowed” Reese’s stutter flow for a couple of years. Drill music now has offshoots all over the world, and most could trace their first glimpse of the sound to this song. —A. Gee

Modest Mouse came up in the Nineties indie-rock scene, yelping about paranoia, decay, and American rot. By 2003, they were unraveling for real thanks to label battles, booze, and Bush 2.0. “I was just kind of fed up with how bad shit had been going,” frontman Isaac Brock said. So he tried writing something useful — a chirpy singalong for slamming your head against the steering wheel. “I backed my car into a cop car the other day/Well, he just drove off — sometimes life’s OK,” Brock sings. The guitars tick ahead, brushing off each calamity like a ball of lint. When “Float On” dropped in early 2004, its loopy optimism blew up, giving the band its first Modern Rock Tracks chart Number One, a Grammy nomination, and the distinction of showing an anxiety-riddled nation how to stay afloat. —S.G.

With good kid, m.A.A.d city, Kendrick Lamar showed the world the type of introspection that’s made him a hip-hop visionary. The album plays out like a screenplay unfurling in Kendrick’s subconscious — the moments that defined his life are intertwined with his present-day success and stories going back generations. It all comes together on “Money Trees,” a track so densely packed with intricate songcraft that he would forever be known as hip-hop’s patron saint of multilayered storytelling. Over the transfixing sample of Beach House’s “Silver Soul,” Kendrick set the stage for a career spent laying truths bare. —Jeff Ihaza

Trent Reznor originally wrote and recorded it with Nine Inch Nails in 1994, but Johnny Cash made “Hurt” all his own, thanks to the stark production of Rick Rubin, a haunting music video, and the Man in Black’s own late stage in life — he recorded his version of the song just a year before he died in 2003. Originally released on Cash’s 2002 LP, American IV: The Man Comes Around, the song caught fire when its video, directed by Mark Romanek, was sent to MTV. Juxtaposing images of a ruminative Cash, trembling and frail, with archival clips of the country singer in his prime, it gave “Hurt” a whole new meaning. This is a list of the best songs, but at least in this case, its power is forever tied to the video. —Joseph Hudak

Tom DeLonge and Mark Hoppus traded speedy pop punk for somber acoustic guitars, drummer Travis Barker put down his sticks and grabbed some brushes, and Blink-182 ended up with one of the most beloved songs in their catalog. “I Miss You” found the band going for an intimate orchestrated sound in the vein of sad alt-rock titans like the Cure (fittingly, the song appears on an album that also features a cameo from Robert Smith). The result is a polished track that provided perfect backing for the stark vulnerability and mature candor of DeLonge and Hoppus’ lyrics. —M.G.

Alicia Keys’ debut single is still her signature for a reason: The soulful cut highlights Keys’ strengths as a singer, pianist, songwriter, and producer. Just 20 when the track was released, Keys sings of the emotional turbulence of being in love with someone with wisdom and pain beyond her years, with the type of emotive runs built for car sing-alongs and karaoke rooms for decades to come. The track hit Number One on the Billboard Hot 100 and won Song of the Year at the Grammy Awards. “I was going through it bad,” Keys said of the relationship that inspired the song. “But it helped me work things out.” —B.S.