The 250 Greatest Songs of the 21st Century So Far

Every era gets the lighters-up, power-ballad, arena-rock anthem it deserves, and for the early 2000s, Train delivered with “Drops of Jupiter.” It was a Top Five hit in the summer of 2001, but it’s just gotten more ubiquitous over the years. Pat Monahan belts poetic questions like, “Tell me, did Venus blow your mind?” He was inspired to write it by his late mother, after waking up from a dream about her returning from the cosmos. Train had other hits, like “Hey, Soul Sister,” but “Drops of Jupiter” has taken its place as a true standard, the closest this era has gotten to a “Don’t Stop Believin’” or “Africa” of its own. In other words, it’s the music equivalent of the best soy latte that you ever had. —Rob Sheffield

Tweet’s biggest hit was well ahead of its time. Produced by the ever-future-forward Timbaland and co-written by Missy Elliott, the song takes on self-love over a hypnotic, techno-reggae beat. Tweet was inspired to write the song after watching an episode of Oprah where a doctor advised people to start looking at themselves naked in a mirror to learn self-acceptance. Tweet takes this to sultry levels, describing the experience of coming home after a night out and discovering that it was her own body that left her breathless. And while most interpreted the sexy, intoxicating track as being about masturbation, Tweet has maintained it’s about however one learns to love the body they’re in. —Brittany Spanos

Fleet Foxes’ 2008 debut is full of radiant vocal harmonies, but they all fall away on this stunning solo showcase for frontman Robin Pecknold. Singing over a spare, mournful folk guitar part that feels like it could be centuries old, he sketches a “Scarborough Fair”-style scene of medieval wanderers on a cold morning before making his way to a gravesite and crying out in spiritual pain: “Dear shadow, alive and well/How can the body die?” It’s a starkly evocative outburst, even if Pecknold would later downplay “Tiger Mountain Peasant Song” as a young man’s work. “I think those songs were stories mostly because I was 20 years old writing them and had few life experiences to draw from!” he said in 2020. —Simon Vozick-Levinson

In the early 2010s, EDM conquered dance floors worldwide — everywhere except America. Then came Tim Bergling, a babyfaced Swedish teenager who went by Avicii, named for the lowest level of Buddhist hell, where souls get a shot at rebirth. His weapon? “Levels,” a euphoric piano and synth progression built around Etta James’ gospel classic “Something’s Got a Hold on Me,” was like pouring a can of Monster down the ear canal of the nation. After 2011, it blared everywhere with baffling appropriateness: Coachella, Buffalo Wild Wings, your nephew’s elementary school graduation. “You’re the John Coltrane of Fruity Loops,” Chic’s Nile Rodgers said to Bergling. —Sarah Grant

Country-rap troubadour Post Malone and Rae Sremmurd party starter Swae Lee teamed up like Tony Stark and Peter Parker for the soundtrack to Spider-Man: Into the Spider-Verse, creating a breezy, dreamy, melancholy tune that dominated our universe’s Top 10 for 33 weeks. Written and recorded around 6 a.m. after a long collaborative session between Post and Swae, the two-minute-and-38-second song would be sung by Spider-Verse protagonist Miles Morales while working on some art in his bedroom. The movie would end up the Number One film in the country, helping “Sunflower” grow to be the first digital song certified double diamond by the RIAA. —Christopher R. Weingarten

Whereas Daddy Yankee and Don Omar loomed as the obvious candidates for reggaeton stardom, Tego Calderón brought forth something entirely different: a touch of salsa legend Ismael Rivera, not in sound, but in his throaty flow — rustic to the bone — and the ease with which he handled a barrage of Puerto Rican slang. “Pa’ Que Retozen” is the hedonistic megahit of his 2002 revolutionary debut, El Abayarde. It brims with humor and self-confidence, pinning the beat against serrated lines of bachata guitar. At a time when Latin music was learning to paint with a new set of colors, Calderón emerged as the genius-next-door, a master of shading. —Ernesto Lechner

“Shadows are fallin’, and I’m runnin’ out of breath,” sings Warren Zevon in this song’s first line. By the time he was making The Wind, Zevon had been diagnosed with terminal cancer and decided to carry on with what would be his final studio record. On this beautifully stoic and gentle lullaby to himself and his legacy, co-written with longtime collaborator Jorge Calderón, Zevon doesn’t sound like the wild man he once was. But with the sympathetic thump of drummer Jim Keltner behind him, he wants to reassure everyone that he’ll still be around in one form or another once he’s gone. If you hear a line like “You know I’m tied to you like the buttons on your blouse” and don’t tear up a bit, you really are a werewolf with no soul. —David Browne

Big tribal vibes inform this illuminative 2023 anthem. The teeming chorus and rustic percussion of this poignant single from the Lagos, Nigeria, representative’s fifth LP resound like a vigilant village in motion. When’s the last time a song about being aloof went bonkers on the charts? For all of its “left-on-read” insistence (with a hearty declaration that “I can’t talk”), “Unavailable” reached Number Three on the Billboard U.S. Afrobeats Songs chart. Davido’s fiery tenor feels intimate and expressive as he reflects on his busy rock-star life, not without a touch of regret. “I’m changing my life, oh/Got my mama proud, innit?,” he proclaims. This smart single about ghosting is indeed haunting. —Will Dukes

One of the most evocative and emotionally rich lyricists in hip-hop history was far from home when he painted this picture of his Southside Houston neighborhood. Hired by Russell Simmons to lead his Def Jam South imprint, Scarface recorded much of his lone mainstream-adjacent album, 2002’s The Fix, in New York City. “Being in New York … can change the outcome of anybody’s records and thought process,” Face told Complex. A combination of bittersweet reminiscences and a loping piano loop from a Roberta Flack and Donny Hathaway record, “My Block” was narrow in scope but universal in substance: “On my block, it’s like the world don’t exist/We stay confined to this small, little section we living in.” —C.W.

A quarter century later, the song that Brendan B. Brown wrote, in part, about a grisly murder in the Long Island town in which he grew up is now a karaoke standard and Y2K signpost. But between Brown’s third-verse falsetto to his evocation of Eighties adolescence (Keds, tube socks, shitty Camaros), the song’s dated specificity has actually helped it endure. Covers and interpolations from One Direction, SZA, and Rod Wave have given the song a new Gen Z resurgence, while Weezer has continued to increase its global appeal by covering the song that many assume they wrote. “Whatever drove people to the song,” Brown told Rolling Stone in 2020, “is way more important than some satan murder in my hometown.” —Jonathan Bernstein

Mac Miller never sounded as self-actualized as he does on the introspective track from his 2018 album, Swimming, which came out months before his untimely death. On “2009,” a wistful Miller reflects back on the pivotal year before he dropped his first label-released mixtape, K.I.D.S., and offers nuggets of wisdom like “Life ain’t a life until you leave it.” But it’s the careful selections Miller made that mark “2009” as the epitome of his musicianship: The rapper folded in the piano motif from Chanté Moore’s Nineties hit “Got a Man” and a vibraphone to achieve a soulful vision that reflects his lasting legacy. —Maya Georgi

“Bangarang is probably the furthest thing from brostep, because the tempos aren’t even dubstep tempos,” Skrillex explained in 2014. He was talking about the EP as a whole, but the title track makes his point all by itself. It’s a frisky, hip-hop-tempo track that builds on the piledriving low end of his career-making earlier works, but turns all of it into hooks. It was a clear signal that the guy that underground types pilloried as a one-trick pony — indeed, as Skrillex pointed out, “brostep” was not a term of endearment at first — had a lot of facets to show. —Michaelangelo Matos

Jack Antonoff has spent this century writing hits with the biggest names in music, from Taylor Swift to Lana Del Rey to Lorde. Meanwhile, he’s also fronted Bleachers, where the New Jersey native often channels the grandeur of Eighties radio-rock and New Wave through an indie-pop lens. He never did it so powerfully as on “I Wanna Get Better,” a statement of emotional purpose after the national tragedies of 9/11 and the Iraq War, and the death of beloved family members. Against urgent piano stabs, Antonoff sings about feeling “froze in time between hearses and caskets,” before the song lifts into its anthemic better-getting chorus — as he called it, “a fucking life story in three minutes.”–Jon Dolan

Kid Cudi enjoyed a symbiotic relationship with Kanye West for a few years — it’s hard to imagine Cudi existing without Late Registration, but it’s hard to imagine 808s and Heartbreak existing without Cudi. His 2009 debut, Man on the Moon: End of the Day, was his attempt to forge his own path, and “Day ‘n’ Nite” was its centerpiece, a Geto Boys riff dripping with Drive-wave synths and arena-ready sonic spacing. The lyrics — a paean to insomnia, smoking weed, and determined solitude — feel ripped from the very MySpace ecosystem that Cudi used to launch his career. The result is a track both about and for the nighttime, as well-suited blaring from nightclub speakers as it is quietly playing from headphones on a night bus to nowhere. —Clayton Purdom

Songs that fuse disparate genres can sometimes feel forced. But even with six songwriters chipping in, “A Bar Song (Tipsy)” is the most seamless and rollicking blend of despondent country and shout-along hip-hop imaginable. Everything you’d want in a country song is here: references to alcohol brands, a narrator with the low-wage job who can’t afford to buy his girlfriend that expensive handbag, and a singer whose voice can dip into a pained lower register. With its hands-in-the-air energy, the chorus is a jolt of desperate escapism that the narrator so desperately needs. Plus, how can you hate a song that ends with a funny spoken finale of “…bro, they kicked me out the bar”? —D.B.

In the 1990s, Foo Fighters notched nearly as many alternative-radio hits as Dave Grohl’s previous band, Nirvana. As the 2000s came around, and rock got harder, the Foos fit in effortlessly. Written during a tumultuous period for the band, which was still finding its way as a unit, 2002’s “Times Like These” is textbook Foos — layered guitars supporting Grohl’s upper register punctuated by syncopated chords — with lyrics meant to evoke a sense of resilience and hope. Its chantable chorus, “It’s times like these you learn to live again,” is so easily applied to any hardship that it’s become a calling card as relevant to political candidates (President Biden in 2021) as it is to someone in recovery. In other words: a universal message in any time. —Shirley Halperin

From the beginning, Colombian pop innovator J Balvin showed a tastemaker’s ear for electronic textures and seductive genre hybrids. In the case of “Mi Gente,” the moody, exotic motif in the intro was already present in Willy William’s “Voodoo Song,” which Balvin transformed into a bilingual moombahton anthem, with everyone-is-welcome lyrics about joining a universal party. By the time the soulful Beyoncé remix dropped in the fall of 2017, “Mi Gente” had become the kind of cosmopolitan dance-floor scorcher that had the grooves of Latin America reverberating in every corner of the world. —E.L.

Before his death in 2020 gave the song added gravitas, “Summer’s End” was the standout on John Prine’s triumphant final album, The Tree of Forgiveness. Over a simple, sweet melody, Prine deploys beautifully vivid imagery (swimsuits on a clothesline, the moon and stars shooting the breeze) to sing about love, mortality, and time passing. Following Prine’s death, it became an instant standard, covered by Phoebe Bridgers, Adrianne Lenker, Jackson Browne, Valerie June, and others. Co-writer Pat McLaughlin started the song off with the late-summer imagery before Prine chimed in: “Let’s throw in lawyer’s talk,” he remembered saying. “So we put ‘per our conversation,’ like we’re getting charged by the hour.” —J. Bernstein

Virality often threatens to cheapen great music, but the reason Tems’ “Free Mind” became so inescapable — especially on places like TikTok and Instagram — was because the Nigerian singer-songwriter’s visceral yearning for peace on the song resonated with many people, particularly Black women. It was one of her earliest tracks, a cut from her debut EP, 2020’s For Broken Ears, from which Future lifted her “Higher” hook for his own Grammy-winning smash, “Wait 4 U.” But years later, that success brought the masses back to Tems’ original masterpiece “Free Mind,” and from there, she became one of the continent’s brightest stars. —Mankaprr Conteh

The rise of “bro country” in the early 2010s was accelerated by this 2012 ode to hitting the open road in a “brand-new Chevy with a lift kit,” the radio turned all the way up. Florida Georgia Line members Brian Kelley and Tyler Hubbard had been fine-tuning their blend of swaggering post-grunge and twangy pop with producer Joey Moi for years when they realized the summer-song ideal with “Cruise,” which added hip-pop grooves to its bright-eyed flirtations. Its monster success opened the door for other country dudes to break out the drum machines, while its remix with St. Louis MC Nelly helped Florida Georgia Line come out of the gate with a crossover smash. —Maura Johnston

Atlanta’s Mastodon came up with the greatest metal riff of the new century, a heavily syncopated, wave-chopped two-bar menace. Opening Leviathan, their conceptual opus about capturing Moby Dick, “Blood and Thunder” helped raise the flag for a new generation of sludge-metal bands that treated the subgenre with more prog precision. The percussive riff, naturally, was written by the drummer. “Brann [Daillor] came up with that,” Mastodon guitarist Bill Kelliher told Guitar World. “[H]e’s about as good at guitar as I am on drums — which is to say, terrible — but he comes up with a lot of riffs, and puts them into my hands. The thing is, he thinks of rhythms differently than I would.… This was jagged, angular, and weird, but all of a sudden it clicked.” —C.W.

Dallas’ Old 97’s were initially lumped in with the alt-country scene, but by 2001’s Satellite Rides, they had turned into something else: an ace pop-rock band. Inspired by a brief romance with Winona Ryder, “Rollerskate Skinny” finds frontman Rhett Miller piling up lines both boyishly endearing (“You’re pretty as a penny”) and caustic (“Wouldn’t be here if the Athenia hadn’t sunk”). It’s joyfully buoyant, but with an ache at its center, summed up by its final line, which Miller stretches out till it sounds almost like an affirmation: “I believe in love, but it don’t believe in me.” —J.D.

Rema tapped into traditionalist Afrobeat rhythms on this delectable hallmark dedicated to the fairer sex. The Nigerian wunderkind’s striking lyrics (“I’m in love with plenty women, I no mind marry all of them”) and pop-star allure ensured that his commitment-ditching modal missive surpassed 50 million Spotify streams. The song’s trance-friendly sheen, heartened by a loud, gallop-y stomp, underscores the declarative finesse in Rema’s timbre as he efforts toward an unstoppable chorus. “Woman” is both earnest and acidic — its big-hearted spiciness, wherein playboy vigor meets love-worn diligence, is a big part of its charm. Call it a polyamorous pop stomper for the ages. —Will Dukes

It didn’t take long for this album track off Tyler Childers’ debut album to become the fan-favorite standout and his most-streamed song on Spotify. It’s a perfect little country song, from its multi-hook-laden chorus to its rural romanticism to Childers’ phrasing in the first verse (listen to how he wrestles meaning out of a single word: religious). Childers later began donating royalties from the song to Native communities and indefinitely retired it from live performances because its title (which references an outdated design on a belt buckle he once owned) felt harmful to Indigenous people. But Childers’ rock-star move to retire his most-beloved song has only added to its mystique. —J. Bernstein

Even when they were hellbent on being seen as a pop-punk band, 5 Seconds of Summer were destined to bring everything that made them great to mainstream pop — no caveats, no boy-band labels, no try-hard routines. The lane was wide open, and “Youngblood” slammed down on the gas. The New Wave-influenced record is perfectly assembled around live drums, rhythmic guitar riffs, and an incessant bass line. 5SOS mined the haunting and desperate agony of a destructive relationship and injected it into an exhilarating hit, swelling both sonically and emotionally, bypassing drunk texts and going straight for late-night calls as addictive as its chorus. —Larisha Paul

Bright Eyes’ Conor Oberst often got pegged as something of an emo-folk new Bob Dylan in the early 2000s, and he never embodied that weighty comparison so much as he does here. The tender song about being hopeful in new love even cleverly uses the same chords as Dylan’s decidedly less optimistic “Don’t Think Twice It’s Alright.” Throughout the song, you can almost hear the same melody pierce through. “I wanted to do something stripped down,” Oberst told Rolling Stone in 2002. With just Dylan’s twinkling chords to cruise on, the singer-songwriter’s voice cracks as he delivers simple, yet effusive lines like, “I could go anywhere with you/And I’d probably be happy.” The result is the prolific artist’s sweetest song, and his most popular. —M.G.

Swedish sibling duo the Knife’s 2002 electro-pop gem “Heartbeats” is a love song that zooms in on a fleeting fling, rendering a brief encounter with the grandeur of the eternal. You can see the shape of pop to come in its dazzling array of synths, which undulate and glow, sparkle and strobe, while gated toms ripple across the mix. Vocalist Karin Dreijer situates the song in that timeless space where a memory so potent makes the past feel present. It creates an ecstatic rush, but also a kind of hopelessness. “To call for hands of above to lean on/Wouldn’t be good enough for me,” goes the hook, at once a plea for release, and another to relive. —Jon Blistein

Kanye West essentially assembled the Avengers of pop music for “All of the Lights” and impressively assembled them like a voltron rather than a slate of superheroes shining on their own. If you didn’t know better, you might think Rihanna, with her searing hook; Kid Cudi, with his mantra on the bridge; Fergie, with her lightning-quick rap sequence; and Alicia Keys, with her belted ad-libs, were the only features. Yet under what may be West’s most inspiring, invigorating, and empathetic production and performance laid Elton John, Drake, The-Dream, Charlie Wilson, John Legend, Ryan Leslie, Elly Jackson, and Tony Williams, too. —M.C.

Paul Simon is as pure a writer as rock has given us — he once explained to Rolling Stone’s David Fricke that it took him three full months to write “The Boy in the Bubble,” from Graceland. (Fricke’s priceless response: “What’s that, about a word a day?”) It stood to reason, then, that Simon would be the one to come up with “Rewrite,” a joyous gem from his late-career highlight So Beautiful or So What. “I’ve been working on my rewrite, that’s right — gonna turn it into cash,” he asserts on the frisky chorus. The verses paint a different story — this is the first-person tale of an “old guy working at the car wash” promising to finish the project he’s been talking about forever. —M.M.

The cliche of an album “being as good as a novel” actually usually fits with records by the Mountain Goats’ John Darnielle, especially the band’s 2002 album, Tallahassee, which tells the story of a doomed married couple in a Florida house out of Edgar Allan Poe drinking themselves into mutual oblivion. It peaks with “No Children,” one of the most convincingly hateful I-wish-we-could-break-up screeds ever written. “And I hope you die/I hope we both die,” Darnielle sings with scorched-earth fervor. He was inspired, somewhat diabolically, by Lee Ann Womack’s then-huge country hit “I Hope You Dance,” a song he hated and parodied by changing “dance” to “die.” —J.D.

“Tik Tok” was the perfect introduction to the party-animal persona of Kesha’s early music, and its carefree energy still shines 15 years later. The debut track from Kesha opens with the line “I wake up in the morning feeling like P. Diddy.” But after allegations surfaced against the producer, Kesha flipped the lyric into a bold, crowd-shouted “fuck P. Diddy” at live shows. “Tik Tok” was an era-defining record for the early 2010s, downloaded 610,000 times in its first week, which set a record for a single by a female artist. At the time, the most downloaded song in one week was Flo Rida’s “Right Round,” which had Kesha on the hook. —Tomas Mier

What do ancient holy wars, the golden era of TV, and carbon footprint have in common? Father John Misty. Josh Tillman’s 2015 masterpiece, I Love You, Honeybear, is a concept album about falling in love while the world is falling apart, and it all culminates on the gorgeous penultimate track, “Holy Shit.” He rattles off fiery lines like “Eunuch sluts, consumer slaves/A rose by any other name” and “No one ever knows the real you and life is brief.” But he can put all that despair aside, because he’s found his person. It’s a twisted love song, one Tillman wrote on his wedding day, that remains his most brilliant piece of songwriting. —Angie Martoccio 

If you wanted to pinpoint the big bang of pop music’s Auto-Tune era, you could do worse than “I’m Sprung,” the infectious first single by T-Pain. Eventually, the self-proclaimed “rappa turnt sanga” would become synonymous with the pitch-correcting technology. But on “I’m Sprung,” it feels like a eureka moment, enlivening millennial pop-rap signifiers (see acoustic guitars) with an army of eerily perfect, harmonizing T-Pains. Despite the fact that the track is basically just complaining about being in a relationship (“she got me doin’ the dishes,” he croons, amazed), it’s all surprisingly sweet, a guy lost in the clouds and wondering how he got there. There’s probably less Auto-Tune than you remember, too, but what’s there transformed popular music. —C.P.

“I wanted something to represent the ’hood that sounded authentic, but when you compare it to the average song on the radio, it would feel larger than life,” said Atlanta producer Polow Da Don about his shoegaze-bass insta-classic “Throw Some D’s.” ”Like it cost some money to produce.” Built on a skipping sample of Switch’s luxurious 1979 R&B hit “I Call Your Name,” Polow and Alabama wordsmith Rich Boy went full IMAX on this shimmering ode to flashy Dayton wire wheels. An absolute sensation at the time, it seemed that every rapper — Kanye West, André 3000, Lil Wayne, Rick Ross — wanted their shot at riding on a remixed version of Polow’s rims. —C.W.

This song took a forked path to the top of the country charts. “Wagon Wheel” began as an unfinished song by Bob Dylan from the 1973 Pat Garrett and Billy the Kid soundtrack sessions. Critter Fuqua, of the Nashville string band Old Crow Medicine Show, heard the song on a bootleg when he was a teenager, and the band recorded it in 2004, adding lyrics, since the original didn’t have any, and splitting writing credits with Dylan, who they’d never met. Their lovely fiddle-steeped treatment became one of the century’s great sing-along country gems, and eventually a Number One hit when Darius Rucker recorded it in 2013. —J.D.

If there was a hall of fame for most-quotable lyrics, “Truth Hurts” would be a shoo-in. The 2017 single was much of America’s introduction to the polymath born Melissa Jefferson thanks to its viral resurgence in 2019 and a barrage of brash, meme-ready bars. Though the booming, piano-led trap beat and Lizzo’s naturally comedic delivery keep things buoyant, the song emerged out of heartbreak. “The whole beginning of that session was just venting about the situation with this guy and me taking down notes on what she was saying, because the things she said were funny or outlandish,” producer-songwriter Ricky Reed recalled. Lizzo rebounded with her Minnesota Viking and then raced on to global stardom, which is a helluva way to get even. —Jon Freeman

The Hold Steady have written a pile of this century’s toughest rock & roll songs. But it’s hard to think of another one while “Killer Parties” is playing — the knockdown climax to their 2004 indie debut, Almost Killed Me. The Brooklyn-via-Minnesota bar-band dudes bash out an anthemic ode to watching your twenties swirl down the drain, with nothing to show for your wasted youth except killer parties you can’t even remember. They blend wide-screen Springsteen passion with Replacements-style wit, as Craig Finn splutters his barstool poetry (“killer parties almost killed me”) over Tad Kubler’s enormo-dome guitar. But like so many Hold Steady songs, it’s about lost boys and girls in America, with nothing to believe in except each other. —R.S.

Taylor Swift was only 17 when she sat on her bedroom floor and refashioned the tragic ending to Shakespeare’s Romeo and Juliet into what would become her breakout hit. It only took 20 minutes for her to channel the Bard — and her own teenage angst over her parents’ disapproval of a boy she liked — into a country-pop romp that is still being used to soundtrack marriage proposals. (Nearly every night on Swift’s Eras Tour, multiple proposals happened in the audience while she performed the song.) With a climactic, yearning-filled bridge of over-the-top proclamations (“I love you and that’s all I really know”), “Love Story” is a peak example of Swift flexing her songwriting superpowers, and it remains the most fearless fairytale she’s ever written. —M.G.

If the Bad Boy Records hits of the Nineties taught us anything, it’s that disco is eternal. To wit: We will likely be hearing “Kiss Me More” for the rest of our lives, an easy fit alongside “Get Lucky” on the playlist of any wedding DJ unafraid of having a room full of people yell, “I — I feel like fuckin’ something!” Doja Cat cut a sardonic figure across her early records, her DGAF flow just as comfortable talking shit as it was topping pop charts, but “Kiss Me More” is strikingly unified, thanks in part to SZA’s characteristically high-rizz guest verse. The result was a four-quadrant hit that ended up breaking records with its longevity. —C.P.

As Brittany Howard told NPR about the Alabama Shakes’ breakthrough hit, the first audience that heard the band working out “Hold On” onstage immediately joined in with its improvised chorus. “They thought it was a cover song,” she said, “so they started singing it with us.” That crowd response speaks to why the song became an immediate classic. It feels familiar — a bit of soul, a hint of blues — yet isn’t beholden to either genre. “Hold On” also sported lyrics anyone could understand — about leaving your teens behind, taking on new responsibilities, and wondering if you were up to the task — along with a taut guitar groove and a Howard vocal that still grabs you by the lapel more than a dozen years later. —D.B.

“Yeah!” wound up heralding the arrival of Usher’s album Confessions after Lil Jon leaked it to DJs in late 2003. The song caught fire, and eventually there was no choice but to make it the lead single. All these years later, “Yeah!” still hits with unmitigated delirium: the blaring synths and booming bass, Lil Jon’s inch-perfect ad-libs, Ludacris’ hall of fame feature, and Usher spinning crunk&B gold with a spicy club drama about a guy struck dumb by the realization that the baddie coaxing him onto the dance floor is his girl’s ex-best friend. The angel and devil on his shoulder duke it out for a few minutes, but there was only ever one answer to this conundrum. It’s right there in the title. —J. Blistein

A riveting, tawdry telenovela in the guise of a four-minute hit, “Ella y Yo” finds Don Omar admitting to his best friend, Aventura heartthrob Romeo Santos, that he has been conducting a guilt-ridden affair with his wife. Not surprisingly, the 2005 visual is a tad histrionic, but the main attraction here is the brilliant interpolation of a lilting, spidery bachata into the gritty, old-school reggaeton groove. The contrast between Santos’ mellifluous crooning and Omar’s gruff vocals amps up a stylistic clash that, at the time, felt nearly apocalyptic. —E.L.

Following the success of her sister Jessica and her husband, Nick Lachey, on MTV’s Newlyweds, Ashlee Simpson signed on for her own reality show, which focused on the recording of her first album. Ashlee’s debut single,” Pieces of Me,” arrived in 2004 as a polished mix of pop and rock that captured her own voice and set her apart from her sister. It became a breakthrough, climbing to Number Five on the Billboard Hot 100, her highest-charting single. Had the infamous Saturday Night Live lip-syncing incident not occurred, Ashlee’s trajectory might have been very different. In its moment, “Pieces of Me” hinted at a different future, her raw vulnerability and punk-pop edge could have fueled a long run. —Alison Weinflash

When Rich Homie Quan started working with Young Thug, he was so jazzed with the sessions he claimed they’d be “the best collabo since OutKast.” Cash Money label head Birdman apparently agreed. After launching Rich Gang as a supergroup, he reconfigured it as a showcase for the new duo, who continuously goad each other into ever-more-elastic, emotive bars across the project. All of this is immediately apparent on their 2014 debut single, “Lifestyle.” Thug’s Dadaist delivery etches out indelible melodies, Quan’s rugged wordplay grounds the tracks, and the resulting effect is as exuberant as it is melancholy. Quan was right: You don’t even have to squint to draw a line back to Aquemini. —C.P.

A song so addictive that it enticed (what seemed like) the entire South Korean military to dance to it on TikTok, “Hype Boy” celebrates youth culture and crushes with infectious charm. NewJeans member Hanni, then 17, co-wrote the lyrics, adding age-appropriate angst and authenticity. “Hype Boy” sounds fresh and modern, while also giving off a low-fi retro vibe. The five teenagers harmonize beautifully, but “Hype Boy” also showcases their individual voices in the barely three-minute song. Smoothly switching back and forth between Korean and English lyrics, NewJeans rev up when they hit the co-dependent giddy chorus: “’Cause I know what you like, boy/You’re my chemical, hype boy.” —Jae-Ha Kim

“I wanted to take a big risk,” Billie Joe Armstrong said, and this was it: a nine-minute, five-movement suite. They aimed for an emo “Bohemian Rhapsody” but delivered something more like glam-punk “Rockin’ in the Free World” for kids watching U.S. tanks roll through Baghdad on cable. The music is as ambitious as its message, with nods to their forebears, from Patti Smith to Ginger Baker to “Moonage Daydream,” served over big chords and crisp couplets. “I’ve walked this line a million and one fucking times,” Armstrong spits. And he never stopped. The band keeps re-aiming the charge for MAGA, Ukraine, Gaza. The angry-old-man song they swore they didn’t want to write is exactly what each new version of idiot America demands. —S.G.