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The 250 Greatest Songs of the 21st Century So Far

25 years of classic hits from all over the musical map and every corner of the globe

250 greatest songs of the 21st century so far illustration

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If there’s anything that defines music in the 21st century, it’s constant change. We live in an era when your next favorite song could come from anywhere — all over the stylistic map, all over the world.  The whole experience of being a music fan keeps mutating all of the time. Back in Y2K, when ‘NSync dropped “Bye Bye Bye,” it was the peak for the era of buying CDs, until that era went bye-bye-bye. Napster happened; so did MySpace and the iPod. Streaming arrived; vinyl came back. New sounds keep getting invented, with the air full of eclectic and experimental songs. If you’re a music fan these days, you’ve got a whole planet of sound at your fingertips.

That’s the spirit behind our list of the 21st century’s 250 greatest songs so far. Like our list of the century’s greatest albums, it’s a wide-ranging mix of different styles, different beats, different voices. Some of these songs are universally beloved hits; others are influential cult classics. But this list sets out to capture the full chaotic glory of 21st-century music, one song at a time.

These tunes come from all over the map. In our Top Ten alone, we go from Stockholm to Compton, from Nashville’s Music Row to New York’s sleazy punk-rock bars. These songs range from Seoul to Spain to San Juan, from Vegas to Veracruz to Versailles, from Nigeria to Mexico to Colombia. There’s reggaeton and K-pop and drill and crunk, country and Afrobeats and emo and sirrieño. But the criterion for this list isn’t popularity or airplay — strictly musical brilliance and originality. Wherever these songs come from, they remind you that we’re living in a time of wide-open possibilities and nonstop innovation. Some of the most famous megastars of our moment — Beyoncé, Taylor Swift, Kendrick Lamar — are also the most adventurous.

Some of these songs come from legendary artists who managed to stay vital across the decades, like David Bowie, Mary J. Blige, Madonna, or Bob Dylan. Others come from teenage dirtbags. We have “Anthems for a 17-Year-Old Girl”; we also have “Drivers License,” an anthem from a 17-year-old girl. We have the ancient country grit of Johnny Cash, who signed off the year Olivia Rodrigo was born. We’ve got one-hit wonders, plus entire genres that came and went overnight. (Take a bow, Christian nu metal.) There’s tortured poetry and raw confessions. There’s also the one that goes, “Baby, you a song.”

We had plenty of arguments while putting this list together — and we enjoyed every minute. It’s a list of songs, not artists, so we mostly avoided repeating multiple tunes by the same performer. But some musical masterminds just had too many classics to deny. (If the universe wants to give Lorde both “Ribs” and “Green Light” in the same career, you can’t tell it not to.) Every fan would compile a different list — that’s the point. But this list sums up an era when there are no rules to follow, no playbooks to obey. Nobody made this list by playing it safe. Read on, turn up the music, explore — and get ur freak on.

You can listen to the whole list here, and to hear an in-depth interview with Missy Elliott about the making of our top pick, 2001’s “Get Ur Freak On,” go here for the podcast provider of your choice, listen on Apple Podcasts or Spotify, or just press play above.

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From Rolling Stone US

250

Train, ‘Drops of Jupiter’

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

249

Tweet, ‘Oops (Oh My)’

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

248

Fleet Foxes, ‘Tiger Mountain Peasant Song’

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

247

Avicii, ‘Levels’

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