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It all comes back to pop music. Pop is the backbone not only of the music industry, but of culture in general: Nothing else connects people, defines moments and lives and passes down history from generation to generation the way pop does. It’s our shared language, our communal experience. It’s why wedding receptions are usually joyous and celebratory occasions even if the DJ doesn’t know a thing about the people they’re playing to, why karaoke can feel like a spiritual awakening in the right circumstances, why top 40 and oldies radio remain cultural staples a decade into the streaming era. There is no safer bet, no easier sell than pop music.

And yet, there’s been relatively little attempt to properly canonize modern pop’s greatest works and practitioners. While rock as a genre has been listed and anthologized to death over the past 50 years, and hip-hop and country are finally starting to catch up, such pop histories are relatively few and far between. There’s no official pop hall of fame, like there is for those other genres. It shouldn’t be possible for the biggest music on the planet to be overlooked, but it does feel that way sometimes.

So we here at Billboard have decided to take the occasion of the 65th anniversary of the Billboard Hot 100 — with the chart finally having lived a full-enough life to be at retirement age, though it’s still as vital as ever and certainly nowhere near hanging it up — to take our shot at listing the 500 best pop songs since the chart’s debut. Though songs had to hail from the Hot 100 era to qualify for our list, this isn’t a charts-determined ranking: Rather, these are the songs our staff felt were simply the greatest, most enduring pop songs of that 65-year period, the songs that we most think of when we think of what pop music could and should be. (Because 500 is a much smaller number than you think when talking about 65 years of pop music, and because we wanted to be able to include as many different artists as possible, we capped the number of pop songs per lead artist at three.)

How are we defining “pop songs,” you might ask? Well, that’s a little tough: One of the reasons pop can be hard to summarize is because there’s no real sonic or musical definition to it. There are common elements to a lot of the biggest pop songs, but at the end of the day, “pop” means “popular” first and foremost, and just about any song that becomes popular enough — whether it be rock, dance, rap, R&B, country, reggaetón or some combination — can be considered a pop song. So the only hard-and-fast qualification we laid down for songs to be eligible for our list was that they had to have hit the Hot 100 at some point, in some version. (The only exception we made was for songs that came during the ’90s period where many huge airplay hits were ineligible for the Hot 100; read here for more details on that.)

All that said, the “pop” part of this project was still essential when determining our ranking. We were looking for the songs that most fit our idea of pop music — catchy, tight, rousing, emotional, immaculately crafted, instantly memorable. If a song didn’t strike us as an obvious pop song, we might have ranked it lower on our list than most other all-time songs lists have in the past, or left it off altogether. Conversely, if a song makes us go “now that’s a pop song!” every time we hear it, even if it’s not the kind of critically revered song that often ends up on all-time lists, we made sure to give it a little extra love here. Our definition of pop might differ from yours — we couldn’t even all agree on every song ourselves — but even if we can’t do much better than “we know it when we hear it,” we’re confident you’ll hear it plenty yourself while reading through the songs on our list.

Here are our staff’s 500 favorite pop songs since the introduction of the Billboard Hot 100 on Aug. 4th, 1958 — from Lesley Gore to Carly Rae Jepsen, from Sam Cooke to SZA, from The Kinks to The Chainsmokers, from Chubby Checker to Rae Sremmurd. We’ll be counting down from 500 to 301 today (Oct. 17), then from 300 to 101 on Wednesday, with the final 100 being unveiled on Thursday (Oct. 19), along with more related articles you can read all about here.

Join us below all week, and feel free to sing along; we know you know the words.

500. Los Del Rio, “Macarena (Bayside Boys Mix)”

Image Credit: Evan Agostini/Liaison/Getty Images

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There are a million reasons why a musical artist catches lightning and sends a song to the top of the charts: Maybe they’re a superstar with a bulletproof commercial offering, or they’re an unknown riding cultural headwinds to a strong reaction, or they’re somewhere in between, with the right TikTok challenge at the right time. Sometimes, though, they’re just that good — commandingly, undeniably good — with a song that showcases that talent.

That’s how it felt in January 2021, when the co-star of High School Musical: The Musical: The Series released her debut single.

With the still-dazzling “Drivers License,” Olivia Rodrigo arrived as a fully formed pop savant, capable of piercing turns of phrase, major-key choruses and bridges that stop you in your tracks and force you to sway along. Of course her debut album, 2021’s Sour, was just as impressively detailed and sumptuously catchy; of course songs like “good 4 u” and “Deja Vu” became just as ubiquitous on top 40 radio and streaming services; of course the best new artist Grammy was in the bag; of course the first headlining shows were giddy shout-alongs. With a preternatural talent like Rodrigo, the artistic and commercial successes felt predestined from the moment we first heard, “‘Cause you said forever, now I drive alone past your street.”

With Guts, Rodrigo’s feverishly anticipated sophomore album, the rocket ship keeps climbing higher and higher: if Sour represented a rock-solid, no-skips debut, its follow-up is a bigger and better sequel, more confident and gripping in almost every way. The personal stakes are higher as Rodrigo gestures at the life changes (and expectations) that her newfound stardom have produced, but she matches them by thrusting her songwriting into more adventurous, and rewarding, territory.

Rodrigo expands upon the heartbreak central to Sour on songs like “Logical” and “Love Is Embarrassing,” but also addresses fame leeches (“Vampire”), social awkwardness (“Ballad of a Homeschooled Girl”), body image standards (“Pretty Isn’t Pretty”) and pre-adulthood anxieties (“Teenage Dream”), among other topics. Just like he did on Sour, Dan Nigro, Rodrigo’s main studio collaborator, helps push the right buttons while getting out of the way of her towering songwriting, as the pair hopscotch through pop-punk, new wave, indie-folk and hushed balladry without sounding haphazardly constructed or dulling any one-liners.

Because that’s what stands out the most on the first few listens of Guts: the way Rodrigo can bring a lyric to life with a gut-punch metaphor or a pitch-perfect vocal delivery. That gift stood out on Sour, and has sharpened on its follow-up. “I am built like a mother, and a total machine/ I feel for your every little issue, I know just what you mean,” she sings on opener “All-American B–ch,” crystallizing the impossibility of Relatable Female Pop Stardom in one lilting rhyme. On “The Grudge.,” Rodrigo flattens a breakup into, “We both drew blood, but man, those cuts were never equal.” And on “Making the Bed,” Rodrigo distills the ephemeral nature of success: “Another perfect moment that doesn’t feel like mine/ Another thing I forced to be a sign.” Guts has plenty of potential singles to join the already-minted Billboard Hot 100 top 10 hits “Vampire” and “Bad Idea Right?,” but those lyrics — the ones that feel painfully perfect, that you want to write down for your own inspiration — are even more plentiful.

That remarkable songwriting ability is what ultimately separated Rodrigo when “Drivers License” launched, and what makes the sky her limit today. With Guts, Rodrigo has released the most complete pop album of the year, and nudged her trajectory even higher.

All 12 songs on the standard edition of the album are top-notch, but which are the early standouts? Here is a preliminary ranking of every song on Olivia Rodrigo’s Guts.

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