The 500 Greatest Songs of All Time

The lead single from Harry Styles’ third album balances its agitated inner monologue, where the shape-shifting pop star picks at the details of a relationship in crisis, with spun-sugar synths that give cover to his torment. From its playful opening — Styles’ goddaughter Ruby giggling “Go on, Harry, we want to say goodnight to you!” — to its singsong bridge, during which Styles’ thoughts are ping-ponging around his head at “high-speed internet” velocities, “As It Was” paints an unusually vivid picture. Everything might seem fine on first glance, but it all becomes more troubling (“What kind of pills are you on?”) with each repeated glimpse.

An epic story-song about a bandit and the friend who betrays him, “Pancho and Lefty” became a country hit thanks to Willie Nelson and Merle Haggard’s 1983 duet. But it’s the songwriter’s own forlorn reading, on 1972’s The Late Great Townes Van Zandt, that best conveys the doomed fates of the main characters. It begins with what might be one of the most descriptive opening verses in the country-folk canon: “Living on the road my friend/was gonna keep you free and clean/now you wear your skin like iron/your breath as hard as kerosene.” “It’s hard to take credit for the writing,” Van Zandt said in 1984, “because it came from out of the blue.”

“That song is my life and its words are my truth,” Lizzo wrote at the time. She had to tack on a writing credit to British singer Mina Lioness, who had tweeted its iconic line “I just took a DNA test, turns out I’m 100 percent that bitch,” but the power of this gale-force breakup banger was pure Lizzo, uproariously swaggering and endearingly soulful. “Truth Hurts” was originally released in 2017, but the song got a big boost two years later, when Gina Rodriguez day-drunkenly sang it in the Netflix show Someone Great, and it became Lizzo’s signature hit.

“We did it because my career was on the wane and we wanted something to make a hit,” Harry Nilsson bluntly told an interviewer when asked why he covered Badfinger’s near-despondent ballad: “I heard it and searched through every Beatles album for two and a half weeks, trying to find out which one of their tunes it was.” Producer Richard Perry agreed, piling on the strings to showcase Nilsson’s desperate lunge of a vocal. Both were right — the song went to Number One and earned a Grammy nomination for Record of the Year.

The holy mother of all diss tracks, “You’re So Vain” contains one of the most enduring musical mysteries of all time. Just who is so vain that he probably thinks the song is about him? Simon previously revealed that actor Warren Beatty inspired the second verse of the song (“Oh, you had me several years ago/When I was still naive”), but speculation abounds regarding the other man (or men) behind the ire. Either way, the track — boasting omnipresent Seventies arranger Paul Buckmaster’s orchestration and Mick Jagger’s background vocals — is pure soft-rock fire.

Cyndi Lauper was nervous about “Time After Time” — the aching ballad she wrote in the studio with keyboardist Rob Hyman to finish off her blockbuster solo debut, She’s So Unusual. “I asked them to please not put ‘Time After Time’ out as the first single,” Lauper said. “People would never have accepted me. If you do a ballad first, and then a rocker, that doesn’t work.” Her instincts were right: Following the jaunty “Girls Just Want to Have Fun,” “Time” became her first Number One.

No song typifies the freakish pop instincts that made the Pixies stand out in a sea of gloomy Reagan-era bands better than “Where Is My Mind?” Joey Santiago’s lead guitar is catchier than most Top 40 hooks, and by the time Fight Club made this song iconic a decade after its release, it had already formed part of the DNA of countless alternative-radio hits in the years between, from Nirvana to Korn. When an interviewer in 1988 asked about his unique ability to crank out great songs, Black Francis’ answer was typically cryptic: “It’s nice to have space. How much can one brain deal with?”

Explaining the tighter, broader-reaching songs on his third album, Graduation, Kanye West said, “I applied a lot of the things I learned on tour [in 2006] with U2 and the Rolling Stones, about songs that rock stadiums. And they worked!” West found the inspiration for his most grandiose statement to date from Daft Punk’s “Harder, Better, Faster, Stronger,” which he sampled and reshaped. West is a big fan of the French duo: “These guys really stick with the whole not-showing-their-faces thing. Just amazing discipline — that’s straight martial-arts status.”

It’s likely that no song on this list has soundtracked more dinner parties than Kind of Blue’s warm, welcoming first track. But at the time it was a jarring departure, trading bebop chord changes for a more open-ended modal style. According to pianist Bill Evans, the trumpeter worked up his material just hours before recording dates, but the all-star band here sounds like it’s been living with “So What” for years: Saxophonists John Coltrane and Cannonball Adderley turn in solos that have since become as iconic as any in jazz history, and the rhythm section of Evans, bassist Paul Chambers, and drummer Jimmy Cobb swings like it’s dancing on air.

“Tití Me Preguntó” is a showcase for Puerto Rican superstar Bad Bunny’s unbridled creativity and eccentric pop genius, mixing frantic dembow beats, a classy sample by bachata master Anthony Santos, and a coda with a dash of Latin psychedelia to the global mainstream. He does it all with panache and a healthy sense of humor. Using the archetype of the concerned Latin American aunt asking about her nephew’s potential girlfriends as a starting point, he launches into a hilarious tirade of salacious puns to a bouncy party vibe that — in typical Bad Bunny fashion — unexpectedly morphs into moody self-reflection.

Montero Hill was an Atlanta college dropout sleeping on his sister’s couch and looking to break into music when he came across a track he liked by a Dutch 19-year-old called YoungKio that was based around a banjo sample from a Nine Inch Nails track. “I was picturing, like, a loner cowboy runaway,” he told Rolling Stone. Within a year “Old Town Road” was the longest-running Number One song of all time, seeming to sum up eons of American cross-cultural love and theft in just one minute and 53 seconds.

Notified by fax that her services in the Pixies were no longer required, Kim Deal called up her twin sister, Kelley, to be her new guitarist (never mind that she didn’t know how to play guitar) and had the last laugh when this absurdist gem became an MTV phenomenon in 1993. “When people were talking about the Breeders being a one-off,” Kelley told Rolling Stone, “I was like ‘No, actually … the Pixies are a side project.'” A little over a year later, the Breeders were on an extended break of their own, but the effortlessly fun trampoline bounce of “Cannonball” is one for all time.