Rolling Stone Greatest Songs

Rolling Stone 500 Greatest Songs: Santana, ‘Oye Como Va’ (#479)

For virtually the entirety of his long career, Carlos Santana has defied expectation or easy categorization.  He’s generally lumped in among the guitar gods of the classic rock pantheon, occupying an eliptical orbit somewhere between Ritchie Blackmore, say, and Michael Schenker.  He doesn’t sound like Blackmore or Schenker, you understand — Carlos Santana doesn’t sound like anyone but Carlos Santana — but in terms of his influence, he’s somewhere in that territory.

You can kind of see how Santana wound up referenced where he is in the classic rock taxonomy.  He played at Woodstock, he employed a distinctive fuzzy guitar tone, and he lived in San Francisco during a time when that city served as the home base for a number of other artists who made a cultural impact:  Jefferson Airplane, Janis Joplin, the Grateful Dead.

But even a cursory listen to Abraxas — the 1970 album that featured ‘Oye Como Va’ and ‘Black Magic Woman’, Santana’s signature songs — derails the guitar god narrative.  Not because Carlos Santana is or was unworthy of inclusion among rock’s guitar greats, but more because his inclinations towards blues and Latin jazz took him so far afield from what any of his peers were doing.  Or to put it another way, Abraxas is a lot closer in sound and intent to something like Miles Davis’ Bitches Brew, which came out the same year and on the same label, than to anything Janis or Paul Kantner or Jerry Garcia were doing.  If not for Woodstock and the Bill Graham[1]Bill Graham, 1931 – 1991, was an influential concert promoter, roughly analogous to a movie producer. / San Francisco connection, it’s entirely possible we’d more accurately think of Carlos Santana as a Latinized fusion jazz musician instead of a guitarist on the classic rock periphery.

The first Latin jazz great Tito Puente knew that someone had covered his 1962 song ‘Oye Como Va’ was when his wife Margaret heard the song while she was out shopping.  She recognized the song as her husband’s, but with Greg Rollie’s funky-assed organ and Santana’s distorted guitar where the horns and the flute should have been.  Definitely not anything that Tito had ever recorded, though Santana’s version is unmistakably the same song.

Tito apparently wasn’t too thrilled at first to hear of some upstart West Coast rock outfit covering his song, but time and royalty checks — Tito was given sole writing credit on the album — changed his view, wiuth Puente himself acknowledging that Carlos Santana had “put our music around the world.”

Michael Strum: “For a man I usually think of as a paragon of guitar, it’s the organ and the bass line that really stand out to me on ‘Oye Como Va’. Tito Puente’s charm is preserved, adapted, and enhanced in Santana’s rendition. A classic, a groundbreaker for Latin music, and a welcome entry here as our first non-English song, the Kanye haters notwithstanding.”

Rolling Stone: Growing up in San Francisco, Carlos Santana was shaped by the city’s psychedelic explosion. “You cannot take LSD and not find your voice,” he once claimed, “because there is nowhere to hide.” And while his early heroes were bluesmen, he changed history with this foundational Latin-rock reworking of a 1962 salsa number by Cuban percussionist Tito Puente. Santana kept the original’s cha-cha pulse but replaced its horns with Greg Rolie’s organ and Carlos’ lysergic guitar flares. Said Puente years later, “He put our music, Latin rock, around the world, man.”


1 Bill Graham, 1931 – 1991, was an influential concert promoter, roughly analogous to a movie producer.
Rolling Stone Greatest Songs

Rolling Stone 500 Greatest Songs: Lil Nas X, ‘Old Town Road’ (#490)

The list of 500 Greatest Songs we’re working from was updated by Rolling Stone this very year, in 2021.  To this point in our progress, #500 through #490, the song selection spans 60 years.  Miles Davis’ ‘So What’ (#493), from 1959, is the oldest song, while this entry, ‘Old Town Road’ by Lil Nas X is the most recent, from 2019.

Over the course of these 60 years, we’ve seen fundamental paradigm shifts in popular music that have had profound effects not just on the way music is conceived and recorded, but also in the way that it’s distributed and received.

The first of these major shifts, of course, was video.  Music videos aren’t solely responsible for the performative visual aspects of pop music — people were mixing performance art with music long before video made the scene — but there’s no question that video has helped push the visual element to the forefront.  It’s the rare hit song released after 1982 that’s not associated with a professionally directed music video.  You don’t think of one without the other.  Try to imagine Michael Jackson’s ‘Thriller’, Nirvana’s ‘Smells Like Teen Spirit’, Britney Spears’ ‘Hit Me Baby One More Time’, or Eminem’s ‘The Real Slim Shady’ without their attendant videos.  The resulting pop firmament suddenly looks like a vastly different place.

The second major shift, the metaphoric earthquake that’s currently roiling the landscape, has been the advent of internet and social media:  Facebook, Twitter, YouTube, Tik Tok, Instagram, Vine, etc.  These tools have allowed savvy cybernauts and aggressive social networkers to create, market, and distribute their own material, cheaply and effectively.

That’s exactly what happened with Montrero Hill, a.k.a. Lil Nas X, a charismatic young internet personality who did a little of everything across various platforms and formats before buying an online sample of a Nine Inch Nails song for $30 and writing ‘Old Town Road’ around it.  He released the song in December 2018, and made online memes to promote it.  Users — lots of users, fucking tens of millions of users — took notice, and began making and sharing short-form videos with the song on Tik Tok.

Feeling old yet?

‘Old Town Road’ was popular enough to debut in the Billboard Hot 100 (eventually reaching #1, where it enjoyed a long tenure).  Billy Ray Cyrus heard it, and contributed to a new mix (the original version was less than two minutes in length).  Lil Nas X was signed to Colombia Records.

Before Cyrus’ involvement, the song also hit the country charts…and we’re not talking scraping the bottom of the country charts either.  It hit #19 country.  And then it was removed from those charts in March 2019 by Billboard, who issued this statement:

“Upon further review, it was determined that ‘Old Town Road’ by Lil Nas X does not currently merit inclusion on Billboard‘s country charts. When determining genres, a few factors are examined, but first and foremost is musical composition. While ‘Old Town Road’ incorporates references to country and cowboy imagery, it does not embrace enough elements of today’s country music to chart in its current version.”

Uh huh.

Let’s do this.  Call it the Yeehaw Challenge, Pt. 2.  Go listen to Bebe Rexha and Florida Georgia Line’s ‘Meant to Be’ — #3 on the country charts the week ‘Old Town Road’ was removed — then try identifying exactly which elements of today’s country music are being embraced in that song but are absent in ‘Old Town Road’.

We’ll wait.

Michael Strum: “‘Old Town Road’ makes me feel light, warm, all-encompassing joy. Who needs meth when you’ve got Lil Nas X? I love the timber of his voice, his flow, his accent (‘matt-ee!’), the mix. I love the boldness to mix genres. I love and am inspired by his Pride. I love seeing black input in country again, in the tradition of Ray Charles’ ‘Modern Sounds in Country Music’ (1962). Langston Hughes called out for us to Let America Be America, and Mr. Hill answers the bell ably: wake up on your sister’s couch, find a track, rap about a cowboy hat from Gucci, and break American pop music. That’s a rags to riches story that would make H. Alger blush! A rock and roll story and a great choice here.”

Rolling Stone: 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.

Rolling Stone Greatest Songs

Rolling Stone 500 Greatest Songs: Guns ‘n Roses, ‘Welcome to the Jungle’ (#491)

Oh my God.

Buried in the mix roughly seven seconds into ‘Welcome to the Jungle’, those are the first words we hear on Guns n’ Roses’ bleak and brilliant Appetite for Destruction.  A reflexive gasp of shock, horror, and moral revulsion, it serves as a kind of mission statement for the snarling catalog of human failure and near-unremitting darkness that follows.  Appetite is a Chandleresque vision of the City of Angels set to Hell’s own soundtrack: a victim-on-victim freakshow chock full to the brim with junkies, hustlers, porno hounds, and lost, lonely souls.

All five of the band’s members — singer W. Axl Rose, guitarists Slash and Izzy Stradlin, bassist Duff McKagan, and drummer Steven Adler — are credited as writers on ‘Jungle’, but the moral viewpoint is that of Rose and Stradlin, Indiana natives and boyhood friends.  You can take the boys out of the Midwest, apparently, but taking the Midwest out of the boys might be another task altogether.  You get the sense that Hollywood, CA might’ve come as something of a shock after Lafayette, IN (though both Rose and Stradlin had lived in LA for years by the time ‘Jungle’ was written).

That the album even has a viewpoint, moral or otherwise, is the first of many qualities that sets Appetite apart.  The popular hard rock of the era, largely dictated by music videos, was characterized by a sort of slummer’s glam:  big hair, gaudy outfits, and bloated, radio-friendly production.  Art, even by the lax standards of pop music, took a back-seat to image.

The same year Appetite came out, 1987, saw releases by popular hard rock acts like Def Leppard, Motley Crue, Faster Pussycat, and Whitesnake…and compared to those offerings, Appetite might as well have been conceived and recorded in some alternate dimension.  Whatever excesses GnR’s contemporaries might have been getting up to off-stage, their actual output — both visual and sonic — was safe and inoffensive as mother’s milk, and shallow as a kiddie pool.  Music that had the pretense of social insurrection with little of its bite and none of its cost.

And then, suddenly, there was ‘Welcome to the Jungle.’

Saying it was startling doesn’t do it justice.  It was lean and mean, nasty and exhilarating and even a little scary.  There was nothing remotely polite or appropriate about it.  (Seriously, it doesn’t matter what volume you listen to ‘Jungle’ on; it always sounds loud.  It’s a song that means business.)  Even the way the band looked — toxic and unhealthy, cloaked in a grimy venereal sheen — was different.  Balanced against the pabulum you were used to, it was a little like getting splashed with a bracing faceful of cold gasoline…

….and then being lit the fuck on fire.

Michael Strum: “‘Welcome to the Jungle’ sounds like five young, musically-inclined, adrenaline-ridden white guys trying to write a theme song for Roach, the echo-locating grenadier at the Do Long bridge in ‘Apocalypse Now’. Unformed, undifferentiated wildness permeates, providing uneasy energy. Another sticky title here, perhaps a victim of its own success as a cultural touchstone now crossed over into hackneyed trope. Creeping determinism, or hindsight bias, remind us to appreciate the creativity present in ‘Jungle’, to recall the world before it existed and became iconic and played out. The perceived inevitability lies not in a lack of creativity by GnR, but in ourselves, dear Brutus, in another of our all-too-human cognitive errors. The internet was right about how to enjoy ‘Welcome to the Jungle’; ignore the singing and focus on the eclectically-influenced musical construction, and good things await.”

Rolling Stone: Released as the first single from Appetite for Destruction, “Welcome to the Jungle” stiffed at first — it took the massive crossover success of “Sweet Child o’ Mine” to ready radio for GN’R at their most unvarnished. The song’s inspiration, according to Axl Rose, was a hitchhiking trip that landed him in the Bronx, where a stranger approached him and said, “You know were you are? You’re gonna die, you’re in the jungle, baby!” Rose took this mockery and turned it into an anthem.

Rolling Stone Greatest Songs

Rolling Stone 500 Greatest Songs: Miles Davis, ‘So What’ (#492)

Miles Davis’ Kind of Blue, the album from which ‘So What’ is taken, is perhaps the best selling jazz album of all time.  If you’ve only ever heard one or two jazz songs in your life, chances are good that one of them is ‘So What’ (and the other one is probably ‘Take Five’ by Dave Brubeck).  As of 2019, Kind of Blue had sold over five million copies, making it one of the very few instances in your lifetime of a conspicuous overlap between high art and popular culture.

And make no mistake, when we invoke art in connection with what the Miles Davis Quintet are doing on Kind of Blue…?  We’re talking Art with a capital ‘A’.  Ars gratia artis:  pushing the envelope of what has and can be done, delivering a type of music from embryonic conception into full-blown reality.

A composer and musical theorist named George Russell developed what he called the ‘Lydian Chromatic Concept of Tonal Organization’ in 1953.  Each of the songs on Kind of Blue (1959) and its predecessor Milestones (1958) are an experiment, more or less, in Russell’s theory of modality:

The term ‘modal jazz’ refers to improvisational music that is organized in a scalar (‘horizontal’) way rather than in a chordal (‘vertical’) manner. By de-emphasizing the role of chords, a modal approach forces the improviser to create interest by other means: melody, rhythm, timbre, and emotion. A modal piece will generally use chords, but the chords will be more or less derived from the prevailing mode.” — Peter Spitzer, ‘Modal Jazz

Did you catch all that?  That’s the simple version.

No disrespect to any of the other entrants, but discovering Davis and his Kind of Blue collaborators on this Rolling Stone list — shoe-horned in among modern hip-hoppers, 80’s pop stars, and 70’s soft rock icons — is a little like attending a middle school science fair and finding a working cold fusion engine amidst the volcano, tidal wave, and dinosaur bone exhibits.

Why has Kind of Blue and ‘So What’ endured over the decades as both entry point for neophytes and accepted classic for connoisseurs?

Well, for starters, the members of the Miles Davis Quintet that you’re hearing were literally some of the best musicians on the planet.[1]And if any of them were alive today, they’d still be perhaps the best musicians on the planet.  Miles Davis (trumpet), John Coltrane (tenor saxophone), Cannonball Adderley (alto saxophone), Bill Evans (piano), Paul Chambers (bass), and Jimmy Cobb (drums)…if they were a sports team, they’d all be first ballot Hall of Famers.  Each and every one of them looms large in the history of jazz and American music.

In addition to all that, ‘So What’ is just insanely, other-worldly cool.  As cool as cool gets.  Cool as the other side of the pillow.  So cool that you can’t help but cover yourself with some of its coolness just by proximity to it (seriously, playing it will bolster your self-esteem and increase your prestige in the eyes of your fellow man).  You don’t need to know anything about jazz or music theory to fall under its intricate, atmospheric spell.  It’s music for Real People.™

Michael Strum: “Suffice it to say, Miles Davis was a giant. ‘So What’ is a perfect introduction to his canon, with all its grandeur. The balance, the construction, the consumate technial skill, the obvious love. The track plays on like the scale of the Himalayas; just when your eye thinks you’re done, you see another ridge and valley beyond, ’til you can’t fathom what your eyes are reporting. Such is what Miles Davis gives the ears. One doesn’t have to like peanuts or care about agricultural science to appreciate George Washington Carver; so it is with jazz and Miles Davis. Some genius is so great as to require only the slightest scrap of humanity to see it; we are all better for it.”

Rolling Stone: 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.


1 And if any of them were alive today, they’d still be perhaps the best musicians on the planet.
Rolling Stone Greatest Songs

Rolling Stone 500 Greatest Songs: The Pixies, ‘Where Is My Mind’ (#493)

Mix two parts talent, two parts blind faith self-actualization, and one part stumbling ass-backwards into the loving arms of destiny, and you’d wind up, maybe, with something like the Pixies.

Or homeless.  There’s a good chance you’d wind up homeless.

Band founders Charles Thompson, a.k.a. the once and future Black Francis, and Joey Santiago, make each other’s acquaintance in the mid-80’s when they wind up sharing dorm space at the University of Massachusetts, Amherst.  Technically speaking, they’re not there for music.  Thompson is studying anthropology, and Santiago is an economics major.  Whatever.  The two recognize some mutual interests and begin dipping their toes in the songwriting pool.

Halfway through the Amherst experience, Thompson takes off for Puerto Rico to study Spanish, returning six months later to drop out of college.  He persuades Santiago to drop out as well, and the two “form a band” in Boston in 1986, with Santiago handling guitar and Thompson on vocals.

They place an ad in a local music paper for a bassist who likes Husker Du and Peter, Paul, and Mary, which is a little like asking for someone who enjoys both Slayer and the more rambunctious works of Joan Baez.  The only person who answers the ad is a woman named Kim Deal.  She doesn’t play bass, has never played bass.  She doesn’t even have a bass.  You get where this is going, right?  She’s hired.

Ms. Deal’s husband recommends a drummer, David Lovering, and the line-up is complete.  The band chooses a name at random from the dictionary — the Pixies! — while Charles Thompson gives himself an alias, Black Francis, and they’re off, playing shows in and around the Boston area.  It’s VH1 Behind the Music shit on steroids.

Fast forward a couple years, and The Pixies put out a full-length LP, Surfer Rosa, which features ‘Where Is My Mind?’  The album’s an aggressive combination of loud, obnoxious, and awesome, like The Replacements, Sonic Youth, and Dinosaur Jr. (another band with roots in Amherst) blended their fucked up DNA in some unholy caldron and cranked the dial up to eleven, Spinal Tap style.  The sound on Surfer Rosa would heavily influence Kurt Cobain and Nirvana, with its alternating loud / quiet dynamics.  The producer of Surfer Rosa, Black Flag’s Steve Albini, would produce Nirvana’s last album, In Utero.

What jumps out about ‘Where Is My Mind?’ — a song about, um…fish? — is how ahead of its time it sounds.  Or how timeless it sounds.  Or something. It doesn’t really have any peers, by virtue of there not being anything else that sounds quite like it. It’s huge, loud, unforgettable, just this side of unhinged.  A howling, megasonic mic drop of a song, one that’s still as powerful and startling as the day it was recorded.  It was never released as a single, because how the fuck could it be?  It was featured at the end of David Fincher’s Fight Club, though, and that’s almost the same thing.

Michael Strum: “This is brilliant. Builds nicely. There’s a phonographic architecture that unfolds and unevils itself skillfully: acoustic guitar building and then the electric guitar joining in with characteristic distortion. Sounds almost discordant but intentionally so, something a friend of mine has said about the Rolling Stones. That degree of looseness is a sign of real musical talent across the group. A good friend of mine who is a Pixies fan doesn’t like this song, which reminds them of ‘Uptown Girl’ or ‘Touch of Grey’ by the Grateful Dead, which seem to be universally reviled by the dedicated aficionado. Like many great songs, ‘WIMM?’ transports the listener to a specific time and place.”

Rolling Stone: 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?”

Rolling Stone Greatest Songs

Rolling Stone 500 Greatest Songs: Cyndi Lauper, ‘Time After Time’ (#494)

A culture’s hit songs are the hotline to its memory; enduring mile markers on our collective life’s road.  They’re both reflective and representative of the time and circumstance in which they were made.

Cyndi Lauper’s ‘Time After Time’ was released as her second single in February 1984, from her debut album, She’s So Unusual.  The song hit #1 in the US the second week of June 1984.  Nine of the songs, including Lauper’s, that were in that week’s Top Ten had videos that were in moderate to heavy rotation on MTV.[1]For the record, in addition to Lauper at #1, those songs were:  2. Deniece Williams, ‘Let’s Hear It for the Boy’; 3. Steve Perry, ‘Oh Sherrie’; 4. Duran Duran, … Continue reading    Let’s allow that videos weren’t necessarily the sole or primary reason these songs were in the Top Ten; we might just as well say the videos saw heavy rotation because the songs were in the Top Ten.

But still…those videos most definitely had some effect.

The early 80’s were the crest of a media tidal wave that in some ways is still rolling inland.  FM radio overtook listener market share in the late 70’s, and by 1982 was commanding 70% of listeners.  The first US Sony Walkman was introduced in 1980.  Cassettes would overtake vinyl as a preferred format in the mid-80’s, and be themselves overtaken less than ten years later by CD’s.

MTV made its debut in August 1981.

Over time, video would change the game, altering not only how music would be created and consumed (and in some cases, who would do the creating and consuming), but also — germane to our purposes — how it would be remembered.

Where Cyndi Lauper fits in amidst all this talk of memory and perception is that she’s so representative, both sonically and visually, of the very particular time and circumstance in which ‘Time After Time’ was recorded and performed.  She was one of the first real stars of the video era, and as such is both defining and defined by her specific time in music history.

Now make no mistake:  Cyndi Lauper could really sing.  This was no auto-tuned dancer propped up by slick production and crack marketing.  Lauper had a powerful voice with a wide range, and was singing and performing professionally long before She’s So Unusual ever saw the light of day.

That voice was used to marvelous effect on ‘Time After Time’.  Written by Lauper and the Hooters’ Rob Hyman, ‘Time’ is one of pop’s great good-bye songs, achingly sad, in which love fails to conquer all.  Its heavy synth and bright guitars notwithstanding, it’s a structurally spare and sure-footed song.  The secret sauce here is Lauper herself, honest and unadorned.  She spends most of the song sounding like she’s choking back tears, and restrains herself for everything but the crucial payoff point in the chorus (“I will be waiting!”). 

Be warned:  that chorus is likely to elicit a tear or two from the unwary.

Michael Strum: “What makes something ‘good’? The greatness of ‘The Shawshank Redemption’ (1994) is indubitable, but what of ‘Airplane’ (1980)? Can a cheeseburger be great What about a fast food one? I’m of the school that something can be good—or even great—without fanciness or even significant complexity. What we get from Lauper is a beautifully-constructed pop song, with nice execution to boot. A definitive ‘80s sound to my ear. I find sublime beauty and grace in Ken Griffey Jr’s swing, even if it’s not ‘The Nutcracker’. I marvel at a NY strip from Ruth’s Chris (the two times that I’ve had one, anyway), but I also revere Five Guy’s cheeseburger (double, extra cheese). ‘Time After Time’ is perfectly brilliant at being what it is, and that’s enough for me at 494.”

Rolling Stone: 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.


1 For the record, in addition to Lauper at #1, those songs were:  2. Deniece Williams, ‘Let’s Hear It for the Boy’; 3. Steve Perry, ‘Oh Sherrie’; 4. Duran Duran, ‘The Reflex’; 5. Night Ranger, ‘Sister Christian’; 6. Huey Lewis & the News, ‘The Heart of Rock ‘n Roll’; 7. Lionel Richie, ‘Hello’; 8. Irene Cara, ‘Breakdance’; 9. Laura Branigan, ‘Self Control’; and 10. The Pointer Sisters, ‘Jump (For My Love)’.
Rolling Stone Greatest Songs

Rolling Stone 500 Greatest Songs: Carly Simon, ‘You’re So Vain’ (#495)

On its surface, Carly Simon’s ‘You’re So Vain’ is a clever and gently scathing reproof of an affluent, maybe famous — and certainly famously — self-absorbed former lover:

You’re so vain
You probably think this song is about you

The hook?

It’s widely assumed that the song’s not about just any affluent, famous, and self-absorbed person, but a specific, real-life affluent, famous, and self-absorbed person (Warren Beatty[1]Ms. Simon has said the second verse really is about Mr. Beatty, but that he thinks the rest of the song is about him too.  Amusingly, he agrees, and has said so publicly. and Mick Jagger are the usual suspects).  This assumption has been nursed along with great care by Ms. Simon herself for near five decades now.  She’s doled out conspiratorial hints and winking asides at irregular intervals to various people, and of course none of these clues have ever led to anyone or anything.

All this mystery has resulted in ‘You’re So Vain’ being one of pop music’s most scrutinized songs, pored over and relentlessly scoured for all trace of meaning.

The irony here is that the song was probably never really about any one specific person, nor did it need to be.  It works just fine as an evocation of a type of person.  The enduring mystery over the ostensible subject(s) of ‘You’re So Vain’ may have successfully worn its way into the public imagination, but it’s perhaps done so at the expense of the song’s actual charms.

What all the marketing and conspiracy helped obscure is how clever and sharply observed ‘You’re So Vain’ really is.  Yes, this is a song about a woman putting some egocentric asshole on well-deserved retro-blast…but its disdain is mixed with amusement and regret and genuine loss:

You had me several years ago
When I was still quite naive
When you said that we made such a pretty pair
And that you would never leave
But you gave away the things you loved
And one of them was me

Collectively speaking, we don’t tend to think of Carly Simon as a song-writing heavyweight, but there’s not a line in ‘You’re So Vain’ that doesn’t hit its mark with devastating accuracy (including that bit-of-genius fourth wall-breaking chorus).  How many acknowledged song-writing heavyweights could say that about anything they ever wrote?

And we haven’t even mentioned Carly Simon playing her own piano on the tune, or that sinister opening bass line by Klaus Voorman[2]The same Klaus Voorman who played bass on our previous entry, Harry Nilsson’s ‘Without You’! (“Son of a gun…!”), or Mick Jagger’s uncredited backup vocals, or the snarky, fuck-you strings that make their appearance in the midst of the third chorus.

Well, I hear you went up to Saratoga
And your horse naturally won
Then you flew your Learjet up to Nova Scotia
To see the total eclipse of the sun
You’re where you should be all the time
And when you’re not, you’re with
Some underworld spy or the wife of a close friend…


Michael Strum: “I’m not a Jungian disciple by any means, though the pan-cultural success of a Mona Lisa or a Starry Night seems to suggest something of a ‘collective consciousness.’ I think ‘You’re So Vain’ is a cultural touchstone, though I suspect many — if not most — couldn’t ID Simon. There’s a notion from the medical improvement science field that’s germane here —borrowed directly from marketing, I believe — called ‘stickiness.’ The idea is that some ideas are ‘stickier’ than others, more memorable, more shareable, more ‘viral.’ There’s something in ‘You’re So Vain’ that’s remarkably memorable, a combination of sound and lyrics. It’s a powerful song that leaves an impression; it’s almost like…it’s about me? At any rate, C. Simon is an interesting woman with an impressive career. A survivor of childhood sexual abuse, she sets a wonderful example of resiliency and strength. She’s a better musician and songwriter than I gave her credit for, and I’m quite pleased with her presence here!

Rolling Stone: 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.


1 Ms. Simon has said the second verse really is about Mr. Beatty, but that he thinks the rest of the song is about him too.  Amusingly, he agrees, and has said so publicly.
2 The same Klaus Voorman who played bass on our previous entry, Harry Nilsson’s ‘Without You’!
Rolling Stone Greatest Songs

Rolling Stone 500 Greatest Songs: Harry Nilsson, ‘Without You’ (#496)

It wouldn’t be right to say that Harry Nilsson was accidentally famous.  He wasn’t just standing around, doing nothing, when John Lennon and Paul McCartney singled him out as their favorite American artist.  There’s a reason a pair of Beatles knew who Nilsson was.  Still, if ever a guy was accidentally famous in the days before social media and viral videos made accidental fame a common if toxic prospect, then Harry Nilsson was that guy.

Born in Brooklyn in 1941, Nilsson’s father abandons the family while the war’s still on.  By the time he’s fifteen, Nilsson is out in Los Angeles, working at the Paramount Theater and rubbing shoulders with musical types.  Following the theater’s closure in 1960, he finds work at a bank, where he lies about his non-existent high school diploma.  Armed with his work ethic and his ninth-grade education, Nilsson’s day job is programming computers for the bank, which ought to give you some idea of how bright Harry Nilsson was.  (The bank let Nilsson stay on in his job even after they discovered his deception.)

Harry keeps the bank job for most of the 60’s, and sings demos and sells songs on the side.  He signs with RCA as a recording artist in 1966, and in 1967 releases an album, Pandemonium Shadow Show.  One of the songs on that album was a funky-assed cover of the Beatles’ ‘You Can’t Do That’.  The Beatles’ press officer winds up buying an entire box of copies of the album, and at least one of those copies falls into the hands of John Lennon and Paul McCartney, who name-drop Nilsson during a 1968 press conference.  Before Nilsson knows it, the phone is ringing off the hook at his RCA office (he doesn’t have a manager, so he winds up answering the phone himself) and he’s hobnobbing with the Beatles in London.

Between the bank job and the release of ‘Without You’ (written by Badfinger members Pete Ham and Tom Evans) on his most successful album, Nilsson Schmilsson, Harry Nilsson had a song featured in 1969’s Best Picture winner, Midnight Cowboy; released an album of Randy Newman covers years before most people had ever heard of Randy Newman; and released an album of music he’d written and performed for an animated TV show.

Weird signposts on a weird road.

Harry Nilsson was often cerebral and could be somewhat gimmicky, but that’s not the case here.  What puts ‘Without You’ on the map — what makes it worthy of inclusion on a list like this — is that there’s no distance between singer and song.  Nilsson sings the absolute shit out of it, like his life depends on getting the point across.  He soars and pleads, nothing held back.  He’s not above or too cool for the material, nor does he make any attempt to disguise or diminish its overt sentimentality.  Instead, Harry Nilsson channels his inner Roy Orbison and just fucking goes for it, pressing the pedal all the way to the floor and keeping it there.

And that’s how you land a song on the Rolling Stone Top 500.

Michael Strum: “I don’t know why this song is here. It’s…fine. I don’t detect greatness here; this sounds to me like hundreds of other heartbroken love songs. While not my particular cup of tea — too low energy, though I like the piano — this Nilsson character seems like a cool dude. Having the Beatles name you as their favorite American act in a 1968 interview is a considerable feather in the cap. I’m warming to his inclusion here the more I learn of him, in a Lifetime Achievement manner. Let’s check the calendar: 1971 for Mr. Nilsson. I have a theory that 1968 – 1872 is the greatest five-year period in modern music, with 1972 the absolute acme. With a peek ahead, half of the songs so far are from 1971 or 1972. I expect this vein of phonographic gold to continue producing.”

Rolling Stone: “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.

Rolling Stone Greatest Songs

Rolling Stone 500 Greatest Songs: Lizzo, ‘Truth Hurts’ (#497)

Cheeky, sly, and irrepressible, Melissa Jefferson, a.k.a. Lizzo, wastes no time in getting right to it in ‘Truth Hurts’:

Why men great ’til they gotta be great?

We’d be hard pressed indeed to find a grown woman from a western-style democracy who hasn’t pondered that very question at some length.  And where Kanye West’s ‘Stronger’ allows no room for anyone who isn’t themselves an ultra-wealthy celebrity named Kanye, the experience Lizzo speaks to here is near-universal.  Granted, the specific details are hers — probably not a lot of women have a new thing going with a Minnesota Viking — but the general circumstances?  Picking oneself up and dusting oneself off following yet another disappointing affair with the kind of disappointing, dishonest asshole your friends all warned you about?  What woman hasn’t experienced some version of that?

There’s a strong element of personal empowerment that runs through Lizzo’s work, as if she’s been radicalized by a lifetime’s worth of exposure to shitty men and petty nonsense designed to diminish her spirit.  The result is a one-woman jihad against self-defeating weakness and letting the bastards get her down.

While her songs are unmistakably feminine in their viewpoint, any overlap with feminism in its formal or political sense is probably incidental; the emphasis on freedom here is personal and / or tribal.  Free your mind and your ass will follow.  Taken as a whole, Lizzo’s songs include a narrative in which ideas about physical beauty and desirability aren’t so much rejected as they’re reevaluated and reassigned (and occasionally weaponized).  Her lyrics abound with references to hair and nails, salons and shampoos, fresh photos with bomb lighting.

‘Truth Hurts’, like all Lizzo’s work, draws upon an inexhaustible well of confidence…though it’s interesting that as listeners, we’re not privy to the process of gaining that confidence.  Instead, we’re presented with a finished product; it’s an answer, not a question.

Michael Strum: “‘I think Lizzo is good for America, and for rap, and for music, and for women (particularly girls) and — let’s be real — for humanity. She’s unapologetically her, and strong, and I love that, particularly as a father to a girl. She says things like ‘This is me, and it’s not going to change,’ and ‘I’ve never been ‘sample size.’ I’ll never be ‘sample size’ … And I ain’t ‘plus sized’ I’m MY SIZE’ and ‘Boss up and change your life.’ That’s the best word for Lizzo: ‘Boss.’ And we see that on ‘Truth Hurts’: good wordplay and Lizzo showcasing her wide-ranging vocal talent. Boss. The mix is fun, and representative of her diverse skillset and background, rapper to singer to flutist. Boss. Detroit to Minnesota by way of Houston. Boss. ‘Truth Hurts’ gives us Lizzo the musician, rapper, artist, role model, and Boss.”

Rolling Stone: “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.

Rolling Stone Greatest Songs

Rolling Stone 500 Greatest Songs: Townes Van Zandt, ‘Pancho and Lefty’ (#498)

Written by a romantic poet disguised as a quasi-homeless troubador, Townes Van Zandt’s ‘Pancho and Lefty’ is, in Van Zandt’s own words, “about two Mexican bandits I saw on the TV.”  And that’s at least partly true; the song is about two Mexican bandits, and it’s possible that Van Zandt saw them or someone like them on TV (though I’d be reluctant to stake my life or reputation on that being a fact)…

…but Van Zandt being the poet that he was, that’s not all ‘Pancho and Lefty’ is about.

It’s also about the gulf that exists between the tawdry demands of real life and the bright glories of mythology.  It’s about friendship and betrayal, loneliness and the slow cruel decline of old age.  Pancho may have met an early death, with no one around to hear his dying words, but he gets all the good press, and was at least spared the indignity of dying cold and alone and obscure in Cleveland.

Now, I strongly suspect that Townes Van Zandt, who passed away in 1997, would not have described or explained anything about his most famous song in the same way I just have.  I don’t know for certain, but my guess is that he’d say he simply wrote it down as it occurred to him, and that the song speaks for itself, independent of whatever his intentions were (assuming he had intentions).  Whatever you get out of it, I think he’d say, then that’s what’s there.

The stories tell how Pancho fell
And Lefty’s living in a cheap hotel
The desert’s quiet and Cleveland’s cold
And so the story ends we’re told
Pancho needs your prayers, it’s true
But save a few for Lefty too
He only did what he had to do
And now he’s growing old

I wouldn’t say that the overall tone of Van Zandt’s body of work is one of despair — there’s joy to be found too, but it’s always tempered by the certain knowledge of human failure and the looming specter of mortality. 

Hey, it might not get better, but at least one day it’ll all be over.

Michael Strum: “First off, what a rock and roll name! ‘The Late Great Townes Van Zandt’ is a wonderful album with a great title. We’ll circle back to its release year — 1972 — as we move down the list. ‘Pancho and Lefty’ is incredible fun lyrically, and quite surprising: ‘fast as polished steel’ doesn’t take you where you think you’re going, nor does its rhyming couplet ‘for all the honest world to feel’, but you walk away happy. Fun rhyme structure. ‘Pancho and Lefty’ is relaxed storytelling, comfortable with itself, with great instrumentation. Horns are a nice touch, and not overdone. This song has it all: lyrics, melody, instrumentation, production. Risking blasphemy, I’d say that the songwriting quality here recalls B. Dylan. Far too low at 498.”

Rolling Stone: 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.”