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.”

Rolling Stone Greatest Songs

Rolling Stone 500 Greatest Songs: The Supremes, ‘Baby Love’ (#499)

Signed to Berry Gordy’s Motown label in 1961, it took a few years for the Supremes — local Detroit girls Diana Ross, Mary Wilson, and Florence Ballard — to find their brand, their sound

…but when they found it, they really found it.

Between 1964 and early 1967, the Supremes produced a mind-boggling nine singles that went to #1 on the US pop charts, all written and produced by hit-makers Brian Holland, Lamont Dozier, and Eddie Holland.  ‘Baby Love’ is the second of these nine #1’s, following ‘Where Did Our Love Go?’ and followed by ‘Come See About Me’.[1]Though ‘Come See About Me’ was actually recorded before ‘Baby Love’.

All these songs are very much of a piece, chapters in the same dreamy American romance, sugary and shimmering with hope and sensitivity.  What sadness exists here is of the High School Confidential variety, temporary as a prom dress and worn for specific effect in a specific situation. 

The Supremes were literally teen-aged girls in high school when they were signed to Motown. At the time ‘Baby Love’ was recorded, the oldest of them, Florence Ballard, was 21; Diana Ross and Mary Wilson were just 20.  So…no longer girls, exactly, but not so far distant from girlhood either.  ‘Baby Love’ was written and arranged by men, performed by women, but the proximity to the fictional tropes of girlhood and its mythical purity — ‘Baby Love’ is about as wholesome as it gets — is downright palpable, which may help explain the song’s enduring life.  It’s my understanding that actual girlhood is a savage fucking jungle of heartbreak, fear, and treachery. To be fair, a lot of actual boyhood is like that too.  Or at least it was in my experience.

I searched in vain for a list of who played what on ‘Baby Love’, in the hopes of confirming what my ears were telling me (is that a goddamn vibraphone?).  All I know is that members of the Funk Brothers, Motown’s legendary backing band, played on the song, and that it was produced by Holland, Dozier, and Holland.  Still, it has all the hallmarks of the Motown sound.  I’ve yet to categorize exactly what those hallmarks are, but no one’s going to mistake a Motown song for anything else, that’s for certain.

Michael Strum: “Is there anything more American than the Supremes? Listening to them makes me profoundly happy. I feel the same way watching Michael Jordan highlights or reading about the Apollo program. It’s exhilarating to see people do something as well as it can be done. That’s what we get here: this is as well as pop music can be done. The production, the musicianship, the execution; it’s all simply first-class. I think the talent and skill presnt is unassailable, even if this isn’t your cup of tea. Excellent selection.”

Rolling Stone: Diana Ross wasn’t the strongest vocalist in the Supremes, but as the Motown production team discovered, when she sang in a lower register, her voice worked its sultry magic. Berry Gordy instructed the Holland-Dozier-Holland songwriting team to come up with something that replicated “Where Did Our Love Go,” the Supremes’ first Number One single. He thought the result wasn’t catchy enough and sent the group back into the studio. The result: the smoky “Oooooh” at the start. “Baby Love” went to Number One too, the first time a Motown group had topped the charts twice.


1 Though ‘Come See About Me’ was actually recorded before ‘Baby Love’.
Rolling Stone Greatest Songs

Rolling Stone 500 Greatest Songs: Kanye West, ‘Stronger’ (#500)

Aaaaaaaand right off the bat, we’ve got Exhibit A on why this blog is called the Opposite of Cool, and why I was so relucant to write on music in the first place.  If I were a judge, and this a legal case, I’d be obliged to recuse myself.

Because this song…I don’t get it. 

And not getting it — not getting Kanye West, for fuck’s sake, who’s practically the poster child for modern pop celebrity — makes me question my qualifications for writing on pretty much anything recorded in this century. 

It’s not that I dislike ‘Stronger’ so much as I just don’t get it.  It doesn’t register with me.  I don’t feel awe, nostalgia, revulsion, anger, or admiration listening to it; just a vague dissociative bemusement.  It’s a story from an unfamiliar tradition told in a language I don’t understand.  I don’t have an in with this material.  I don’t know what I’d connect it to, if indeed it connects to anything other than Kanye West’s obsession with Kanye West.

What I’m running into here, I think, is the ubiquitous narrative of celebrity.  Most notable musicians have a celebrity narrative — a weird mix of legend, gossip, history, and trivia — that’s woven in and through their actual art, and it’s very difficult, if not impossible, to separate story from output.  I’ve never had anyone speak to me about Jay Z’s music without telling me Jay Z’s origin story — you get the sense that what Jay Z actually recorded is almost beside the point — the same way almost no one will (or can) tell you about Hank Williams’ songs without including details about his unhealthy habits and untimely death.

Where Kanye West comes into this is that I’m realizing, listening to ‘Stronger’, that I have neither investment in, nor familiarity with, this particular celebrity narrative.  (Right or wrong, for better or for worse, when I think of Kanye West, I think Kim Kardashian and MAGA hats and George Bush not caring about black people.)  And that’s an issue here, because looking at the lyrics of the song and watching the video, my sense of it is that ‘Stronger’ is specifically about Kanye’s celebrity narrative; what was then (2007) the latest chapter in the Ongoing Saga of Kanye West, Celebrity.

I guess you had to be there.

Michael Strum: “There are things about Mr. West that I really like: his Chicago pride, his ear for production. He might have the best ear for a hook that I’ve encountered in this century. His Daft Punk renaissance here is skillfully envisioned and executed. Lyrically, there’s some fun and creativity, and also a couple of things that veer into ‘offensive at best’ territory. There’s good and also some bad, which seems, fitting, but it’s entertaining, and more interesting for the imperfections and opportunities. In that way, a highly appropriate opening number!”

Rolling Stone: 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.”

Rolling Stone Greatest Songs

Rolling Stone 500 Greatest Songs: Intro

I get questions.

Not that Opposite of Cool is exactly inundated with them, you understand, but questions do get asked on occasion.  (Amusingly, they’re almost never about anything OoC has actually discussed.)

The most common question I get is, How much is your comic book collection worth?  (Answer:  I’ve no idea.  No clue whatsoever.  Probably not much?  If you’re looking for value, you should go into real estate, diamonds, gold, arms smuggling, or heroin.  Those things have real dollar value.  Comics are just a mess of cheap paper held together with staples.  There’s no money in comic books.)

The next most common question is something along the lines of, How much are these Batman / X-Men / Spider-Man comics I’ve got from the early 90’s worth?  (Answer:  Unless they’re signed or have golden tickets to Willie Wonka’s chocolate factory stashed in their pages, probably less than what you actually paid for them in 1991 or whenever.  Comics follow the same laws of supply and demand as everything else, and everyone in the English-speaking world who ever thought of turning a profit through comic books acquired the same Batman / X-Men / Spider-Man comics that you did.  Supply exceeds demand, which means they’re not worth squat.)

And after that, the question I get most often is:

When will Opposite of Cool tackle music?  

I’d always intended that the answer to that question would be never.  I had (and still have, even if set on I’m ignoring them) a couple good reasons for this:

  1. I have no real expertise concerning music beyond my own unreasonably strident and snooty opinions.  Said opinions are largely the result of a decade spent working at Tower Records alongside my unreasonably strident and snooty (and much beloved) co-workers, who I’m afraid bear some measure of both blame and credit for whatever sonic aesthetic I’ve managed to cultivate (or failed to cultivate).  I’ve no hidden reservoir of musical knowledge, gossip, or insight from which to draw, which I fear will render much of what follows little more than a superfluous exercise in style and creative profanity.
  2. There’s also the matter of age and temperament.  To wit:  I remain all but certain that popular music as an art form peaked in 1973 and has been heading steadily downhill ever since, like unto a fiery meteor.  More, I’ve entered a phase in life where I recognize maybe one in five musical guests on Saturday Night Live.  I’m saying, I don’t exactly have my finger on the pulse of this particular artery of pop culture.  (And while we’re on this subject, I want you and your hooligan friends to take your arrthymic hip hop and your White Claw drinks and get the fuck up off my lawn.)

Still…at the behest of friend, contributor, and gentleman Michael Strum, I’ve (unwisely) acquiesced to writing about the Rolling Stone 500 Greatest Songs of All Time.  It’s likely there will be other contributors as well, particularly for songs or performers (or, hell, entire genres) where I might be especially out of my depth.  We’ll see.  I haven’t looked ahead more than seven songs or so, so I’ve no idea what to expect.

I hope you’ll join me and Michael (and other poor, doomed fools to be named later) on our long day’s journey into night.  See you there.