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1. Johnny Cash, "A Boy Named Sue"
Johnny Cash's wise-country-storyteller persona lent itself naturally to story-songs, from traditionally inspired ballads like "Legend Of John Henry's Hammer" to funny goofs like "One Piece At A Time." But one of his best was the epic saga "A Boy Named Sue." Shel Silverstein's dense, witty lyrics follow the titular character on a hunt for the deadbeat dad who gave him his awful name and abandoned him in childhood. Turns out there was method to daddy's madness, which "Sue" accepts in the end, though not to such a degree that he's willing to repeat the process with his own theoretical future kids.
2. Kenny Rogers, "Coward Of The County"
In his heyday, Kenny Rogers also intermittently donned a wise-country-storyteller persona, though his story-songs tend to be less wryly funny than Cash's, and more tragic. For instance, "The Gambler," "Lucille," and the frankly horrifying "Coward Of The County," which was later made into a TV movie featuring Rogers in a key role. Like "Boy Named Sue," "Coward" follows a young man dealing with a bad paternal legacy—in this case, his father's prison-deathbed command to stay out of fights, 'cause "You don't have to fight to be a man." Eventually, the boy learns that poppa was wrong, and he proves to everyone in his judgmental little county that he ain't yellow after all. Too bad it takes the love of his life getting gang-raped to get him off his butt.
3. Jawbreaker, "Chesterfield King"
Viewed through the lens of all the lame emo that's followed it, Jawbreaker's "Chesterfield King" seems kind of quaint. But the song—a lone, bright gem amid all the sludge and glumness of the band's 1992 album Bivouac—is the prime example of Black Schwarzenbach's emerging literary bent, which the singer-guitarist would perfect on Jawbreaker's next two discs. With plainspoken yet vivid lucidity, Schwarzenbach opens the story in medias res, with himself and a female friend on the brink of romantic revelation. Fear chases him out of her house, after which he shares a smoke and a beer with a homeless woman outside a 7-11. Emboldened by the moment—and the bracing caress of autumn air, this being emo and all—he races back to his girl's house to seal the deal, poetically and inconclusively, of course. Lines like "I took my car and drove it down the hill by your house / I drove so fast" might sound a little too much like an, um, dashboard confessional, but "Chesterfield King" remains a perfect, roughhewn chunk of prose sunk into one of the catchiest punk tunes of all time.
4. The Temptations, "Papa Was A Rollin' Stone"
After the high-profile 1968 departure of Temptations singer David Ruffin, Motown songwriter-producer Norman Whitfield helped reinvent the group in his own image. With one foot planted in the classic Motown sound, and one stretching toward the new, hippie-friendly funk of Sly And The Family Stone, Whitfield worked with the Tempts to pioneer a trippy, socially conscious brand of psychedelic soul. It was a radical departure from the songs that had made the group famous, and it created its share of tensions. By 1972, the group had experienced even more turnover and was beginning to resent Whitfield's auteurist approach. But that tension isn't audible in "Papa Was A Rollin' Stone," an expansive track—the full version runs for 12 minutes—in which the singers take turns asking about the father they never knew, only to receive the same answer, "Papa was a rollin' stone." Even as grown-ups, they don't fully understand it. They know the details about a "jack of all trades" life of "storefront preaching" and other endeavors, but the sad truth is in the spacious instrumental passages, blanks that the absence that unites them has left them to fill.
5. Loudon Wainwright III, "The Man Who Couldn't Cry"
Loudon Wainwright III pulls off a tough trick with his country-music parody "The Man Who Couldn't Cry"—he pokes fun at tear-in-your-beer story ballads while also making his stoic protagonist genuinely sympathetic, resulting in a song that's both funny and surprisingly moving. (This is especially true of Johnny Cash's memorable cover on 1994's American Recordings.) The unnamed man loses the ability to cry after his tear ducts run dry during childhood. A series of bad things happen to him—his dog is run over, his wife leaves him, he loses his job, he's laughed at by a whore—but there's "still not a sniffle or a sob." (He's even sent off to jail—"you guessed it, no bail," Wainwright adds.) Finally, after he's sent to a mental hospital, he finally cries when it rains, and ends up crying for 40 days and 40 nights. On the 41st day, he dies from dehydration. But the story has a happy ending: the man goes to heaven and everything bad that happened to him in life is corrected. His ex-wife, for instance, dies of stretch marks.
6. Todd Snider, "Tillamook County Jail"
Singer-songwriter Todd Snider crafts a slyly humorous, Raymond Carver-esque snapshot of a slowly disintegrating loser in "Tillamook County Jail." The details given end up being as important as those only suggested: The first-person narrative begins with the protagonist wondering whether his woman will bail him out of jail, hinting that this isn't the first time he's been in trouble. There's a lump on his head and boot print on his chest from "the Tillamook County lie detector test," a "tough test not to fail." Finally, he tries to explain what got him here—it started with a fight with a guy on the highway, who said the protagonist "did some things that I didn't do." The cops chased him down the road and hauled him in. His story sounds fishy, but he remains unrepentant. If he ever gets out of jail, he's never coming back to Tillamook County. He'll just raise hell someplace else.
7. Drive-By Truckers, "The Deeper In"
"By the time you were born there were four other siblings," Patterson Hood explains at the start of the funereal-paced "The Deeper In." He goes on to tell the subject of the song her own story: how she met her wayward older brother for the first time when she was 19, how his motorcycle and "jawline" swept her off her feet and into a cross-country run from the law. Positioned as the first song on Drive-By Truckers' most satisfying and arguably most Southern album, Decoration Day, "The Deeper In" either shamelessly exploits the plight of two impoverished hicks, or movingly explains how one damn thing can lead to another. Their brother-sister common-law marriage might've lasted, if only the sister hadn't brought four more inbred kids into the world. But she did, which sets up Hood's devastating finale: "Last night you had a dream about a Lord so forgiving / He might show compassion for a heathen he damned / You awoke in a jail cell, alone and so lonely / Seven years in Michigan."
8. New Order, "Love Vigilantes"
Though not generally known for story-songs, New Order kicked off the classic 1985 dance-pop album Low Life with this fantastical tale of a soldier who gets his discharge orders and heads home, only to find his wife crumpled over in grief on their floor because—get this—he's actually dead! The lyric is as awkwardly phrased as a junior-high poetry assignment—"You just can't believe / The joy I did receive" is one particularly egregious line—but the ending remains a sucker-punch. Maybe the song's impact has something to with its ironically jaunty melodica solo and bouncy beat. Or maybe it's the simple yearning of the repeated chorus, "I want to see my family."
9. Bright Eyes, "Light Pollution"
Conor Oberst takes his time setting the scene for this simultaneously sad and triumphant character sketch, starting by remembering a friend who "loaned him books and mic stands" and taught him all about the human wreckage left behind by the free-market system. Then, out of nowhere, Oberst starts piling up the imagery from one particular night. There was a baseball game, and billboards shading the road, and a mall-front highway spitting neon. "And maybe he lost control fucking with the radio," Oberst wails, "But I bet the stars seemed so close at the end." The busy electronic track drops to a hush, and Oberst repeats "at the end" softly over a wisp of electric piano, remembering a man killed by the unchecked corporate sprawl he railed against in life.
10. The Kinks, "Come Dancing"
This late-period Kinks comeback hit doesn't rock as hard as the band's '60s and '70s classics, and at the time, it seemed like kind of a novelty number, with its retro music-hall melody and brassy arrangement. But "Come Dancing" is of a piece with Ray Davies' formidable body of songs about a vanishing England. Here, the song's narrator remembers "the local palais," where his sister went on chaste dates with boys, while the narrator and their mother stayed up waiting for her to come home. By the end of "Come Dancing," the dancehall has been replaced by a bowling alley and a car-park, and the narrator's sister has become an anxious mother herself. But he urges her to remember the innocent romance of the old days, and to dance again, if only to show a new generation how to do it proper. (Davies finds the past similarly bittersweet in the classic story-song "Do You Remember Walter?", in which he recalls an old classmate who he assumes is now "fat and married," and decides he's best left in the past. "People often change," goes the wise, crushing conclusion, "but memories of people can remain.")
11. Pulp, "David's Last Summer"
Another songwriter with a skeptical attitude about the future and a keen eye for detail, Pulp's Jarvis Cocker packs the seven minutes of "David's Last Summer" with details of a summer filled with cider, late-night parties, and a sharply remembered "small pale-skin bikini," the last before the responsibilities of adulthood kick in. By the time summer begins "packing its bags as it prepare[s] to leave town" it's clear that no other season will live so vividly in the imagination.
12. Joni Mitchell, "The Last Time I Saw Richard"
In her heyday, Mitchell preferred to offer impressionistic explorations of moments rather than full narratives, but because the moment she describes in "The Last Time I Saw Richard" has a history, she has to tell a little story in order to bring it to its conclusion. After an extended, somber piano intro, the narrator spends two verses remembering a collegial argument she had in a bar back in 1968—only three years before this song was recorded. Her friend Richard warned her not to be such a naïve romantic, falling over and over for "pretty lies," and she replied that studied cynicism can be a kind of romanticism too. Besides, every song Richard punched up on the jukebox that night was about "love so sweet." In the third verse, Mitchell sums up what happened next: Richard got married and "drinks at home now most nights with the TV on," while she still haunts the bars, though she'd rather be left alone. "Only a phase, these dark café days," she concludes. At the time, this song seemed to bring the curtain down on the '60s, but it still rings true to anyone who ever lived, loved, and fought with more passion than they do right now.
13. Jeannie C. Riley, "Harper Valley PTA"
This country-and-western standard is so much a start-to-finish narrative that it actually starts off "I want to tell you all a story…", and it inspired a film and a spin-off TV series. The saga begins when a child comes home with a note suggesting that the Parent Teachers' Association of her provincial school district finds her mother's short skirts and carousing ways inappropriate. The mother promptly shows up at the PTA's next meeting to call out every member by name and publicly reveal their cheatin', drinkin', sneakin'-around ways, winding up with the line "this is just a little Peyton Place, and you're all Harper Valley hypocrites." Riley then reveals, in the big finish, that this "really… happened just this way / The day my mama socked it to the Harper Valley PTA." Strangely enough, after the song became a hit, such country luminaries as Dolly Parton, Loretta Lynn, and Billie Jo Spears all recorded cover versions, indicating that the exact same thing "really" happened to their mamas, too.
14. Richard Thompson, "1952 Vincent Black Lightning"
Having covered English folk ballads like "Matty Groves" from his early days as guitarist for Fairport Convention, Richard Thompson is no stranger to the form. He updated the traditional highwayman ballad with this song from 1991's Rumor And Sigh, spinning the tale of a dashingly dangerous robber who bonds with a red-haired beauty over their shared love for the classic motorcycle of the title. It's become his most popular song, and it shows up in nearly every concert he plays, with good reason: It's a masterpiece, a great showcase for Thompson's amazingly fluid fretwork and a powerfully resonant, simple tale of doomed romance that doesn't have a single wasted word.
15. Bob Dylan, "Lily, Rosemary, And The Jack Of Hearts"
Dylan has so many story-songs under his belt, from the surrealist goof of "Bob Dylan's 115th Dream" to the ripped-from-the-headlines "Lonesome Death Of Hattie Carroll," that it's hard to single out just one. But one of his finest yarns turns up on 1975's Blood On The Tracks—this Western about a charming rogue who blows into town and gets the better of villainous mine owner Big Jim, with the help of Jim's showgirl mistress Lily and put-upon wife Rosemary. The song's cinematic sweep makes it feel like it might have been a great film in the hands of a director like Howard Hawks or Dylan's friend Sam Peckinpah. And in fact, Dylan tried at least once to get a screenplay based on "Lily" off the ground.
16. Simon & Garfunkel, "Save The Life Of My Child"
Paul Simon also has his share of ballads and story-songs, but few of them are as satisfying or as pointedly conclusive as 1968's "Save The Life Of My Child," which is as much metaphor as story: As a boy sits perched on the ledge of a tall building, a crowd forms, waiting for him to jump. As his mother panics, the bystanders and the cops take the opportunity to dismiss today's youth as disrespectful, irresponsible druggies. The mass conclusion: Kids today just aren't cut out to survive. Naturally, the boy surprises them all, scoring a point for '60s counterculture by exceeding their expectations and proving them all wrong.
17. The Handsome Family, "After We Shot The Grizzly"
As a lyricist, Rennie Sparks has a lot in common with writers like Flannery O'Connor and Patricia Highsmith, both for her narrative sensibility and her darkly comic, macabre attitude. "After We Shot The Grizzly," from last year's Last Days Of Wonder, follows the grim misadventures of a group of plane-crash survivors who struggle in vain against their inevitable descent into savagery and death—sort of Lost as portrayed by the Donner party. Brett Sparks' understated performance and Rennie's deadpan sense of humor make the song something of an anti-epic, with an increasing sense of twilit mystery as the survivors disappear one by one into the darkness and the silent waves, never to be seen again.
18. Elvis Presley, "In The Ghetto"
"In The Ghetto" might be a more soulful song if Elvis Presley didn't sound entirely aware of how very, very soulful he sounds, but the material is still mighty sad—and general enough to be an iconic illustration rather than the story of any one specific person. In an unspecified Chicago ghetto, "a poor little baby child is born" to a mother who can't deal with another mouth to feed. Growing up impoverished and hungry, he also grows up mad and desperate, leading to a tragedy that Mac Davis' lyrics present as inevitable. Davis' much-covered (even on American Idol) song could stand to be subtler—the bridge where Presley demands "People, don't you understand / The child needs a helping hand / Or he'll grow to be an angry young man some day"—is particularly overwrought. Then again, it's also true.
19. Harry Chapin, "Cat's In The Cradle"
Another weepy classic that's overwrought and true at the same time, Harry Chapin's "Cat's In The Cradle" is a morality tale for absentee parents who have priorities other than their kids. When the narrator's son is a child, he idolizes his dad, "But there were planes to catch and bills to pay… He learned to walk while I was away." Before long, that idolizing kid has become a busy teen, then a grown man who blows off dad the way dad used to blow him off back in the day. The irony, of course, is that the kid spent his childhood saying "I'm going to be just like dad when I grow up," and of course, he's right.
20. Arlo Guthrie, "Alice's Restaurant"
Not so much a story-song as a story sandwich breaded with slices of song, Arlo Guthrie's ironic anti-war saga is almost hypnotic in its meandering, shaggy-dog exigencies. Guthrie starts off "This song is called 'Alice's Restaurant,' and it's about Alice, and the restaurant, but Alice's Restaurant is not the name of the restaurant, that's just the name of the song, and that's why I called the song 'Alice's Restaurant.'" This kind of folky, circular, stoned-sounding double-talk explains why the song takes upward of 20 minutes to perform. Also, the song isn't really about Alice or the restaurant, it's about (to cut to the punchline) how Guthrie supposedly was rejected as a draftee because he was a litterbug. Love it or hate it, it pretty well sums up the '60s.
21. T-Bone Burnett, "The Strange Case Of Frank Cash And The Morning Paper"
Before he was the Grammy-winning music producer, arranger, and composer for films like Oh Brother, Where Art Thou? and Cold Mountain, T-Bone Burnett was a performer in his own right, churning out terrific quirky songs like "The Strange Case Of Frank Cash And The Morning Paper," in which a down-on-his-luck hustler living on "lonely street" discovers that his daily newspaper lists the scores for next week's football games. He makes so much money on sports betting that he moves out of his crummy apartment and into "a sprawling estate on the lake / And by that, I don't mean by the lake, I mean ON. THE. LAKE.") But lo and behold, when the football season starts up again, "the damned paper had ceased to prognosticate." Panicked, he rushes back to his old apartment and demands the paper from the new resident, leading to a situation so dire that Burnett himself has to step in to straighten things out. It's a tremendously funny song in spite of its straight-faced delivery, though the best moment comes when Frank Cash, aware that he's just a character in a song, proclaims—ineffectually, of course—that he doesn't believe in Burnett, and that "This song is over!"
22. Barry Manilow, "Copacabana"
Barry Manilow's irrepressibly catchy, annoyingly enduring Billboard Top 10 hit had a strong enough storyline that it eventually became a musical, though ask any 10 people on the street, and they'll probably be able to sing the first line (Her name was Lola, she was a showgirl") and the chorus, and not much else. Somewhere in between, Lola and her bartender boyfriend Tony work at the Copacabana nightclub until a rich rival for Lola's affections takes Tony down. Cut to 30 years later, when Lola sits alone in her old showgirl outfit "and drinks herself half-blind" at the Copa, now a disco that presumably plays songs like this one.
23. Neil Young, "Cortez The Killer"
The soaring mini-epic anchor to Neil Young's 1975 album Zuma opens with an extended Crazy Horse jam session before segueing into a delicate, occasionally cryptic mix of the historical and personal. In broad strokes, Young tells the story of conquistador Hernán Cortés, who conquered Mexico for Spain in the early 1500s. ("He came dancing across the water with his galleons and guns / looking for the New World in that palace in the sun.") At the same time, he gives reverential treatment to the Aztec figure Montezuma, "with his cocoa leaves and pearls," presiding over a world where "the women all were beautiful and the men stood straight and tall." There's no reference to the conflict itself; it's more a reverie for a lost world and a lost people, connected ever so delicately to a stanza about lost love. Then the song finally circles back to Cortés: "What a killer."
24. The Coup, "Nowalaters"
Over the course of The Coup's career, frontman Boots Riley has deftly explored literary genres ranging from feminist character studies ("Tiffany Hall") to atmospheric pulp fiction ("Me And Jesus The Pimp In A '79 Granada Last Night") to sophisticated social satire (the three-song story suite that opens Genocide And Juice). On "Nowalaters," Riley lends his gift for novelistic detail and messy humanism to a first-person coming-of-age story about a teen player whose backseat bumping and grinding leads to an unwanted premature pregnancy. The protagonist prepares himself for the solemn responsibility of fatherhood, but then discovers he isn't the baby's father after all. In most rap songs, this final twist would lead to a regressive moral about the innate duplicity of women, but Riley ends the song on a heartbreakingly gracious, tender note by sincerely telling the double-timing temptress, "Thank you for letting me go."
25. Eminem, "Stan"
Somewhere between funny and tragic, Eminem's saga "Stan" mostly comes in the form of an series of letters from a young super-fan who doesn't understand why his idol won't call him or answer his letters, even though "I left my cell, my pager, and my home phone at the bottom." Stan's clueless desperation veers between laughable and miserable; his life as he describes it is truly awful, and it's sad to think that he's pouring all his energy into reaching out to a celebrity who doesn't know he exists. Still, it's easy to laugh as he repeatedly goes over the top in his assumptions and demands. The chuckling ends when a despairing Stan crams his pregnant girlfriend into his trunk and deliberately drunk-drives off a bridge, too late for him to be reached by Eminem's warm, detailed, surprisingly caring response letter. It's almost as though Eminem is suggesting that celebrities occasionally don't know whether to be flattered or horrified by their most ardent fans.
26. Julie Brown, "The Homecoming Queen's Got A Gun"
Part parody of the endless '60s-era ballads about teen romances ending in tragic death ("Teen Angel," "Ebony Eyes," "Patches," etc.), part a standard entry in Julie Brown's Valley Girl character lexicon, and part just an enthusiastic novelty song, Brown's biggest radio hit told the story of a massacre at the big homecoming parade. Peppered with "like" and "totally," and sung in a cheerfully shallow bubblegum style that makes the song's horrible events amusing, the lyrics explain how Julie's best friend Debbie goes from bouquet-carrying, float-riding, pink-chiffon-wearing homecoming queen to cold-blooded mass murderer, "picking off cheerleaders one by one." Ignoring police warnings, Debbie keeps shooting until the cops gun her down: "She hit the ground and did a flip, it was real acrobatic / But I was crying so hard I couldn't work my Instamatic." The punchline? Just before dying, Debbie confesses that she "did it for Johnny," but, like, nobody actually knows who Johnny is. Bummer.