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.