1. Kinky Friedman, “The Ballad Of Charles Whitman” (1973)
Southern-fried satirist Kinky Friedman has made a career out of bad taste and button-pushing. He is, after all, the smartass provocateur who titled a sensitive exploration of the Holocaust and the Jewish diaspora “Ride ’Em Jewboy.” So it isn’t surprising that his song about mass-murderer Charles Whitman is gloriously irreverent and wildly offensive. Shooting from a clock tower at Friedman’s alma matter, the University Of Texas At Austin, Whitman killed 14 people and injured dozens more before he was shot to death; an autopsy revealed that he had a brain tumor which might have altered his mental state. Friedman brings all this into his high-spirited, upbeat, tongue-in-cheek hootenanny about Whitman, which describes his final spree and death as “a lovely way to go,” and includes perky couplets like “He was sitting up there with his .36 Magnum / laughing wildly as he bagged ’em.” In the song’s final line, Friedman cheekily warns, “There’s still a lot of Eagle Scouts around.”
2. Robbie Fulks, “She Took A Lot of Pills (And Died)” (1996)
Most country songs wait until the last verse to lower the hammer on their unlucky protagonists, but the burgeoning starlet in Robbie Fulks’ acidic ditty goes from toast of the town to cooling corpse in only four lines. Fulks’ honky-tonk tune is incredibly catchy, even when he’s describing the scuttle of the rats in her walls. The song merely reflects, without sentiment, the cruelty of a world that turns 20-year-old ingénues into 40-year-old has-beens, and digs them up only when they’re worth singing about.
3. Jim Carroll Band, “People Who Died” (1980)
Sometimes inspiration comes from a totally obvious place. In the case of Basketball Diaries author Carroll, it couldn’t have been any plainer: He knew a lot of people who died before their time. So he wrote a tribute to them—a funny, speedy song that sounds almost careless in the way he tips his hat to everyone from 12-year-old glue-sniffer Teddy to “Sly in Vietnam [who] took a bullet in the head” to the one he misses most of all, Eddie, who “got slit in the jugular vein.” But Carroll’s band rocks so insistently that it’s impossible not to sing along—and feel great doing it.
4. The Beatles, “Maxwell’s Silver Hammer” (1969)
George Harrison and John Lennon both complained about how long it took to record Paul McCartney’s cheerful ode to a serial killer, the former subtly (“[It’s] just something of Paul’s. We spent a hell of a lot of time recording this one,” Harrison told Rolling Stone in 1969) and the latter in his 1980 Playboy interview. It certainly does sparkle with the same bright-and-smiling professionalism with which the title character goes about his job; in a way, it’s a precursor to Dexter and American Psycho. Its rousing tune and crisp guitar leads make it sound almost of a piece with “Yellow Submarine” or “Octopus’s Garden,” until the lyrics start to cohere.
5. Vampire Weekend, “Jonathan Low” (2010)
The only surprising thing about Vampire Weekend’s contribution to the Twilight soundtracks is that it took them three movies to get around to it; between their name and the franchise’s love of crossover indie, it’s a natural fit. The only real jolt is how literally the band takes the paycheck and runs with it: “Jonathan Low” is about killing the titular Jonathan Low, and the lyrics are just ambiguous enough that it could seriously be about killing a vampire. (In the movie, sadly, it’s just used to soundtrack Bella and Jacob riding a bike.) The feeling is the usual sunny, wide-open jangle—there’s a little early-’80s XTC in there—but the chill is underlying: “Blood of his friends was gone beneath snow.” Vampire Weekend’s members don’t get to write songs like that for their day jobs.
6. Prince, “1999” (1982)
“Everybody’s got a bomb, we can all die any day—oww! / But before I let that happen, I’ll dance my life away.” The title hit from Prince’s fifth album offers one of his most memorable (and questionable) life lessons: When the apocalypse comes, the only sane way to handle it is to chuck everything and, as the coda insists, parrrty! End-of-the-Cold-War politics made it into a fair amount of Prince’s songs during this period: “Ronnie Talk To Russia,” from a year before “1999,” was more frantic, while “Free,” also on the 1999 album, was an unabashedly pro-American-freedom rock ballad, whose message showed up again on “America” on Around The World In A Day in 1985. But compared to those songs, “1999” is as seductive as “Do Me, Baby”: Prince’s version of partying down to the end of the world sounds totally irresistible, thanks to that instant-classic synth riff and some tricky vocal layering, courtesy of guitarist Dez Dickerson and keyboardist Lisa Coleman offering support singing the lyric.
7. The Only Ones, “Why Don’t You Kill Yourself?” (1980)
Like many of The Only Ones’ songs, “Why Don’t You Kill Yourself?” is seemingly about one thing (telling a friend who’s gone too far one too many times that his credit’s run out), but it’s mostly about heroin. Songwriter Peter Perrett had a drug habit that horrified Johnny Thunders himself; when Perrett sings to a friend who had his stomach “pumped four times already this week,” he’s essentially singing to himself. “Why don’t you kill yourself?” bounces the chorus. “You ain’t no use to no one else.” But the anthemic guitar solos are almost as good as on “Another Girl, Another Planet.” The rest of the song is just as eloquently grim (“You called out from a gutter / I couldn’t hear the words you muttered”), punctuated by a pop-punk chorus that’s almost ready for radio. Almost.
8. Nick Lowe, “Marie Provost” (1978)
Nick Lowe understands that good storytelling is all about the details, even if you have to fudge them a bit. Marie Prevost was a Canadian actress who enjoyed stardom in the 1920s and worked with everyone from Ernst Lubitsch to Lewis Milestone. She was also an alcoholic with emotional problems, difficulties that began to overwhelm her around the beginning of the sound era. She died alone at the age of 38, and the barking of her dog, who’d tried to bite her to wake her up, let her neighbors know that another star had fallen in Hollywood. But in Nick Lowe’s hands, Marie Provost (note the change in spelling) couldn’t cope with the talkies and ended up consumed by her “hungry little dachshund” because, hey, “even little doggies have got to eat.” Or, put more succinctly, in the song’s grimly catchy chorus, “she was a winner / who became a doggie’s dinner.”
9. Elliott Smith, “Son Of Sam” (2000)
The late Elliott Smith swore “Son Of Sam” wasn’t actually about David Berkowitz; “it’s just an impressionistic song about destruction and creativity, I guess,” he claimed. That could be true, but lines like “couple-killer each and every time” and “acting under orders from above” certainly don’t make that point too well, and the song sketches out the start of a killing spree with frightening concision: “told the boss off and made my move… lonely leered, options disappeared, but I know what to do.” Nonetheless, it’s the peppiest song on Figure 8 by a large margin—the piano solo is a killer—so DreamWorks went ahead and released it as the single.
10. Jellyfish, “The Ghost At Number One” (1993)
On its second and final album, Spilt Milk, power-pop revivalist Jellyfish must have known any commercial ambitions it had back in 1990 with its first album couldn’t survive the grunge era; few bands could’ve been so massively antithetical to what was in the air. Still, the group shot some videos, and “The Ghost At Number One” briefly got MTV airplay; it’s about as aggressive as Spilt Milk gets, so maybe someone thought they could fool people. “The Ghost At Number One” is possibly about Jeff Lynne—there’s no other obvious explanation for the line “Mrs. Lynn[e?], the fruit of your labor gives us a savior”—but it’s disturbingly applicable to Kurt Cobain, from the line about a man “shooting up his poison,” then sitting alone and writing songs. “How does it feel to be the only one who knows you’ve been buried alive?” they ask, and there’s no good answer for the future savior. “The king of rebels hit the jackpot,” but everything after that is downhill.
11. The Decemberists, “The Rake’s Song” (2009)
Easily the catchiest song from The Decemberists’ tricky 2009 rock opera The Hazards Of Love, “The Rake’s Song” offers the backstory of the album’s antagonist, a charmer who methodically murdered all of his children after his wife died in childbirth. It’s a fist-pumping number, even—or perhaps especially—when Decemberists frontman Colin Meloy recounts the details of each killing. Seems The Rake did in his kids Edward Gorey-style: feeding one foxglove, drowning another, and so on. As the music rises to a crescendo, Meloy sings, “Expect you think that I should be haunted / But it never really bothers me,” and the background singers shout, “All right!” And for that moment, it does sound all right.
12. Miles Kurosky, “An Apple for An Apple” (2010)
Beulah never shied away from setting grim sentiments to deceptively pretty music; on his solo debut, Miles Kurosky ups that logic to a new level with a five-minute epic reveling in the liberating possibilities of a plague. “Bring out your dead, kids,” he starts, and he’s off: “in this life, you’ll never be free.” Death, though, is freedom: he bites into the Adam’s apple (“I did my part and I took a bite”). “I fell hard for disease,” he confesses, “because it made me feel alive.” The music’s positively martial, all C-major triumph and peppy horns, which is the only way to ignore the fact that “they pickpocket your grave.” Even in the midst of death, people still act like jerks.
13. Tindersticks, “My Sister” (1995)
Feel-bad champ Tindersticks gave it a bit of a rest with “My Sister,” eight spoken-word minutes arranged to sound like breezy lounge fare. The story is as grim as can be: the narrator’s sister goes blind at 5, accidentally burns down the house when she’s 10 and kills her mom, recovers her sight at 13 (after falling down a well!), shacks up with an abusive gym teacher who hits her so hard the right side of her body gets paralyzed, and dies at 32. Meanwhile, the music is all jazzy sprawl (the trombone solos are hilarious if you’re in the right mood), a break from the Tindersticks’ usual alternation between coiled intensity and deep-dish melancholy.
14. Tom Lehrer, “The Irish Ballad” (1953)
Satirist Tom Lehrer was always about the cognitive dissonance between his jaunty piano tunes and his grim content, ranging from bleak looks at impending nuclear catastrophe in “Who’s Next” and “So Long, Mom” to more offhanded description of necrophilia (“I Hold Your Hand In Mine”) and, well, pigeon-murder (“Poisoning Pigeons In The Park”). But few of his songs are as relentlessly grim as “The Irish Ballad,” and none combine graphic gore and earworm-ready catchiness so effectively. He lays out his thesis in the first verse, promising a song about a maiden who “didn’t have her family long… not only did she do them wrong, she did every one of them in.” And then each subsequent verse describes a ghastly murder, as she drowns, burns, and poisons her parents and siblings, then finishes things off with a spot of cannibalism. Come to think of it, that is remarkably like the average Irish ballad, only with fewer verses and less of a dirge-like tone.
15. Elton John, “I Think I’m Going To Kill Myself” (1972)
A song so cheerful, its bridge features actual tap-dancing from “Legs” Larry Smith, Elton John’s “I Think I’m Going To Kill Myself” (as heard on 1972’s Honky Château) finds its teenaged protagonist contemplating suicide over bright, peppy piano chords, breaking out his titular threat in a vaudevillian refrain that practically begs for high-kicking chorus girls. Bernie Taupin’s opening verse is straight-up Charlie Manson, lamenting the way the human race has become a “waste of time,” with “people… swarming around like flies.” But as with so much adolescent misanthropy, it’s quickly revealed that his desire to end it all is mostly a selfish cry for attention to “get a little headline news,” and to pay his family back for perceived slights like not letting him use the car and enforcing an early curfew. “I’d like to see what the papers say / on the state of teenage blues,” John croons. They’d probably say teenagers are as mixed-up as ever, just like the contradictions here between grave pronouncements and upbeat melody.
16. Warren Zevon, “Excitable Boy” (1978)
Few musicians were as skilled at giving nasty songs an upbeat spin as Warren Zevon, who sang about killers, con men, and all-around bad dudes in a tone that said, “But really, they’re okay guys if you get to know them.” The title track to Zevon’s 1978 album Excitable Boy is a fine case in point: Zevon walks listeners through the day of an eccentric fellow who goes from acting out at dinner to building a cage out of the bones of one of his rape victims. All the while, the background singers coo and the saxophone wails, like the swingin’-est dance party any psychopath ever had.
17. The Eels, “Last Stop: This Town” (1998)
The Eels’ 1998 album Electro-Shock Blues is a beautifully realized concept album about the sister of lead singer E, and her suicide. The result is appropriately bittersweet and melancholy, but the first single, “Last Stop This Town,” manages to make mourning peppy and infectious, even as the opening lyrics, “You’re dead, but the world keeps spinning” betray the song’s grim subject matter. It’s heartbreak you can dance to, complete with scratching courtesy of producers The Dust Brothers, and a music-box melody that spins E’s poignant contemplation of his sister’s afterlife into pure sonic sugar.
18. Nena, “99 Red Balloons” (1983)
“This is it boys—this is war!” may well be the most archetypally ’80s pop lyric ever written, give or take Pet Shop Boys’ “S-H-O-P-P-I-N-G, we’re shopping.” The battlefield wasn’t the love of a contemporaneous Pat Benatar hit, but part of an actual ground war—or really, an air war; this is, after all, a song about balloons kicking off a nuclear blitz. The doot-doot-doot bassline, the speedy new-wave verses, and one of the all-time plastic synth riffs were irresistible even to Americans who knew no German when Germany’s young pop siren issued the original “99 Luftballoons,” and the English remake has a bit more vigor: Nena got to address the world, and rose to the occasion. That’s why a song about nuclear holocaust became one of the decade’s biggest party ravers.
19. Felt, “All The People I Like Are Those That Are Dead” (1986)
Like a grimmer Morrissey, the cultishly beloved Lawrence (he uses no last name, and it’s never been verified anyway) mopes his way through “All The People I Like Are Those That Are Dead.” The song finds the narrator despising his hometown: he’s been around, and “seen what God has done.” Whether he means all of his personal friends are dead (or whether he can’t relate to anyone besides dead authors and creators to begin with) is unclear, but the rage isn’t: At one point, he wonders “Maybe I should take a gun and put it to the head of everyone.” But the music jangles on: Most of the song is built around a breezy organ keyboard that won’t stop racing on and on. It’s not really that surprising that Belle & Sebastian’s Stuart Murdoch cites Felt as a primary inspiration: That mix of grimness and unexpected melodic feyness is key.
20. Terry Jacks, “Seasons In The Sun” (1974)
Loosely adapted from Jacques Brel’s “Le Moribond,” Terry Jacks’ bitter bubblegum hit is a dying man’s farewell to his family and friends. Skipping over Brel’s apostate goodbye to a well-meaning priest and a verse dedicated to his soon-to-be widow’s lover, Jacks substitutes mawkish doggerel sung in a clenched, wobbly voice and backs it with lagging acoustic guitar and cooing backing vocals. Where Brel seems sanguine about the prospect of death (“I die among flowers, peace in my soul”), Jacks is almost starry-eyed. Then again, considering that “Seasons” went on to sell 14 million copies worldwide, death was the best thing that ever happened to him.
21. Richard Thompson, “Now That I Am Dead” (1990)
First released on French Frith Kaiser Thompson’s 1990 album Invisible Means, this tongue-in-cheek take on death as a career move has found a home as a staple of Richard Thompson’s live sets. (His chipper rendition is actually preferable to John French’s “Monster Mash”-like vocals.) Sung from beyond the grave, the first-person account of a “composer decomposing” skewers the practice of waiting until artists have passed before giving them their due. “Too bad my genius was discovered after my coffin was covered,” he says, taking shots at lawyers, agents, and critics who turned a blind eye while he was still drawing breath. If only there were some way to get those frustrations out while the singer was still alive.
22. Pete Droge, “If You Don’t Love Me (I’ll Kill Myself)” (1994)
Nothing says “marry me” like a knife to your own throat. At least that’s the gambit behind Pete Droge’s modern-rock hit, which lays it out neatly in its opening couplet: “If you want, I’ll be by your side / If you don’t, maybe suicide.” Chances are, we’re not meant to take the threat any more seriously than his promise to “make you a star and… make you a queen,” but he takes that one back while leaving the prospect of self-annihilation standing. Perhaps the saddest irony is that Droge’s song was read by the masses as a promise of steadfast love, when it’s actually a cry for help.
23. Hank Williams, “I’ll Fly Away” (1951)
Gospel music is full of upbeat songs from true believers aching to shuffle off this mortal coil so they can be reunited with their Lord and savior in heaven. Sinner-turned-country-saint Hank Williams offers a memorable variation on this theme in his rendition of Albert E. Brumley’s enduring hymn “I’ll Fly Away,” as Williams rhapsodizes about that halcyon moment when his earthly travails will end and he’ll “fly away” to God’s celestial shore. It’s a song about transcending this corrupt secular world for heavenly rewards, made all the more poignant in that it came from an artist who was only a few years away from dying himself.