Also trips the line into Comedic Sociopathy, between the singer's reaction ("My best friend's on a shooting spree/Stop it, Debbie, you're embarrassing me!") and her frequent trivialization of the carnage before her.
Andrew Jackson Jihad employ this trope frequently. Their songs deal with issues such as self-loathing, social anxiety, poverty, homelessness, Parental Abandonment, racism, sexism, and lead singer Sean Bonnette's grandfather's terminal cancer, but manage to be extremely funny (and quotable) in the process. It helps that they have titles like "The Michael Jordan of Drunk Driving."
Bo Burnham employs this now and again in his songs—some of his most popular songs are about the KKK and pedophilia.
"Benny the Bouncer" by Emerson, Lake & Palmer, which is about a bouncer named Benny who is cut into pieces and brutally killed by Savage Sid. In contrast, the piece is sung by Lake in a ridiculous, heavy accent, while accompanied by Emerson on a honky-tonk piano, giving an impression of being upbeat and silly. Often considered as a filler track.
Tom Lehrer. More than half of his songs fits. "Irish Ballad" and "We Will All Go Together When We Go" are particular standouts. "I Got It From Agnes" is an unintentional example, since started out as one of his more lighthearted songs (similar to "The Elements" and such) on an enigmatic subject, since, as Lehrer has stated, it was written long before anyone had heard of AIDS. STDs were thought about far less commonly at the time, although the dark interpretation—inescapable today—just happens to conveniently fit among Lehrer's usual themes, so nowadays he's just gone with that interpretation.
"I Hold Your Hand in Mine" might sound innocent but hearing it makes you realise it's a representative of this trope. The same is true "My Home Town". And "The Old Dope Peddler."
And "I Got It From Agnes" is pretty damn dark even without taking AIDS into account; one character gets an STD from her father, "who gives her everything," and another gives it to his dog.
Mainly the songs where his "Slim Shady" alter-ego takes over.
The Dixie Chicks' "Goodbye Earl" is a jaunty number about a woman who enlists a friend's help to kill and dispose of an abusive husband. And it's played entirely for laughs.
"Pray for You" by Jaron and the Long Road to Love. Told by a preacher that he should pray for even those whom he hates, the narrator asks the following on his ex-wife: "I pray your brakes go out running down a hill / I pray a flowerpot falls from a windowsill / And knocks you in the head like I'd like to..."
Brian Eno's song "Baby's On Fire" is a cheerful uptempo rocker about... well, take a guess.
Ween's "Spinal Meningitis" complete with a squeakily sung impression of a terminally ill child would seem to be in the worst possible taste, although the chorus, sung in an adult voice: "Shine on mighty Jesus, spinal meningitis got me down" indicates a touch of religious satire. Maybe...
More prominent in the Ween side project, Moistboyz, in which singer Guy Heller, in character as Dickie Moist sings about over-the-top acts of violence, advocates harmful activities such as drinking and driving, and so on. For example, "Supersoaker MD50," in which a group of suburban teens in a truck do a prank drive-by in which they spray Dickie with a water gun. Rather than moving on since it's just a few kids having harmless fun, he decides to enact his revenge on them. And what kind of punishment does spraying someone with a water gun call for? He smashes their windshield with them still inside, which both sends glass flying in their faces and causes them to wreck and presumably die.
Schaffer the Dark Lord's "Clone-(expletive deleted)," tells of a post-apocalyptic future where robots are at war with mankind, and humans send clones of themselves as soldiers to fight in their place. One cloner decides to take advantage of the situation... It would be an understatement to say that it doesn't end well.
Stephen Lynch's "Baby", which is about realising how ugly his newborn daughter is. Contains the line "I always wanted kids / Is it wrong to hope for SIDS?"
The best example might be "For The Ladies", where he contemplates the best way to cause a miscarriage in his pregnant wife.
There's also his "Halloween", which involves the culinary possibilities offered by trick-or-treaters. Lyrics here.
Devo songs often contain underlying dark humour, but a select few sound almost like they're not joking.
Particularly songs from their early demo period: "I Need A Chick", "Baby Talkin' Bitches", "Bamboo Bimbo", "I've Been Refused", and "The Rope Song" may offend some.
"Mongoloid" and "Jocko Homo" might seem controversial for their titles alone, although they aren't particularly offensive songs themselves. The lyrics from the former portrays the titular "mongoloid" as a well-adjusted and productive member of society ("And he wore a hat/And he had a job/And he brought home the bacon/So that no one knew") and this actually resulted in Devo getting several supportive letters from parents to children with Downs syndrome. The latter has nothing to do with homosexuality, but is based on a religious anti-evolution pamphlet titled: "Jocko Homo, Heaven Bound King of the Apes."
"Triumph Of The Will": "It is the thing females ask for/When they convey the opposite" (The whole song can be interpreted as being about a rapist or a player who likes to think that he knows girls want him but are afraid to show their sexual side).
"I Desire" contains love lyrics written by would-be-assassin John Hinckley Jr. The joke may have been on Warner (Bros.) Records, who had to pay royalties to an inmate.
Sometimes Devo were controversial for their music videos - i.e., a talk show host refused to feature them after seeing the video for "Whip It" which she thought was offensive to women. In one case, the Jimi Hendrix estate forbade them from including their video for "Are You Experienced" on a DVD because there's a shot of a Jimi Hendrix look-a-like coming out of a coffin to play guitar, which they assumed was making fun of him.
Gerry Casale's alter ego, Jihad Jerry. Also, in a very early Devo performance, Jerry donned those "Chinese" toy glasses as a character called Chinaman (you can see a brief shot of him in their "Secret Agent Man" video).
Australian band The Self-Righteous Brothers have a whole string of songs which fit this trope, often sung in a pleasantly melodious fashion. A couple of examples — from "Now You're Gone":
Now your family want to take me to court
Just for having sex with your rotting corpse.
I love you so much more
Now that you're gone.
They are also responsible for such gems as "Daddy Drinks Because You Cry" and "(Too Much) Sperm In Your Eyes".
The Frogs' infamous "It's Only Right And Natural", where every song is written from the point of view of over-the-top sex-obsessed gay men - possibly the song that really Crosses the Line Twice is "Baby Greaser George", in which the narrator puts his "thing" in the mouth of a 3-month old in a stroller while dressed as a leather man, and gets a testicle bitten off. Dark comedy isn't all they do, but it's what they're most well-known for due to song titles like "Grandma Sitting In The Corner With A Penis In Her Hand Going 'No No No'".
The song "Maxwell's Silver Hammer" achieves this effect largely through Lyrical Dissonance.
And then there's the Bloodhound Gang's song "Lift Your Head Up High (and Blow Your Brains Out)".
And the classic "A Lap Dance Is So Much Better When The Stripper Is Crying."
Amanda Palmer has a thing for upbeat catchy songs with really dark lyrics, "Oasis" is a song about getting raped and then an abortion, but it's OK, because Oasis wrote her a letter. "Mandy Goes to Medschool" is a very groovy sort of cabaret song about back-alley abortions, and "Lonesome Organist Rapes Page-Turner", which is a fantastic and really rather amusing song that is about Exactly What It Says on the Tin.
A drinking song popular in some Australian universities at the moment. It starts at "My name is Jack/And I'm a necrophiliac/I get so hard/When I see a graveyard" and gets significantly worse from there. (No, You Do NOT Want To Know. Seriously.)
Like the rest of their music library, the song "I Lit Your Baby on Fire" by the politically incorrect grindcore band Anal Cunt is a thrashing, incomprehensible ode to doing Exactly What It Says on the Tin, complete with wonderfully heartwarming lyrics such as, "It screamed a little louder/And then it shut up."
This most certainly applies to the Doug Anthony All Stars, an Australian musical comedy trio whose repertoire included songs about necrophilia ("Necro-romancer"), bestiality ("I Fuck Dogs"), their desire to murder Oprah Winfrey ("Oprah"), the Twelve Apostles' drug habit ("Catholic Girls on LSD"), their wish to crawl back inside their mothers' wombs ("Mummy Dearest"), and snogging grandma ("World's Best Kisser"). And that's just for starters.
Noah And The Whale's "Jocasta". Unsurprising to anyone who knows the story of Jocasta, it involves actual baby death.
When the baby's born Oh, let's turn it to the snow So that ice will surely form Over weak and brittle bones Oh, let's leave it to the wolves So their teeth turn it to food Oh, its flesh keeps them alive Oh, its death helps life survive Oh, the world can be kind in its own way.
Big Black addresses issues such as murder, rape, necrophilia, suicide, racism, and the works. "Jordan, Minnesota" is a song about a parent-child molestation ring in the town that the song is named for. Their first LP, Atomizer, includes songs about the aforementioned molestation ring, a black man who's light-skinned enough to pass off as a white guy, a corrupt police officer, a guy bored with arson and easy sex (the only two things teens in rural America do for fun) and decides to combine them, a man who goes to "houses of ill repute," a wife-beater and/or fist-fucker, a recovering alcoholic who relapses, a veteran with shellshock who becomes a hitman, and two teens who go to a slaughterhouse for entertainment.
Their 2nd LP, Songs About Fucking, features asshole truck drivers, a Kraftwerk cover, a guy who has sex with other people's girlfriends, a young girl who slept away 15 years of her life and wanted to kill herself but couldn't, sexual humiliation as a habit, a killing method in which the throat is cut open and the tongue is pulled out through the hole, an eccentric man who parties all night, a fungus that can grow on bread and cause serious hallucinations if ingested, a mafia killing in which a parked car was rigged to explode when the target's car passed by, a guy who had sex with a woman, who refused his brother's earlier advances, and killed her with his shoe then hid her body in a pond while hosing down his truck with loud music on, people who slowly turn into what they hate most without trying, and a Cheap Trick Cover
They also had an EP whose cover art depicted a real life suicide victim whose head was split in two after shooting himself with a shotgun. The name of this EP? Headache.
The lyrics for Welsh Death metal band Desecration's song "I.A.I" are so vile it had to be abbreviated. On release of the album 'Gore and perversion' the band members were actually arrested and the original albums were destroyed due to the offensive nature of the songs which lies somewhere between this and terror. The original album artwork will either disgust you beyond belief or make you laugh. Find it all here if you dare. Extremely NSFW!
Jon Lajoie does this often in a lot of his videos. Probably the most obvious one is MC Extremely Inappropriate Rhymes in "WTF Collective 2":
I shake things up like [Michael] J. Fox when I get on the mic
And I drop my enemies like Christopher Reeves' horse
Post-Rock group Godspeed You! Black Emperor have a short, jaunty little acoustic guitar interlude entitled "Moya Sings Baby-O" at the beginning of "Antennas to Heaven," which is otherwise a dark, minimalist instrumental. The lyrics talk about abusing, ignoring, gouging the eyes of and feeding alcohol to a baby. It's entirely unexpected.
This interlude is a version of the Appalachian folk song "What'll We Do With The Baby-O" - given the Lyrical Dissonance, the song was probably intended as black comedy to begin with.
"Mr. Frump in the Iron Lung" is an upbeat song about the narrator visiting a man in an iron lung and having one-sided conversations with him until he dies.
"I Remember Larry" recounts how the singer was bullied (sometimes quite viciously and dangerously) and how he killed the bully.
"You Don't Love Me Anymore" is a ballad about all the ways the singer's girlfriend has tried to kill him.
"Christmas at Ground Zero" is about nuclear war.
"The Night Santa Went Crazy" details Santa Claus going on a killing spree at the North Pole.
"Trigger Happy" is sung from the perspective of a gun-crazed psycho who apparently believes that shooting people is the best way to solve problems and mentions that he accidentally shot his father and his cat on two separate occasions.
Met a little lady so pretty and young. She was quite the talker till the cat got her tongue. She oozed up beside me, I turned on my charm. Pretty soon she was completely disarmed. I said, "Girl, don't you fall to pieces on me", but she cried her eyes out. Literally. At the party at the leper colony.
"Good Old Days" consists of a lighthearted-sounding song where the singer warmly reminisces on his past, mentioning normal things to feel nostalgic about before revealing red flags that he is some kind of sadistic psychopath. In the first verse, he talks of how his dad would water the lawn or go fishing, his mother would bake biscuits or apple pie in the kitchen, and he'd spend his days torturing rats and flies in the basement. The second verse has him speaking fondly of a kindly neighbor named Mr. Fender before giddily recalling burning down his house and killing him. The third and final verse recounts how he shaved his high school crush's head and left her to die in the desert after taking her to the homecoming dance.
A good chunk of Velvet Underground's second album, White Light/White Heat. "The Gift", "Lady Godiva's Operation" and "Sister Ray" all have characters indulging in activities that end in somebody getting killed, all while the stories are narrated in a deadpan, if not outright playful, tone.
Virginia O'Brien's "Say We'll Be Sweethearts Again", a song about domestic abuse, is as hilarious as it is brutal.
A lot of Randy Newman's early songs were black-humored. For example, "Sail Away" is a Copland-esque ballad describing America as the promised land that is being used by a slave-trader to entice an African boy onto a ship and into bondage.
Warren Zevon reveled in this. There's "Excitable Boy" (about an insane young man who bites people, then rapes and murders his prom date, then "dug up her grave and built a cage with her bones"), "Roland the Headless Thompson Gunner" (about a Norwegian mercenary in Africa who's assassinated by the CIA, rises from the grave, and takes revenge), "Poor Poor Pitiful Me" (which begins "I lay my head on the railroad tracks and wait for the Double E; the railroad don't run no more, poor poor pitiful me"), and of course "Werewolves of London."
I used to love her, but I had to kill her. I had to put her, six feet under, and I can still hear her complain.
The end of the video for I Could Be the One, by Avicii and Nicky Romero.
The song "Another Irish Drinking Song" by Da Vinci's Notebook is this. It's basically explaining the singer drinks constantly because everyone's died. It starts with dad, mom, two brothers, a sister, and goes into uncles, grand-uncles, grandparents, a guy who went to Notre Dame, a Scotsman, a pedophile priest, and finally talking about when the singer dies, they want the Lord to kill the cast of Riverdance. And Michael Flatley too. The chorus is basically repeating "drink", then dance, sing, fight, throw up, pass out, and wake up to drink again.
Harry Chapin's "30,000 Pounds of Bananas" is about a truck driver who loses control of his truck going down a hill and dies in the ensuing crash (Based on a True Story, even). The whole thing's Played for Laughs, between the repeated mention of the bananas (the truck's cargo, and they end up splatted all over the road in the crash) and morbid humor (when the brakes fail: "He said 'Christ!' / It was funny how he had named the only man who could save him now..."). The song also spawned the "Harry, it sucks" meme from the band's reaction to Chapin's first couple attempts at writing an ending.
Celtic and Filk singer Marc Gunn wrote a lullaby for his daughter...about demons underneath her bed, that will eat her up if she doesn't go to sleep.
That is not a blanket...
"Prop Me Up Beside the Jukebox (If I Die)" by Joe Diffie. He asks that, should he die, his body should be stood up beside the jukebox with a "stiff drink" in his hand. The song starts off as a slow fiddle piece before abruptly shifting into upbeat honky-tonk.
Frank Zappa also falls into this trope. Two examples: Why Does It Hurt When I Pee? from Joe's Garage, probably the funniest song every written about getting a venereal disease, and Suicide Chump (from You Are What You Is), easily the funniest song about committing suicide.
Dead Kennedys: Many comedy songs about religion, war, murder, corruption. Music/Frankenchrist in particular is full of it!