Quiet-storm seduction sheathed in a dirty condom. Only the late Christopher Wallace and, ahem, R. Kelly could make such a hellaciously filthy and crass declaration of intent (“You must be used to me spending / And all that sweet wining and dining / Well, I’m fuckin’ you tonight”) sound so bubble-bath romantic. Pro Tip to the Fellas: If you slip this onto one of your sexy-time playlists, you’d better hope your lady friend has a well-developed sense of irony.

Truthfully, the twisted accusation “Are you thinking of me when you fuck her?” isn’t even the most memorable blue line from Morissette’s monster 1995 breakthrough single. That honor goes to one of the greatest sexual humble-brags ever spat at an ex: “Would she go down on you in a theater?” Alanis, to her credit, never revealed the identity of the ungrateful moviegoer, but when Dave Coulier, best known as Uncle Joey on the goopy TV sitcom Full House, told an interviewer the song was probably about him, all of North America groaned a collective “Ewww.”

The most irresistible F-bomb in Top 40 history. Although CeeLo’s profane middle finger to a gold-digging ex and her Ferrari-driving beau had to be smuggled onto the charts as “Forget You,” you just know the censors didn’t have their shriveled hearts in it this time. Thanks to the combination of the track’s finger-popping Motown bounce, Green’s churchy tenor and the unbridled exuberance of the chorus’s expletive—“I see you driving ’round town with the girl I love / And I’m like, ‘Fuck you!’”—this is like getting cursed at by one of those big yellow smiley faces. So fuck you! (And fuck her too!)

Every music genre needs its “Take This Job and Shove It,” and thus this 1990 anthem from North Carolina indie-rock lifers Superchunk became the protest song for Kinko’s dead-enders in college towns nationwide who dreamed of flipping off their lazy bosses so they could devote time to their Pixies-influenced sock-puppet troupe. The competition is heated, but “I’m working / But I’m not working for you! / Slack motherfucker!” could be the best use of the sweariest of swear words in a song.

Parents: If you happen upon your angelic, adorable five-year-old singing, “This is fucking awesome,” blame Macklemore. And if you’re not a parent, well, fuck that guy anyhow.

In this early punk classic, singer Chrissie Hynde has the hots for some rock stud, and the feeling is entirely mutual. She likes the way he crosses the street; he bruises her hip in bed; they have sex all over Cleveland, etc. Finally, as the song peaks, she decides it’s time to bail: “Trapped in a world that they never made / But not me baby / I’m too precious / I had to fuck off.” Except she swallows “I had to,” and so what you hear is Hynde spitting “fuck off” at her fuck buddy with the same ferocity Johnny Rotten reserved for the queen of England.

Twenty-something Oberlin graduate Phair wakes up in yet another rando’s bed, more bummed than angry with herself, more exasperated than enraged with the man-child next to her. “I can feel it in my bones / I’m gonna spend another year alone,” goes the weary bridge, and then the pickax chorus: “It’s fuck and run, fuck and run / Even when I was 17 / Fuck and run, fuck and run / Even when I was 12.” It’s an acute depiction of the despair that sometimes accompanies freedom, and it’s as hummable as a Subway commercial.

Thanks to her multifaceted use of the C word on her staggering debut single, fans of this Harlem rapper, à la Justin Bieber’s Beliebers, have taken to calling themselves Kunts. (Kool!) At the end of the first verse, Banks brags that she’s so fine even your straight girlfriend will want to “lick my plum.” “I guess that cunt getting eaten,” she repeats four times, in case you missed it the first three. Later, she taunts her competitors (Nicki Minaj?): “Who are you, bitch, new lunch? / I’m-a ruin you, cunt.” Pro Tip to the Fellas, Part 2: Forget what you just read, and never, ever speak this word in any context. (Exception: drunken Scotsmen. Then it’s funny.)

It’s hard as fuck to pick only one Prince song. We could have gone with “Sexy M.F.,” “Erotic City,” even “Irresistible Bitch.” In “Let’s Pretend We’re Married,” a frisky New Wave dance tune from the album 1999, a guy who’s been dumped spots a single lady named Marsha and tries to seduce her with frankness and humor. “I’m not saying this just to be nasty / I sincerely wanna fuck the taste outta your mouth,” Prince hisses. A song so filthy, Eddie Murphy turned it off when he drove his Porsche 928 past St. Patrick’s Cathedral in 1983.

When you name your San Francisco–based punk band Dead Kennedys, releasing a single called “Too Drunk to Fuck” is no biggie. In 1981 the song remarkably reached the Top 40 on the U.K. singles chart; in listings the title was excised to “Too Drunk To.” (To what? Gob?) Best couplet: “You give me head / It makes it worse / Take out your fuckin’ retainer / Put it in your purse.”

Let’s face it: Cursing is inarticulate. Humans have been speaking for at least 10,000 years, and when angered the best response we can compose is “Fuck you”? The grim rap-rock band Korn hinted at this paradox in its hilarious 2003 song “Y’all Want a Single,” a petulant reply to its record label’s request for a hit song. Jonathan Davis, who worked as a mortician before he was a singer, shouts, “Fuuuck that, fuuuck that,” over and over, tallying 89 fucks in the song, an average of one every 2.2 seconds.

Rap’s three greatest diss songs are Jay Z’s “Takeover,” Nas’s “Ether” and Tupac’s “Hit ’Em Up.” Jay Z’s attack on Nas is methodical, rooted in the accusation that he’d made only one great album, Illmatic. In reply, Nas bundles a series of taunts at Jay Z: He calls him ugly and a sellout and dubs him Gay-Z (this was before Jay was on it with Beyoncé). But these are Hallmark friendship cards compared with the Tupac song, which is vicious and unrelenting, the Keyser Söze of diss songs. Pac insults Biggie Smalls (“I fucked your bitch, you fat motherfucker”) and everyone in his orbit, including Puff Daddy and Lil’ Kim. Pac’s flames ignited the East Coast–West Coast rap wars, which culminated in his and Biggie’s murders.

Cursing: It’s fucking fun! Just ask the loutish English punk group Anti-Nowhere League, who must have pissed their bondage jeans recording this 1981 seven-inch B-side: “And I fucked a sheep / And I fucked a goat / I’ve had my cock right down its throat / So what.” Ironically, “So What” became the band’s meal ticket when metal superstars Metallica covered it on their Garage Inc. album. “Metallica bought me a Harley,” said lead singer Nick “Animal” Culmer.

From the same New York antiwar freaks who gave you the smash hits “Coca Cola Douche” and “Kill for Peace”—not to mention the lyric “I’m not ever gonna go to Vietnam / I prefer to stay right here and screw your mom”—comes this mocking folk-rock hootenanny that’s nearly the plot of a Jason Bourne movie. “Who can kill a general in his bed? / Overthrow dictators if they’re Red? / Fucking-a man! CIA man!” In the late 1960s the FBI described the Fugs’ debut album in an internal memo as “vulgar and repulsive.” Thanks for the compliment, J. Edgar Hoover!

When critics complained that South Park was nothing but fart jokes, co-creators Trey Parker and Matt Stone introduced Terrance and Phillip, whose cartoon show within the cartoon show revels in gas-based toilet humor. Early in Parker and Stone’s 1999 feature film South Park: Bigger, Longer & Uncut, the kids watch a Terrance and Phillip movie in which the duo quickly bursts into a faux–Broadway tune, “Uncle Fucka,” which begins, “Shut your fucking face, uncle fucka / You’re a cock-sucking, ass-licking uncle fucka.” Every adult in the theater leaves, but the boys remain seated, admiring (and soon imitating) this awesome display of filth. One of the songs from the movie was nominated for an Academy Award. It was not “Uncle Fucka.”

In December 1976 the Sex Pistols shocked a nation of prim, umbrella-carrying tea drinkers by swearing multiple times (a pair of shits and three fucks—a full house!) on a six P.M. TV news program. They were instantly on the front page of British newspapers, with headlines such as FURY AT FILTHY TV CHAT and FOUR-LETTER PUNK ROCK GROUP IN TV STORM. For their debut album they recorded “Bodies,” in which Johnny Rotten swears not for fun or outrage, like most singers, but at the horror of humanity. “Fuck this and fuck that / Fuck it all and fuck a fucking brat,” he hollers, making each fuck a percussive splat. SEX PISTOLS IN NEW ‘FOUR LETTER’ STORM, The Sun soon reported.

Faithfull was an English rose, the most gorgeous blonde in swinging London, with schoolgirl eyes, a sweet singing voice and Mick Jagger at her side. Then came heroin addiction, homelessness and a suicide attempt (via 150 sleeping pills). You can hear all that misery, plus about 5 million cigarettes, on her 1979 album, Broken English, which she has called an “exorcism.” A highlight is “Why’d Ya Do It,” a raging response to infidelity sung in a witchy voice two octaves below Lauren Bacall’s range. “Why’d ya let her suck your cock?” Faithfull demands. “Every time I see your dick, I see her cunt in my bed.” When she first sang it onstage, to people who remembered her as an innocent, they were “absolutely staggered,” she said. “I’d see people’s jaws dropping.” Yours might too.

Elmer Valentine, co-founder of Whisky a Go Go, the L.A. club where the Doors got their start, said of Jim Morrison, “He was kind of ahead of his time on certain things—like swearing.” Indeed, Morrison was a proud troublemaker and button-pusher, as well as a drunk, which combined to make him the William Shakespeare of cussing singers—most notoriously in “The End,” an oedipal melodrama that climaxes with Morrison telling his father, “I want to kill you,” then saying to his mother, “I want to fuck you.” The first time the Doors played “The End” at the Whisky, they were fired. In 1967, when Morrison’s kindly mother, Clara, came to see the Doors at a show in Washington, D.C., he screamed his illicit urge, then looked at his mom, who stood on the side of the stage, stunned. We get it, Jim. You’re a rebel.

When “Killing in the Name” became an unlikely U.K. hit in late 2009, the BBC invited Rage Against the Machine—an American hard-rock band notorious for its contempt for authority—to play it live on a breakfast show, politely requesting that Rage omit the “Fuck you, I won’t do what you tell me” refrain. Defying the network, vocalist Zack de la Rocha fired off four fucks, causing millions of Brits to gag on their scones before the host shouted, “Get rid of it,” and a BBC engineer faded out the performance. In effect, Rage had told the BBC, “Fuck you, I won’t do what you tell me.” Who was surprised by that outcome?

The song, written by longtime Playboy contributor Shel Silverstein, tells the story of a guy who “grew up mean” because he was taunted for having a girl’s name. He vows to kill the dad who named him Sue, and the song culminates in a bloody barroom brawl between the two. When Cash debuted “Sue” at San Quentin State Prison in 1969, the inmates roared. It then topped the country chart for five weeks—though only after Cash’s record company bleeped out “son of a bitch” and “damn.” In 1979 singer Carlene Carter described herself to a New York audience as “the gal who put the ‘cunt’ in country.” She didn’t know her stepdad, Johnny Cash, had flown to New York City to surprise her. “My dad didn’t speak to me for about a year,” she said. Kinda hypocritical, no?