Pop culture obsessives writing for the pop culture obsessed.
Pop culture obsessives writing for the pop culture obsessed.
Illustration for article titled Sad trombone: 18 songs about awkward sexual encounters

1. Flight Of The Conchords, “Business Time” (2008)
Few things make sex as bad as a partner who isn’t paying attention to subtle signals, like the other participant saying “Eh, I think I’m just going to go to sleep. I have to work in the morning.” In Flight Of The Conchords’ straight-faced comedy song “Business Time,” Jemaine Clement takes on the character of one such oblivious partner, who’s mighty damn proud of his sexin’ skills, and doesn’t realize his boasts about his prowess and the weekly “business time” ritual (scheduled for Wednesdays, because “conditions are perfect / there’s nothing good on TV”) are erotic Kryptonite. Like when he counts brushing his teeth as foreplay. Or when he tries to take his pants off and trips over them because he hasn’t taken his shoes off yet. Or when he finally gets down to nothing but socks, and takes a moment to appreciate himself. (As Coupling taught us, “No self-respecting woman will ever let a naked man in socks do the squelchy with her.”) Finally, he gets down to business time itself, crooning, “Making love / making love for two / making love for twoooo minutes / When it’s with me, you only need two minutes / ’cause I’m so intense.” Two minutes later, “business hours are over,” and he lets his disbelieving partner know he isn’t surprised she wants more of him. Unfortunately, he’s so terribly tired. Then again, why exactly would she want more of that?

2. Randy Newman, “Maybe I’m Doing It Wrong” (1971)
From the Southern-gothic touches on Good Old Boys (featuring a nude exhibitionist purse snatcher and a hillbilly whose wedding night is spoiled when his unadoring bride “laughs at my mighty sword”) to the crooning “I Want You To Hurt Like I Do,” Randy Newman has created enough sexually and emotionally dysfunctional protagonists to populate his own clinic, and he once composed an anthem for them. “Maybe I’m Doing It Wrong” is a fumbler’s lament in which the singer struggles to find something in himself worthy of credit: “Sometimes I throw off a good one / At least I think it is / No, I know it is / But I shouldn’t be thinking at all.” Perhaps sensing that the number might be a little too on-the-nose, Newman originally released it on his little-heard 1971 live album; a studio version didn’t surface until more than 30 years later, when it appeared as a bonus track on a Rhino reissue of Sail Away.


Randy Newman - Maybe I'm Doing It Wrong [Studio Version] from Maldoon on Vimeo.

3. Elvis Costello, “New Lace Sleeves” (1981)
In the liner notes to the Rhino reissue of his 1981 album Trust, Elvis Costello describes “New Lace Sleeves” as being about “the tension between passion and the emotionally suppressing influence of ‘being civilised,’” which is evident in the song’s lines about “socialite sisters” whose fingers have “never seen working blisters,” and in all its references to the myth of British exceptionalism. But the theme of the song is best expressed in its opening verse, in which Costello describes “bad lovers” waking up next to each other and remembering how their fun flirtation at the start of the night turned into tedious, perfunctory boning. Costello expresses the distance between a sexy image and awkward reality when he sings, “Good manners and bad breath will get you nowhere.”

4. Richard Thompson, “Read About Love” (1991)
The lead cut from Thompson’s 1991 album Rumor And Sigh is a heartfelt plea for the importance of proper sex education. Thompson being Thompson, he makes his argument by vividly imagining just how fucked-up a person denied proper sex education could get. The singer relates how, when he was a child, parents and teachers shut him down when he asked them “what love really means,” so he was forced to seek out information from other sources: He “read about love” in such magazines as Cosmopolitan, Seventeen, and Hustler, as well as in a book “written by a doctor with a German name.” At the end, it turns out that he’s reciting this litany to assure the woman weeping in his bed that he truly understands “the ways of a woman,” and “if something’s wrong, then it must be you.” After all, “When I touch you there, it’s supposed to feel nice / That’s what it said in ‘Reader’s Advice’.”

5. Loretta Lynn, “When The Tingle Becomes A Chill” 
Time was, most country songs tended to be about people wishing they could go to bed with someone they can’t, or regretting (or celebrating) going to bed with someone they shouldn’t. A year after scandalizing conservative country listeners with her 1975 hit “The Pill,” a rollicking tribute to the fun of having sex without the threat of adding another critter to the litter, Loretta stirred the pot again with this shockingly frank song (written by Lola Jean Dillon) about being obligated to have joyless sex out of a sense of marital duty, and smile about it. Lying next to her sleeping, contented husband, the wife softly cries to herself and confesses that “Although I pretend / You just don’t turn me on / The body performs / But the soul has no will.” She doesn’t see any light at the end of the tunnel, either: The woman clearly can’t imagine any way out of her marriage to a man she no longer loves or desires, so for her, nights like this are now just “part of the deal.”

6. Kid Creole & The Coconuts, “Mr. Softee” (1980)
In his guise as Kid Creole, August Darnell always comes on as the ultimate Latin lover and super-smoothie, potent and self-assured, but he’s enough of a comedian to constantly undercut that pose. And when he doesn’t, his Coconuts are more than happy to pitch in. Ever observant, the Kid notes he has “a funny feeling, baby, that tonight you want to sleep with me,” but it’s just that he has a lot of important work to do, and he has to get up early in the morning, so just this once, he has to be the strong one for them both and struggle to keep a lid on his fiery passions. The girls ain’t having it: “You’re a softee,” they taunt, “and hardly my type.” The Kid gets another funny feeling, that they may be implying something that can’t possibly be true. He tries to speak up for himself, but might be better off just keeping his mouth shut and sulking. “Don’t try to make an issue,” he warns, “about something that’s as small as this.”

7. The Lonely Island (featuring Akon), “I Just Had Sex” (2011)
“I Just Had Sex” might be the most triumphant song about the lamest instance of coitus ever put to music—not that the members of The Lonely Island seem to care. While Andy Samberg and Jorma Taccone rap rhapsodic about the girls who “let us flop around on top of them,” the details they boast tell a different story: She kept looking at her watch, he cried the whole time (while wearing his chain and turtleneck sweater), and the whole thing lasted 30 seconds. In spite of all that, The Lonely Island guys seem thrilled with the outcome, even though “she put a bag on my head” and “she might’ve been a racist.” Then again, as established on the opening track of 2011’s Turtleneck And Chain, the objects of the guys’ affections have reason to be unimpressed: “We’re Back!” details the many shortcomings of the collective junk of The Lonely Island, from unimpressive size to offensive odor to the fact that it’s soft as a melting stick of butter. Thankfully, as “I Just Had Sex” proves, even the most awkward of sexual encounters with the most repulsive of dicks can be rendered mind-blowing through the application of an incredible Akon hook.

8. Mel McDaniel, “Stand Up”  (1985)
The late country singer Mel McDaniel was renowned for the upbeat good cheer of his songs and persona, and his biggest hit treats even sexual humiliation as material for comradely barroom braggadocio. His message to the crybabies bemoaning their sad romantic fates all over the control dial is, get a grip, we’ve all been there: Can you top this one? And while there are a lot of guys who, once the wounds have scabbed over, might make a joke about the time they spent the night buying drinks for a woman who went home with the bartender, it takes a real man to sheepishly recollect the time he was crowing over his sexual prowess and about to roll over and go to sleep when the woman informed him that “she rated me a zero, said, ‘Honey child, you ain’t through.’”

9. Faces, “You’re So Rude” (1971)
This jaunty number by the ultimate good-time British band tells the classic adolescent one-that-got-away story. Sweet-talking as best he can, the hero coaxes the object of his affections back to his house, telling her how much his mother is looking forward to seeing her again, how taken the whole family is with her “low-cut frock,” “bird’s-nest hair,” and “stiletto heels.” But the house is empty; the hero forgot that the whole crew would be away visiting Auntie Renee. The lucky little bastard persuades her to start disrobing and settle down on the couch, only to panic and start shouting instructions for the girl to pull herself together (“You’re really looking a mess!”) when the family unexpectedly returns home early. Much of the song’s charm derives from the shambling, practically spoken-word delivery by Ronnie Lane, taking over from usual Faces vocalist Rod Stewart, presumably because Rod would have kept his cool and seen things through to the end even if Auntie Renee were sitting on the other end of the couch.

10. Was (Not Was), “Earth To Doris” (1988)
The worst part of really bad sex may be when the morning after comes and the participants are horrified to discover they haven’t died in their sleep. This one captures the essence of post-coital revulsion in just under two minutes of rant and noise. In a voice that sounds as if it crawled out of a sewer, David Was recounts meeting Doris at the Lovesick Motel and Restaurant: “She kissed me like she was hungry,” he says with a shrug, “so we got a room.” In the “cold, dim fluorescent morning,” she resembles a horse and is “making champagne out of 7-Up and cheap wine” while sitting “next to one of those insect electric chairs, her skin gleaming blue every time a fly died.” While he talks, the band pounds out a beat that sounds like a tango for two mismatched species of animals that are anatomically incapable of having sex, but too drunk and horny to keep themselves from trying.

11. Art Brut, “Rusted Guns Of Milan” (2005)
Art Brut’s Eddie Argos has never tried to present himself as a macho guy, never less so than on this song from the band’s debut in which he tries, and fails, to make love to his partner, then offers explanations and apologies in place of sex before deciding that maybe a warm beverage is the best he can do. “I’m so sorry, can I get you a cup of coffee?”, he sings, promising it will never happen again. Sadly, by the end of the song, that sounds like a likely story.

12. Kings Of Leon, “Soft” (2005)
The members of Kings Of Leon, on the other hand, practically ooze testosterone (and Jack Daniels, but that’s another story). But the protagonist of “Soft” doesn’t have any more luck than Argos, informing a would-be lover he’s “passed out in your garden / I’m in, I can’t get off.” Why? Well, look at the song title.

13. David Bowie, “Young Americans” (1975)
At least impotence doesn’t raise expectations only to let them down. In a few discreet lines, David Bowie’s “Young Americans” sums up the disappointment of lovers who can’t make it last. “It took him minutes, took her nowhere,” he sings before adding that her expectations weren’t even that high: “Heaven knows she would have taken anything.” It sets the scene for song about the anxieties of peaking too early. “We live for just these 20 years,” Bowie later asks. “Do we have to die for the 50 more?” The song provides no answers, but its exuberance sounds a defiant “no.”

14. J-Zone, “The Trojan War” (2002)
Bad sex can happen under the best circumstances, but when J-Zone straps on a condom in “The Trojan War,” sexual trauma is all but guaranteed as the irreverent rapper/producer fights a losing battle to maintain sensation, sensitivity, and a healthy blood flow while being strangled in latex. The disgusted anti-hero is so discouraged, he swears off condoms altogether until his angry sentient penis (voiced by Huggy Bear) develops a voice and mind of its own to warn its undiscriminating owner of the dangers of unprotected sex. Whether safe or unsafe, sex is a hassle in “The Trojan War.” It’s enough to make celibacy look appealing.

15. Frightened Rabbit, “Keep Yourself Warm” (2008)
Frightened Rabbit’s best song—which the Scottish band frequently uses as an encore—is sort of a paean to true love wrapped up in a sad story about the futility of anonymous sex. The key line in describing the encounter in “Keep Yourself Warm” goes, “I’m drunk, I’m drunk / And you’re probably on pills / If we’ve both got the same diseases / It’s irrelevant, girl.” The song, from the euphemistically titled The Midnight Organ Fight, goes on to declare, “you won’t find love in a hole.” So at least our narrator learned something important from his loveless, debauched evenings.

16-17. Lily Allen, “Not Fair” (2009)/ “Not Big”  (2006)
Lily Allen has always been direct with her lyrics (see “Fuck You”), and in "Not Fair," she pulls no punches in describing a (presumably former) lover who’s absolutely fabulous in every way—except in the sack. He’s a premature ejaculator (“you make this noise and it’s apparent it’s all over”) who leaves her sitting in a “wet patch in the middle of the bed.” It’s a perfect companion to Allen’s “Not Big,” which describes another lover who is poorly endowed. In that song, she gleefully sings, “You’ve only got yourself to blame / I’m gonna tell the world you’re rubbish in bed.” Her lover in that case is another premature ejaculator, when he can even give it up—or is she just making all this gossip up to get back at the guy who dumped her? It can be read either way, but either way, it’s clear the sex wasn’t working out.

18. Elastica, “Stutter” (1995)
Elastica’s first single (and only real hit) was this fantastic outburst about a male friend who fails to satisfy. Singer Justine Frischmann runs through her man’s litany of excuses for not wanting sex—he’s drunk, he’s looking for something specific, does he have another woman?—and ultimately ends in her own frustration (“I really want you to,” she pleads). But she’ll get no relief from this one, even though she appears to possess Dan Savage’s three most important “G” traits: She’s good, giving, and game. It’s probably too late, but obviously she should DTMFA.

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