1. Jack and Diane, John Cougar Mellencamp, “Jack & Diane”

The quintessential “little ditty” about two crazy kids in love, John Cougar Mellencamp’s “Jack & Diane” introduces us to a pair of all-American teens with all-American dreams. “Jackie’s gonna be a football star” with Diane the pliant debutante at his side, forever willing to let him have his way with her behind whatever Tastee Freez they encounter on life’s long road. But is she? There’s already hints of discord—Jack wants to run off to the big city, Diane doesn’t really see the point—and their future happiness seems to hinge not only on Jack making it into the NFL (Good luck!), but on maintaining the casual thrill of teenage invincibility. As Mellencamp reminds and/or begs, they have to “hold on to 16 as long as you can,” before adulthood comes along with its big changes, and its demands of something more than pipe dreams and chili dogs. Oh yeah, life goes on. [Sean O’Neal]

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2. Johnny and Mary, Robert Palmer, “Johnny And Mary”

A portrait of a strained relationship in media res, Robert Palmer’s “Johnny And Mary” catches up to the couple right as things have reached their lowest ebb, and just as both have become utterly resigned to it. Johnny’s looking for “all the world to confirm that he ain’t lonely,” whether he’s “running around” on Mary in the traditional sense, or just constantly looking for reassurance everywhere but in his marriage. Either way, his attention is elsewhere, leaving an unhappy Mary to ponder how she settled for a life that leaves her so unsatisfied, all while sighing that “she should be used to it.” But the question is how long she’ll put up with it: Their arguments always seem to reach dead ends, as Johnny remains convinced he deserves more and there’s no sense in talking about it. But if Mary ever does get fed up with constantly hedging her bets, it seems pretty likely Johnny will soon be doing his “running around” with no one waiting at home. [Sean O’Neal]

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3. Brenda and Eddie, Billy Joel, “Scenes From An Italian Restaurant”

The story of Brenda and Eddie could be that of John Cougar Mellencamp’s “Jack And Diane,” picked up 20 years later. The former prom king and queen get married and “live for a while in a very nice style,” until the crushing realities of life and Sears waterbed bills get in the way. But even after their messy divorce—even after they find new spouses, new jobs, and new lives, and lost touch for a while—these two who “parted the closest of friends” obviously still care for each other. Otherwise, why would Eddie offer Brenda this standing dinner date invitation to their favorite Italian restaurant, where the wine and the reminiscing over their good ol’ days still flow freely. Even our narrator Billy Joel doesn’t seem to know what will happen: “That’s all I heard about Brenda and Eddie / Can’t tell you more than I told you already,” he swears. But he’s strongly hinting there’s still a spark there, just waiting to be rekindled over a good bottle of rosé. [Sean O’Neal]

4. Penny and Jack, The Essex Green, “Penny And Jack”

The conflict at the center of The Essex Green’s “Penny And Jack” isn’t especially complex, but like a lot of petty fights between people in a relationship, it hints at a much deeper issue. Jack and Penny live in New York, where Penny is “always having a good time.” Jack, however, would prefer to “be in another town.” New York isn’t gloomy enough for him, so he’d rather live somewhere “where it’s cloudy but where he can lay down.” No offense to Jack, but that’s a lousy attitude. Not to mention, it sounds like Jack’s problem is more with Penny than it is with New York. The fact that Jack is miserable while Penny is having the time of her life certainly doesn’t suggest a relationship that’s built to last. Hopefully, she’ll dump his grumpy ass and just enjoy the city on her own. [Sam Barsanti]

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5. Romeo and Juliet, Dire Straits, “Romeo And Juliet”

Dire Straits’ “Romeo And Juliet” invokes the name of William Shakespeare’s tragic tale of young love, but the heartache here comes in the form of Juliet (a stand-in for Holly Vincent, of Holly And The Italians) leaving her Romeo (Dire Straits frontman Mark Knopfler) for the limelight. Romeo laments a time when their passion was so intense, his Juliet would cry when they made love. But once Juliet got her big dream—with Romeo’s help, no less—suddenly she’s all, “Oh Romeo, yeah, you know I used to have a scene with him.” Unlike in Shakespeare’s play or even its fellow big-city update, West Side Story (which gets a shout-out), this Romeo and Juliet don’t get to love each other to their deaths. In fact, their love might not even be as real as Romeo believed. But while Romeo is out looking for a new Juliet on the street corners, seemingly destined to repeat the same doomed relationship over and over, he’s obviously still carrying a torch—and forever asking, “When you gonna realize it was just that the time was wrong, Juliet?” [LaToya Ferguson]

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6. Ellen and Ben, The Dismemberment Plan, “Ellen And Ben”

The relationship at the center of The Dismemberment Plan’s “Ellen And Ben” isn’t happening now or even to the narrator. It’s already happened around him, beginning when he first witnessed Ellen and Ben meet at a party and make a date, even though they didn’t seem to like each other. Next thing he knows, they’re not even bothering to put on clothes when he comes over to pick up his borrowed copy of Nebraska. Inevitably, the song’s storyteller gets a little sidetracked by his own life, only to hear secondhand that Ellen and Ben “broke up loudly at a wedding”—a strange ending, he thinks, considering they were once so passionate they “made each other feel like they could die, but they couldn’t stay the slightest of friends.” Still, given the intensity of those feelings, get those two together at another wedding, and it sounds like there’s a good chance Ellen and Ben will have a passionate reunion. [Jesse Hassenger]

7. Zak and Sara, Ben Folds, “Zak And Sara”

At first, the couple of Ben Folds’ “Zak And Sara” seem to be having your typical relationship problems: “Sara (spelled without an ‘h’) was getting bored” while “Zak (without a ‘c’)” spent his time messing around with some new guitars. So far, so basic—and then listeners find out that Sara appears to have the gift of clairvoyance. Sara’s predictions turn increasingly dark as Folds’ piano licks remain whimsical, even as it becomes clear that Zak is getting startled, too. As Sara shares her visions of families drowning in their cars, Zak tries to soothe her with layaway plans and playing her favorite song. In other words, he has no freaking clue what to do with her. There’s no indication by the end of the song what exactly will happen to them, but there’s a good chance Sara already knows—and that Zak’s song probably isn’t going to placate her forever. [Caroline Framke]

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8. Tommy and Katie, Trisha Yearwood, “She’s In Love With The Boy”

Country music is forever balanced on the uncertainty of middle America. It’s a good place, full of homespun values and wisdom passed down from the elders. It’s also a place ravaged by alcoholism, cheating, and desperately expressed emotions. Trisha Yearwood’s “She’s In Love With The Boy” fully embraces both potential fates. The song itself is giddy with the prospect of young love in its tale of Katie and Tommy, who cling to each other desperately despite her father’s antipathy. Being as they’re teenagers, Tommy proposes to Katie with his class ring until he can scrounge up something more, while Katie’s mother assuages her upset husband by pointing out how Katie looks at Tommy like she still looks at him. Anecdotal evidence aside, the song repeatedly intones that the two will get married “even if they have to run away”—which isn’t exactly a strong foundation for lifelong bliss. Katie may look at Tommy with love now, but perhaps that’s just because she doesn’t know that 48 percent of teen marriages end in divorce within 10 years. [Libby Hill]

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9. Spanish Johnny and Puerto Rican Jane, Bruce Springsteen, “Incident On 57th Street”

Spanish Johnny and Puerto Rican Jane have an uphill battle to fight when it comes to their love. Namely, Spanish Johnny is a criminal no one trusts—certainly not the hard girls on Easy Street, and especially not the pimps. As a result, the threat of death and arrest hang forever around their relationship, which doesn’t especially bode well for its future. So when Johnny leaves Jane at the end of “Incident On 57th Street,” unable to resist the lure of the streets and “easy money,” his promise to meet her tomorrow night on Lover’s Lane ends in a “maybe.” And that “maybe” is left forever hanging in doubt. [Molly Eichel]

10. Tommy and Gina, Bon Jovi, “Livin’ On A Prayer”

Tommy’s an unemployed dockworker, Gina’s a diner waitress—but money doesn’t matter in the long run. At least, that’s what the chorus of Bon Jovi’s “Livin’ On A Prayer” swears on repeat: “They’ve got each other and that’s a lot,” it says. Still, these two sure spend a lot of time assuring each other of that, with first Gina telling Tommy about the redeeming power of love, then Tommy calming Gina by telling her everything’s going to be okay. Meanwhile, that empty talk is covering a lot of unspoken realities and broken dreams, like Tommy’s pawned guitar and Gina’s unfulfilled desires to escape. As far as “Livin’ On A Prayer” is concerned, that shared burden is the bedrock of any lasting couple. Still, they’re only halfway there. [Molly Eichel]

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11. Judy and Johnny, Lesley Gore, “It’s My Party”/“Judy’s Turn To Cry”

In Lesley Gore’s 1963 hit, “It’s My Party,” she declares she’ll cry if she wants to—as after all, her ex-boyfriend Johnny showed up with new girlfriend Judy on his arm. There’s no question as to what happens to Johnny and Judy: Gore released the sequel “Judy’s Turn To Cry” later that year, revealing she’d won Johnny back from that hussy. Is theirs a love for the ages? Given how quick Johnny is to pinball back and forth between these two girls, it’s probably only a matter of time before he’s caught up with Judy again—or Julie, or Janie, or Jodi—and those tears start flowing anew. But hopefully before that happens, the brokenhearted party girl has enough self-respect to walk away with her dignity intact, perhaps while singing Gore’s next big hit, “You Don’t Own Me.” [Mike Vago]