Is the Ultimate Summer Bop Happy or Sad? Welcome to Jezebel’s Song of the Summer Tournament

Song of the Summer discourse is a cherished internet tradition. Every year, people assess the crop of pop singles in an attempt to determine which will define that summer. For our part this year, Jezebel is holding a tournament voted on by our readers. Instead of focusing on “the song of the summer,” a specific distinction that is technically reserved for only one song (in the U.S., that which has the biggest chart impact), we looked at Billboard’s mega-list of the Top 10 most popular songs in the U.S. for every summer from 1990 to 2022. From there, we selected 16 songs that have, in our estimation, endured or left an indelible impact on pop. More importantly, most of these are songs that we love (and still, after decades in some cases, want to hear).

Most people probably associate summer songs with something uptempo, light, and breezy, but a number of summer hits are on the slow and/or sad side. In fact, there’s a surprising market for songs about being sad in the summer or at least reflect that idea in the title: Lana del Rey’s early hit “Summertime Sadness” (her first U.S. Top 10—courtesy of a remix), Taylor Swift fan favorite “Cruel Summer,” and Maisie Peters’ “sad girl summer.” The fact is that not everyone’s moods sync with the seasons, and an artist who can manage a summer banger (whether uptempo or down) about negative affectation deserves a shout.

We’ve set up this tournament to culminate in a face-off between the highest-voted fast/happy and slow/sad songs. Here’s how it works: In this post, the 16 songs are paired according to their genre grouping: Vote on your favorite from each pair (polls are at the bottom of each slide.) The winners will, bracket-style, be back next week to face off. Out of those votes, four will survive. The following week, they’ll battle and we’ll be left with the top-voted fast/happy summer song, and the top-voted slow/sad summer song. In the final week, we’ll set them against each other to finally determine, once and for all, if the Ultimate Song of the Summer is fast&happy or slow&sad. Get to voting.

In a kind of inadvertent celebration of Christmas in July, Roxette’s “It Must Have Been Love”—originally written as a holiday song and released in 1987 in the group’s native Sweden—was slightly tweaked and reissued for the soundtrack of the 1990 blockbuster Pretty Woman. That movie had a long shelf life (it spent 16 weeks in the U.S. Top 10 after its March 23, 1990 release), and its soundtrack spawned a few hits, including Roxette’s and Go West’s “King of Wishful Thinking.” Lyrically, the pop duo left some frost around the edges (“Leave the winter on the ground”; “It’s a hard winter’s day…”), but Marie Fredriksson’s increasingly impassioned vocal delivery brings the heat. Her ad-libs at the end, including what sounds like an impromptu key change, are as astounding today as they were 33 summers ago. The production, with its big hollow drums and piano/synth tête-à-tête in the break, is the stuff of pure early ‘90s power balladry—emphasis on the power.

There’s a macro and a micro meaning to this chart-topper from Harry Styles’ third solo album, Harry’s House. On first listen, Styles sounds as if he’s feeling sorry for himself about the loss of a former lover, lingering on the specific—yet universal—loneliness that settles in upon the realization that he’s the only one still singing about their relationship’s end: “Seems you cannot be replaced/And I’m the one who will stay.” Hear that chorus a few hundred times, however, and it plays like a melancholy meditation on aging amidst a rapidly decaying world to the beat of 80's-era synth. It’s certainly not the saddest song, but no one’s confusing it with an optimistic little ditty either. No, things are not the same as they were. Someone with two degrees can no longer own a home or retire honorably in the United States.

Drums please!

“Summertime” is the estival counterpart to “All I Want for Christmas Is You”—a perennial jam whose fleeting presence is an essential signifier of the season. In fact, with all due respect to Memorial Day, I don’t consider it to be officially unofficially summer until I hear “Summertime” (this year, it happened one sunny Sunday in May on the way to Prospect Park). It’s based on a sample of Kool & the Gang’s “Summer Madness,” a psychedelic instrumental whose haze and ascending melody capture the feeling of hot air in sound. Will Smith’s summertime imagery—basketball courts, double-dutch, a barbecue—is familiar enough to be universal but specific enough to paint a vivid picture. “And as I think back makes me wonder how/The smell from a grill could spark up nostalgia,” he raps. And now his song itself lives among those hallmarks of summertime nostalgia.

What’s left to say about the song that altered the internet—and bachelorette parties—forever? From the outset, WAP wielded so much power that it inspired the great moral panic and conservative crusade of 2020. It didn’t just sit at the top of Billboard’s Hot 100 for weeks—it made history as the first female rap collaboration to debut at number one. Sampling Frank Ski (“There’s some whores in this house” can be heard exactly 79 times from start to finish), and featuring truly Shakespearean lyrics (My head game is fire, punani Dasani/It’s going in dry, and it’s coming out soggy) the bawdy bop was just what the internet needed in the midst of a frightening, frustrating pandemic. It was fun to sing (poorly), fun to dance to (again, poorly), and fun to watch people lose their ever-loving minds over. This may sound dramatic, but WAP did more to save lives than the U.S. government, simply by providing housebound people with a filthy good time.

The infatuation described in “Weak”—losing control, being in a daze, a heart racing in triple time (dangerous, but we’ve been there), and of course, getting weak in the knees—sets spring fever to music. And, indeed, the single’s crawl to the top of the charts began when it was released on April 16, 1993—eventually dislodging Janet Jackson’s megahit “That’s the Way Love Goes” from the top of the charts to finally hit No. 1 that July, and has since proven to be one of the defining ballads of ‘90s R&B. You’d be hard pressed to find one as sweet—though as was the case for most of the New York-based trio’s output, there’s still a bit of edge here. Lead singer Coko’s limber voice has a distinct, piercing tone, the keyboard that opens the song sounds like something that could have been purchased at Radio Shack, and you can hear the air moving in the stripped-down track, endowing it with a sense of humidity. “I had written this song love song ‘Weak’ for Charlie Wilson, but I gave it to them,” writer/producer Brian Alexander Morgan recalled to Rolling Stone in 2015. “Coko was real cold to me at first and not very nice. She didn’t like the song and gave me real attitude when we recorded it.” You can’t hear it at all on the record. A consummate professional.

You might think you know the full story of Wiz Khalifa and Charlie Puth’s “See You Again.” As it turns out, there’s a lesser-known source of inspiration behind its sentimental lyrics in salute of the family you’re born with, and the one you make along the highway of life. Yes, it was written to commemorate the unexpected loss of Paul Walker and his premature departure from the Fast & Furious franchise in the seventh film (an indisputable summer blockbuster). However, both Puth and Wiz Khalifa recently revealed there were different deaths they had in mind when co-writing the song. For Puth, it was a dear friend who’d died in a car crash, and for Khalifa, the passing of his sister who identified as transgender.

“At the time I was writing “See You Again” is when she got sick,” the rapper said in 2022. “I knew I was pretty much going to be letting go…I think it was able to touch anybody who was going through a loss, or could be dealing with a situation. That is what made it so special to me.”

“How can we not talk about family when family’s all that we got?” takes on an even deeper meaning if you happened to be listening to it as you sat amongst your own in the summer of 2015—likely biting your tongue as they debated the possibility of a Trump presidency. Now try not to get even more choked up at Furious 7's final scene.

Superstar DJ Honey Dijon says that there are a handful of songs that are failsafe crowd-movers. Among them: “Finally” by CeCe Peniston, “Gypsy Woman (She’s Homeless)” by Crystal Waters, and “Show Me Love” by Robin S. Thirty years after the release of the Stonebridge remix that would go on to become the definitive version of “Show Me Love,” the song remains an intense experience—time has done nothing to erode the impact of Robin S’s soaring vocal, those pummeling beats, the grinding bass line, or the Korg M1 organ preset that would become the song’s signature sound. When Beyoncé dropped “Break My Soul” in 2022, many noticed similarities to “Show Me Love” (via that organ sound) and she even listed the writers of “Love” in the credits of “Soul” for her song’s use of “elements” from Robin S’s original. There are club classics that represent the time in which they were first released and consumed brilliantly, little time machines with insistent pulses. But then there are songs like “Show Me Love” that transcend time altogether.

Ah, “Despacito,” otherwise known as the song that impelled innumerable sweaty white male twenty-somethings to slur something resembling Spanish into the ears of young women in bars and clubs across the country. If you were there, you remember. You might also be entitled to compensation.

Did those individuals know what they were singing? Certainly not. Was the dance floor filled with white people attempting to unhinge their hips each and every time it came on? Absolutely. “Despacito,” in all of its lilting acoustic guitar glory, was such an instant earworm that if you closed your eyes just tight enough, “Ben” with the hot beer breath became a guy that actually knew what he was saying. Then, Justin Bieber came along, remixed it, and he, too, became a guy that...vaguely knew what he was saying. Who could blame them? It’s too fun not to *attempt* to sing along with. Let’s remember some of its lyrics:

I want to breathe in your neck slowly

Let me murmur things in your ear

So that you remember if you’re not with me

Slowly

I want to undress you in kisses slowly

Firmly in the walls of your labyrinth

And of your body, I want to create a manuscript

Up, up, up, up

I want to see your hair dance

I want to be your rhythm

Want you to show my mouth

Your favorite places (Favorite, favorite baby)

Let me trespass your danger zones

Until I make you scream

And you forget your last name

Slowly

We’re gonna do it on a beach in Puerto Rico

Until the waves scream Oh Lord

So that my seal stays with you

Not many artists could sing “Let me trespass your danger zones” so, hats off to Luis Fonsi for being one of them.

Much has already been written about how P. Diddy (née Puff Daddy née Sean Combs) masterfully took a song about stalking and made it something that anyone grappling with a grief they knew no words for could sing along to. The Grammy-winning personal tribute to the Notorious B.I.G. is made all the more heart-rending due in part to his estranged widow’s haunting vocals and its simple, still stirring, verses (notably, not written by close friend, P. Diddy): “What a life to take, what a bond to break/I’ll be missing you.”

Frankly, the latter fact is a bit of a bummer. Even still, the song had such resonance that it spent 11 weeks at the top of the Billboard Hot 100; reached No. 1 in 16 countries (including the U.S.); was anointed the best-performing single of 1997 in Iceland, Romania, and the Netherlands; and went on to become one of the best-selling singles of all time. It also managed to reach my own then-backyard of Napoleon, Ohio (population 9,175). After a classmate of my older sister’s passed away in a tragic car accident, the school choir performed it at his funeral.

In 2012, America had a summer fling with Australian singer-songwriter Gotye, whose Sting-ish “Somebody That I Used to Know” went to No. 1 on the Billboard Hot 100 for eight weeks. And then we never heard from him again, in true fling fashion. The song remains a weird vibe—I’ve never heard such seething accompanying a xylophone before or since—commercial ear candy that invites you to witness a kiss-off. Gotye wasn’t the first person to use “you’re just somebody that I used to know” as a way of diminishing a relationship (Elliott Smith’s 2000 album contained a similarly acidic song of the same title), but he was the one who was able to spin it into a pop smash. There’s something sunshiney about the chorus—especially the call-and-response “somebody”/“I used to know” on the fade out—but the portrait of a dead relationship and the resulting ire is pure rot.

Did you know that “Genie In A Bottle,” wasn’t just the iconic pop debut of Christina Aguilera? It’s actually an ode to self-respect? Well, in case you missed a then-18-year-old Aguilera’s press tour upon its release in 1999, it is.

“It’s a song about self-respect,” she told Good Morning America of the No. 1 hit. “People don’t get that. It really is, it really is. You’re saying, ‘You gotta treat me the right way.’…Don’t give your love away too easily.”

Critics—including fellow teen pop idol Debbie Gibson—had other interpretations but I always got what she was saying: You can’t expect just anyone to release you from a century of lonely nights. Sometimes, it pays to have a little patience. With great horniness comes great responsibility, etc., etc. When everyone else was wishing on any lover to rub them willy-nilly that summer, Christina demanded that anyone who finds her bottle do so the right way. And that, folks, is why Genie In A Bottle remains immortal.

What would come to be a foremost example of 21st-century bubblegum pop originally started out as a folk song. Had Carly Rae Jepsen decided to go with that original arrangement and not the dance-pop sparkler it became, the larger world might never have been blessed with her indelible tune. In aggregate, it’s sunshine in a song, a definitive component of the soundtrack of the summer of 2012. When “Call Me Maybe” broke in the spring of 2012, it spread with a virality more reserved for silly YouTube videos (or maybe Rebecca Black’s “Friday”). People passed it around amazed, as if they couldn’t believe such a song was possible. It’s still amazing.

In 2005, Mariah Carey launched one of the most head-spinning comebacks in pop history. She’d been written off after the flop of her quasi-biopic Glitter (2001) and the following year’s Charmbracelet album failed to turn up a single hit. Carey came off as undaunted and unbothered on 2005’s varied and lively The Emancipation of Mimi. On the album, in general, and its second single “We Belong Together” in particular, Carey seemed to build on past strengths and tailor them for mass appeal. The sing-songy emulation of Bone Thugs-N-Harmony’s collective flow that she evinced on 1997’s “Breakdown” is back in “Together,” whose first and second verses have entirely different melodies. The dynamism is electric, from Carey’s plaintive singing to the titanic knock of co-producer Jermaine Dupri’s beats. It all made “Together” the ultimate fast slow jam, a distinctly summery sadness.

Top 40 radio likely ruined “Rolling in the Deep” for you back in 2011, but long before it ever became relegated to dentist offices, it was a smart, scornful breakup ballad. Equal parts authoritative tell-off, and mournful declamation of what could’ve been, “Rolling in the Deep,” did what few pop songs (save for Beyoncé’s, “Best Thing I Never Had” and Christina Perri’s “Jar of Hearts”) of the summer managed to achieve: It gave the heartbroken something profoundly cathartic to belt with the windows down.

Its thumping drum beat, mounting percussion, and mega chorus might disguise it as a track for those who’ve made it to the other side of a devastating split. But the lyrics? Those could only be written—and deeply felt—by someone in the throes. Also, it’s rumored to have been inspired by a British musician known as, “Slinky Sunbeam.” Which, yeah...that’s pretty bleak, too. Based on the song’s success, however, it’s safe to say we’ve all been there, and, hopefully, are saying hello! from the other side.

There are a few reasons Beyoncé is performing “Crazy In Love” to this day. The first? It cemented the fact that the now global superstar could be a solo act. Upon its release in 2003, Beyoncé was still technically a member of Destiny’s Child but decided to put out a record all by herself. Obviously, it was a sweeping success with multiple lingering No. 1's on the Billboard Hot 100. The second? It empowers its audience to admit exactly how it feels to love *gulps* a man. Perhaps love is too benign a word. “Maintain an honest-to-goodness obsession for” is more like it.

Even if it’s been a while since someone’s got you sprung, “Crazy In Love” does what every good song should do: Summons the (hopefully not-so-distant) memory.

To hear The-Dream tell it, he wrote “Umbrella”—from start to finish—in about the time it took to sing the demo. So, in about four and a half minutes, one of the great pop standards of the 21st century was born. He told himself, “Write a hit!,” and so he did with the song that took Rihanna from star to superstar, lodging at the No. 1 spot on the Billboard Hot 100 for seven weeks. It was initially offered to Britney Spears and then Mary J. Blige, who must have subsequently kicked themselves (or their teams) for not jumping on it. It probably would have been a hit by any artist, but it does seem perfectly suited for Rihanna, who sings with a fierceness befitting devotion. Tricky Stewart’s chrome-coated drums, midtempo in their lumber, give the whole thing a majesty fit for a newly crowned pop queen.