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Miley Cyrus' Road To 'Endless Summer Vacation': How Hannah Montana, Artistic Reinvention & Heartbreak Led To Her Most Self-Assured Album Yet
As Miley Cyrus releases her eighth studio album, she's riding high on her biggest hit to date with "Flowers" — and it's all a culmination of an experimental creative and personal journey that's helped her become the truest version of herself.
In the frigid depths of January, Miley Cyrus pronounced an Endless Summer Vacation was on its way. But it wasn't just the promise of perennial sunshine and lazy days by the pool in the near future — it was the title of her eighth studio album.
Cyrus has always been a musical shapeshifter, dating all the way back to her days as a Disney star. In fact, to call her a chameleon is something of an understatement. More than any of her contemporaries in the Disney Channel class of the late 2000s, the superstar has zigzagged wildly from genre to genre, and aesthetic to aesthetic, across more than 15 years in the business.
Of course, before Cyrus became a pop star in her own right, she was known to an entire generation as Hannah Montana, the titular character of the hit Disney Channel sitcom that ran from 2006 to 2011. Portraying Hannah gave the then-child star her first taste of life as a (fictional) music sensation, one who lived in the "Best of Both Worlds" and could put her fame on like a costume by adopting a stage persona and new look.
When looking at Cyrus' wide-spanning career, it could be argued that the foundational experience of playing Hannah Montana informed the way a young Miley approached her own identity as a pop star, shifting from one style to the next — and yet, having each of them feel entirely authentic to her talent and point of view.
Despite the sometimes drastic stylistic changes from one album to the next, Cyrus has always insisted her music is rooted in personal truth and reflective of her current moment. "Everyone that I've been — whether you are thinking about Hannah Montana or the music I made in the past — all of it has always been the truth," she said in a 2017 interview with NPR. "So I think people are saying 'the new Miley' or 'the more honest Miley' — I've always been that. But I've been honest for who that person was then."
The singer first started breaking away from her Hannah Montana character long before the kid-friendly series finished airing in 2011. Establishing her own identity happened in fits and starts, even as her persona as Hannah grew larger than life. In 2007, she released Hannah Montana 2: Meet Miley Cyrus — a part soundtrack/part double album to introduce fans to the budding artist underneath Hannah's blonde wig. The project earned Cyrus her very first top 10 hit in the form of "See You Again."
In the years that followed, she essentially lived parallel lives as both Miley and Hannah. Breakout, her second studio album, arrived in 2008 with singles "7 Things" and "Fly on the Wall," and yet Hannah was still making appearances on her Best Of Both Worlds Tour. "I think having Hannah come up on stage gives it a cool vibe," she explained to MTV News at the time. "And it shows, like, one girl but definitely two sides and I like that you get both tastes of music, and I think it's just really fun."
That dichotomy continued the following year when her alter ego made the leap to to the big screen in Hannah Montana: The Movie. And yet, Hannah's big break also gave Miley the perfect platform to debut "The Climb," the soundtrack offering that rose all the way to No. 4 on the Billboard Hot 100 and became her highest-charting single at the time.
As with many child stars before her, the time eventually came for Cyrus to grow up, and as she pushed against the constraints of her kid-friendly image, controversy came calling. First, there was the pearl-clutching over "Party in the U.S.A.," with Miley's short shorts and playful pole dancing at the 2009 Teen Choice Awards; nearly a year later, her cheekily titled third album, 2010's Can't Be Tamed, sparked minor outrage over the themes and title, as well as the slight raciness of the title track's music video.
However, if the road to autonomy started out a tad bit bumpy, Cyrus burned the bridge to her tween idol past to cinders with her fourth album, 2013's Bangerz.
As its brash title suggests, the studio set is indeed a collection of banger after banger — and a provocative swerve into party-ready hip-hop and electro-pop, including a tracklist filled with all-star guest features like Britney Spears (the fan favorite "SMS (Bangerz)"), Nelly (the country-fried stomp of "4x4"), Big Sean (the blurred-out "Love Money Party"), Future (Ben E. King-sampling highlight "My Darlin'") and more. And stylistically, Miley had traded in both her long brunette waves and Hannah's signature blonde wig for a platinum pixie cut, bold red lip and rotating wardrobe of barely-there bodysuits made from latex and the pelts of abandoned teddy bears.
In retrospect, the album is unequivocally part of the defining soundtrack to the early 2010s. While the most indelible image from the Bangerz era was Miley swinging naked and free atop a giant wrecking ball, lead single "We Can't Stop" became the hedonistic anthem for a then-rising generation of young millennials coming of age in the post-recession years of Obama's second term — Cyrus included.
And for as much scandal as Miley gleefully courted during the era — whether over her appropriation of hip-hop and Black culture, that unforgettable VMAs performance with Robin Thicke, all the twerking, or the constantly stuck-out tongue of it all — the album also earned the singer her first, and so far lone, solo GRAMMY nomination for Best Pop Vocal Album. Still, even Miley can admit all these years later that she'll pretty much "never live down that I licked a sledgehammer."
Following a project like Bangerz, most pop stars might perform something of a label exec-encouraged course correction into less provocative territory. But Miley isn't just any pop star. So, instead, she took her antics, and her music, even further down the rabbit hole with Miley Cyrus & Her Dead Petz in 2015.
Enlisting a trusted pair of Bangerz producers, Mike WiLL Made-It and Oren Yoel, the singer added a psychedelic bent to her existing oeuvre by teaming with Wayne Coyne and the rest of the Flaming Lips. The resulting project — which opened with the discordant declaration, "Yeah I smoke pot, yeah I love peace/ But I don't give a f—, I ain't no hippie!" — was so experimental and decidedly noncommercial that it was originally released independently, available to stream for free on Soundcloud. (While it didn't count towards her multi-album deal with RCA, the album was later added to traditional streaming services by the label, but never made a mark on the Billboard 200 or any other official chart.)
"I created my surroundings, my own world. What seems like fantasy or trippy, it's not to me. It's my actual reality," the star explained in a profile in the New York Times about the oddball release, and argued that despite its lack of traditional, well, bangers, it was actually an innate progression from its pop-heavy predecessor.
"When I made Bangerz, it was as true to me then as this record is now," she told the NYT. "It just happened naturally in my head. It's like anything — styles just change…I literally can do whatever I want. It's insane. This music was not meant to be a rebellion. It was meant to be a gift."
For his part, Miley's trusty right-hand man Mike WiLL Made-It saw her evolution through much the same lens, declaring to the NYT, "Why would she drop another Bangerz? Miley is the new Madonna."
Of course, there's only so far off the yellow brick road you can go before risking losing your fanbase to woozy fields of poppies. No matter how delayed, the course correction was bound to come — "what goes up must come down," as the saying goes and all that — but like every other step of her evolution, Miley veered back to the middle of the road entirely on her own terms.
Not only was Younger Now, her fifth album from 2017, a sonic shift to rootsy country pop (led by the downtempo, dreamy "Malibu"), it was also the first time Cyrus laid bare her approach to personal and artistic reinvention in song. "Feels like I just woke up/ Like all this time I've been asleep/ Even though it's not who I am/ I'm not afraid of who I used to be," she intoned on the opening title track, decked out in her best rockabilly cosplay before preaching, "No one stays the same/ Know what goes up must come down/ Change is a thing you can count on/ I feel so much younger now."
The album cycle was also marked by seismic changes in Cyrus' personal life. In 2016, she reconciled with longtime on-and-off boyfriend Liam Hemsworth and by the time Younger Now was released into the world, the pair were engaged to be married. The romance had gone through many different stages, breakups and reconciliations since the duo met filming The Last Song in 2009, but Cyrus had no idea at the time just how impactful it would turn out to be in the years to come.
At the time she dropped Younger Now, the superstar actually confessed her enthusiasm had already waned for her singer/songwriter phase — one natural drawback to her need for constant creative reinvention. "I'm over this now," she said during a promotional visit from BBC Radio 1 at her home studio in Malibu two full weeks before the album debuted at a career low of No. 5 on the Billboard 200. "I want to figure out what I want to do next."
If her 2019 EP She Is Coming is any indication, what Miley originally had planned was a full-circle return to her role as pop provocateur. The seven-track sampling came across as a sort of Bangerz 2.0, trading the debauchery of "We Can't Stop" for the unabashed political message of lead single "Mother's Daughter."
The EP was meant to be the first in a trilogy that would eventually make up a full-length record, but the idea was scrapped when another metaphorical wrecking ball came crashing through the pop star's life: In August of that year, she announced her separation from Hemsworth after just eight months of marriage. Two weeks later, the actor officially filed for divorce. But even before he'd filed the papers, Cyrus had released standalone single "Slide Away" to eloquently and powerfully tell her side of the story.
"Once upon a time it was paradise/ Once upon a time I was paralyzed/ Think I'm gonna miss these harbor lights/ But it's time to let it go," she reflected, cutting her losses before bluntly telling her ex, "Move on, we're not 17/ I'm not who I used to be/ You say that everything's changed/ You're right, we're grown now."
Although it had spanned more than a decade of her life, Miley had never been so autobiographical about her relationship in her music up to that point — and the emotional vulnerability seemed to crack open a door she still has yet to close.
In fact, it's easy to see the throughline connecting "Slide Away" to cuts like "Midnight Sky," "WTF Do I Know" and "Never Be Me" off her excellent 80s-inspired seventh album Plastic Hearts, even through the glam rock sheen and covers of Blondie, Metallica and the Cranberries.
By the time Plastic Hearts was ready to be unwrapped in late 2020, Miley had also made peace with all the versions of herself that had come before. "I discredited myself for what I had been almost every step of the way," she said in a Rolling Stone cover story. "During Dead Petz, discrediting Bangerz. During Bangerz, discrediting Hannah Montana. During "Malibu," discrediting Bangerz. It's almost like when I have evolved, I've then become shameful of who I was before. What makes you an adult, I think, is being OK with who you've been before."
That personal reckoning is part of what makes "Flowers," the lead single off Endless Summer Vacation, feel like such a victorious culmination of what makes Miley Cyrus a superstar. The disco-inspired track is a testament of self-determination and hard-won independence, and has already become the biggest hit of her career by a long mile before the rest of the album even drops. She's broken colossal streaming records set by the likes of Adele not just once but twice over and spent six consecutive weeks at No. 1 on charts across the globe.
The rest of Endless Summer Vacation is divided into two sides — A.M. and P.M. — representing different acts of a complete story. But even before fans heard the new album, it was clear Cyrus had already arrived at the most fully-formed version of herself yet.
"I hope this show is a representation of you never need[ing] to choose who you want to be. And you don't need to fit into any boundaries or into any boxes," she told the rapt crowd at the 2022 Super Bowl Music Fest, which was recorded for her live album ATTENTION: MILEY LIVE ahead of Endless Summer Vacation's arrival. "You can be anything and everything that you've ever wanted to be all at the same time."
The singer knows that better than just about anyone. After all, she's just being Miley.

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New Music Friday: Listen To New Releases From Miley Cyrus, Selena Gomez, Blackpink & More
The summer of 2023 may be winding down, but its musical offerings remain white-hot. Check out some new songs and albums that arrived on Aug. 25, from Maluma to Burna Boy.
The faintest hint of fall is in the air, but the summer of 2023's musical deluge continues unabated. Across genres, scenes and styles, the landscape continues to flourish.
We have Miley Cyrus's first song since Endless Summer Vacation — a vulnerable, proudly "unfinished" offering. On the opposite end of the vibe spectrum, Selena Gomez has thrown caution to the wind with the carefree "Single Soon."
And that's just the beginning — beloved acts from Burna Boy to BLACKPINK are back with fresh material. Before you dive into the weekend, add these songs to your playlist.
Miley Cyrus — "Used To Be Young"
On her first song since Endless Summer Vacation arrived in March, two-time GRAMMY nominee Cyrus avoids tidiness, and pursues honest reflection.
"The time has arrived to release a song that I could perfect forever. Although my work is done, this song will continue to write itself everyday," she said in a statement. "The fact it remains unfinished is a part of its beauty. That is my life at this moment ….. unfinished yet complete."
"Used to Be Young" belongs to the pantheon of "turning 30" jams; therein, Cyrus looks back on her misspent youth, and the attendant heat of the spotlight. "You say I used to be wild/ I say I used to be young," she sings.
In the stark video, she gazes unflinchingly into the lens, without varnish or artifice.
Selena Gomez — "Single Soon"
Where Cyrus' new song bittersweetly gazes backward, Gomez's carbonated new jam "Single Soon" is focused on the promised reverie of tomorrow — sans boyfriend.
"Should I do it on the phone?/ Should I leave a little note/ In the pocket of his coat?" the two-time GRAMMY nominee wonders, sounding positively giddy about her unshackling from Mr. Wrong.
As the song unspools, Gomez gets ready for a wild night out; the song ends with the portentous question, "Well, who's next?" If you're ready to slough off your summer fling, "Single Soon" is for you.
Ariana Grande — Yours Truly: Tenth Anniversary
The two-time GRAMMY winner and 15-time nominee's acclaimed debut album, Yours Truly, arrived on Aug. 30, 2013; thus, it's time to ring in its tin anniversary.
Granted, these aren't "new songs," per se: rather, in a weeklong celebration, Grande is reintroducing audiences to Yours Truly.
Dive in, and you'll find "Live From London" versions of multiple songs. Plus — perhaps most enticingly — the sprawling re-release contains two new versions of "The Way," her hit collaboration with late ex Mac Miller.
Maluma — Don Juan
Papi Juancho is dead; long live Don Juan. "Fue un placer," Maluma wrote on Instagram last New Year's Eve. (It translates to "It was a pleasure.")
And with that, the Colombian rap-singing heavyweight ushered in a new character. He's now Don Juan — in a reference both to the fictional libertine and his birth name of Juan Luis Londoño Arias.
Now, Don Juan's out with his titular album — which he dubs a "mature" blending of the musics that got him going, like reggaeton, house, salsa, and hip-hop.
Burna Boy & Dave — "Cheat On Me"
Just over a year after his latest album, Love, Damini, Burna Boy is back with I Told Them… The Nigerian star offers another forward-thinking missive with his seventh album.
Featuring the likes of 21 Savage, J. Cole, and Wu-Tang Clan's GZA and RZA, I Told Them… is one highlight after the next — and "Cheat On Me" is one of them. For the advance single, the GRAMMY-winning Afro-fusion dynamo teamed up with London rapper Dave.
Therein, the pair expound on getting out of their own way. The chorus, powered by a sample from British-Ghanian singer/songwriter Kwabs, sums it all up: "I couldn't see/ I was cheating on, cheating on me."
Blackpink — "The Girls"
BLACKPINK are a bona fide cross-cultural sensation, but they won't stop at the music: they're a game now.
A little over a year after their second studio album, Born Pink, the acclaimed South Korean girl group has released a mobile app, succinctly called "The Game." Therein — and above — players can watch the video for "The Girls," their first post-Born Pink jam.
Don't say Jisoo, Jennie, Rosé, and Lisa didn't warn you: "Stop sign, we're burning it down/ Better watch out, we coming in loud/ Bang, bang, just playing around/ Don't mess with the girls, with the girls, with the girls."
The Killers — "Your Side of Town"
The Killers' beloved debut album, Hot Fuss, turns 20 next year; as a ramp-up, here's "Your Side of Town," a new slice of electro-pop from the Vegas crew.
The sleek, aerodynamic, Auto-Tuned "Your Side of Town" is their first single since their acclaimed pair of albums, 2020's Imploding the Mirage and 2021's Pressure Machine.
Here, the five-time GRAMMY nominees take a Pet Shop Boys-like tack with the music; lyrically, they're still putting the "heart" in heartland rock.
"I'm hanging on your side of town/ I notice when you're not around," frontman Brandon Flowers sings on the chorus. "Can't keep my cool, I'm burning inside/ A broken heartbeat, barely alive."
But the Killers — like everyone on this list — remain very alive.
New Music Friday: Listen To New Songs From Travis Scott, Britney Spears, NewJeans & More

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9 Songs You Didn't Know Jon Bellion Wrote & Produced: Hits By Justin Bieber, Selena Gomez & More
Pop superproducer Jon Bellion is the man behind Tori Kelly's new ep, 'tori,' but he's also been involved with countless hits for more than a decade. Check out nine of Bellion's biggest songs, from Eminem to Jonas Brothers.
If the name Jon Bellion sounds familiar, it's probably because of his 2016 single "All Time Low." With its relentless "low-low-low-low-low" chorus, the electronic-fused pop confection scored Bellion his first major hit — as a solo artist, that is.
Prior to Bellion's breakthrough with his debut solo single, he'd already made a name for himself behind the scenes by writing and producing songs for the likes of Eminem, Jason Derulo, Zedd and CeeLo Green. And in the seven years since "All Time Low" became a top 20 hit, he's celebrated plenty of other smashes with some of pop's A-listers from Christina Aguilera to Justin Bieber.
This year alone, he worked with the Jonas Brothers to executive produce their statement-making record The Album, helped shape Maroon 5's "Middle Ground" — which is expected to be the lead single off the veteran pop-rockers' forthcoming eighth studio album — and teamed up with Switchfoot for an orchestral 2023 update of the band's 2003 breakout single "Meant to Live."
Bellion's most recent work can be heard on Tori Kelly's new self-titled EP tori, which dropped July 28. Along with producing the project, Bellion joined Kelly for a magnetic, electro-tinged track titled "young gun." Upon the EP's release, Kelly herself noted Bellion's impact, calling their collaboration "the start of something really special."
In honor of Bellion's latest project, take a look at nine songs you may not have known contained Bellion's signature touch — a roadmap to his becoming one of the most in-demand producers of the moment.
Eminem feat. Rihanna — "The Monster"
One of Bellion's earliest smashes came courtesy of Eminem — well, and Bebe Rexha. The pop singer penned the track's dark hook while working on her debut album, but it later made its way to Eminem and eventually shapeshifted into his fourth collaboration with Rihanna. The song became the duo's second No. 1 collaboration following 2010's "Love The Way You Lie" and remains one of most monstrous hits in Bellion's career.
Jason Derulo — "Trumpets"
Jason Derulo worked solely with Bellion on this top 20 hit from his 2013 Tattoos, which was later re-packaged as 2014's Talk Dirty. Built around an irresistible horn line of, yes, literal trumpets, Bellion and Derulo concocted a bouncy, flirtatious symphony to smoothly objectify the R&B singer's lady love, and manages to name drop Coldplay, Katy Perry and Kanye West over the course of just three minutes and thirty-seven seconds.
Christina Aguilera feat. Demi Lovato — "Fall in Line"
Bellion handled production on Christina Aguilera's fierce 2018 team-up with Demi Lovato, "Fall in Line," off the former's 2018 LP Liberation. Behind the boards, Bellion effectively captured all of the feminist rage and empowerment that the two vocal powerhouses lit into their lyrics, pairing their sneering vocals with a vamping strings section, rattling chains and a robotic male overlord futilely demanding, "March, two, three, right, two, three/ Shut your mouth, stick your ass out for me."
"Fall in Line" scored a nomination for Best Pop Duo/Group Performance at the 2019 GRAMMYs, marking Aguilera's twentieth career nod and Lovato's second.
Maroon 5 — "Memories"
To kick off their seventh album, JORDI, Maroon 5 enlisted Bellion to co-write lead single "Memories." The gentle ballad found frontman Adam Levine mourning the loss of a friend, pouring one out over a lilting reggae-pop line that cleverly samples Johann Pachelbel's "Canon in D Major." While the heartfelt song is dedicated to the band's longtime manager (and namesake of the LP) Jordan Feldstein, who tragically passed away in 2017 due to a blood clot, the relatable sentiment of "Memories" helped it peak at No. 2 on the Hot 100.
In addition to "Memories," Bellion also worked with the band on two other songs from JORDI, co-writing fourth single "Lost" as well as Anuel AA and Tainy collab "Button." Three years later, he would reunite with the band to co-write and co-produce their latest, equally delicate single "Middle Ground" alongside the likes of Andrew Watt and Rodney Jerkins.
Miley Cyrus — "Midnight Sky"
Miley Cyrus came raring into her glam rock-inspired album Plastic Hearts on the back of "Midnight Sky," an unapologetic statement of independence following her split from longtime love Liam Hemsworth. Dripping in sultry synths, the power ballad took a page from '80s rock icons like Joan Jett, Debbie Harry and Stevie Nicks.
The sound was an entirely new one for Cyrus — which is one of Bellion's tools when working with a new superstar for the first time. In a 2023 Billboard interview, he likened his approach to inventing a new kind of ride for the given A-lister. "They have already built an amazing theme park: millions of people go to it and experience their roller coasters," he said. "They put me in charge of revamping or creating a new section of the theme park, and they let me be the foreman of it all." The new style worked in Cyrus' favor, and earned Bellion yet another top 20 hit on the Hot 100.
Justin Bieber — "Holy"
Bellion's fingerprints are all over Justin Bieber's 2021 album Justice, starting notably with its Chance the Rapper-assisted lead single "Holy," which he both co-wrote and co-produced. The superproducer contributed to six other songs on the pop-driven LP — including the pop radio No. 1 "Ghost," which was inspired by Bellion's late grandmother — as well as three deluxe tracks. And though Bellion didn't have any credited features, his voice can still be heard: he offered background vocals on seven of the songs.
Justice earned Bellion his very first GRAMMY nomination, as the project was nominated for Album Of The Year at the 2022 GRAMMYs (Bieber also received seven other nods).
Selena Gomez — "My Mind & Me"
Bellion first collaborated with Selena Gomez on Rare album cut "Vulnerable" alongside Amy Allen, Michael Pollack and The Monsters & Strangerz. Two years later, the entire team reunited for the title track to the pop singer's Apple TV+ documentary My Mind & Me.
Bellion and co. helped Gomez tap even further into the most vulnerable side of her psyche to date. "Vulnerable" saw Gomez letting her guard down with a new flame, but "My Mind & Me" allowed her to completely lay bare her mental health journey. "Sometimes I feel like an accident, people look when they're passin' it/ Never check on the passenger, they just want the free show," she sings. "Yeah, I'm constantly tryna fight somethin' that my eyes can't see," over spare guitar and piano.
Jonas Brothers — "Waffle House"
After the success of their 2019 comeback album Happiness Begins with producer Ryan Tedder, the Jonas Brothers recruited Bellion to helm the boards on their 2023 follow-up The Album. The producer helped the hitmaking siblings tap into a new facet of their pop-rock sound, finding inspiration in the '70s music their dad raised them on. (As Joe Jonas told GRAMMY.com upon the album's release, Bellion "was saying exactly what we were hoping for" when they first met to mull over ideas.)
While Bellion had a hand in every song on The Album, second single "Waffle House" is the latest to earn both him and Jonas Brothers a top 15 hit on pop radio. Bellion also serves as the one and only featured artist on The Album, coming out from behind the boards and into the vocal booth for bombastic closer "Walls."
Tori Kelly — "missin u"
Tori Kelly first linked up with Bellion thanks to Justin Bieber, as the pair worked together with the Biebs on tender bonus cut "Name" from the Justice sessions. So, when it came time to launch a new era with her self-titled EP tori, the songstress turned to Bellion to help bring her vision to life.
On lead single "missin u," the two-time GRAMMY winner throws the guitar-driven singer/songwriter vibes of her past work out the window in favor of a sleek R&B sound reminiscent of the early 2000s. The sonic gear shift is a natural fit for her lithe voice as she replays a romance that "was rainin' purple skies in my room." Somehow, Kelly even manages to outdo the vocal acrobatics of "missin u" with a deliriously brilliant "R&B edit" that adds even more layers, soul and vocal flourishes to the single.
"When I first started working with Jon Bellion, we were just beginning to scratch the surface on a new sound that truly felt like my own," Kelly explains in a video celebrating the release of her self-titled EP tori. "I know that I'm gonna look back on this collaboration as the start of something really special." As for Bellion's thoughts on his latest project? "Tori Kelly's the greatest vocalist of all time!"
Ariana Grande's Musical Growth In 15 Tracks, From "The Way" To "Positions"

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Loving Olivia Rodrigo's "Vampire?" Check Out 15 Songs By Alanis Morissette, Miley Cyrus & More That Reclaim The Breakup Narrative
From the soft hums of Carole King's "It's Too Late" to GAYLE's fiery rage on "abcdefu," these 15 songs encapsulate the expansive emotions of women who put problematic exes in their place — far behind them.
Since the 2021 release of SOUR, critics and listeners alike have touted Olivia Rodrigo for her knack to eloquently pen the relatable woes of adolescence and the pitfalls of falling in love too hard. Her latest single, "vampire," is no different.
Despite trading in her "drivers license" teenage loverboy for an older man, the perfectly executed expression of agony remains. As Rodrigo wails on the chorus, "You made me look so naïve/ The way you sold me for parts/ As you suck your teeth into me/ Bloodsucker, famef—er/ Bleeding me dry like a g——n vampire."
But before there was Rodrigo, there was Avril Lavigne, Taylor Swift, and Alanis Morissette — none of which would be where they were without pioneers of diaristic songwriting, Carole King and Carly Simon. Thanks to the immortalization of their music, we can relive the shift from poetic disclosures of hurt, which King exemplifies on "It's Too Late," to more unrepentant, straightforward jabs (like Kate Nash says on "Foundations," "Don't want to look at your face 'cause it's making me sick") and harrowing battle cries (as Miley Cyrus roars, "I came in like a wrecking ball").
Below, revisit 15 songs by empowered women, from 1971 all the way to 2021, who reclaimed the breakup narrative with their fervent sentences of damnation — because, as the age-old saying goes, hell hath no fury like a woman scorned.
Carole King — "It's Too Late" (1971)
When Carole King released "It's Too Late" in 1971, it marked a new era of songwriting. Discussions about divorce were generally unheard of, but even more so when initiated by a woman. Yet, King carried on to unapologetically release "It's Too Late," which later won a GRAMMY for Record of the Year and is lauded by Rolling Stone as one of the 500 Greatest Songs of All Time.
On this folky track, King and her husband's inevitable parting is on the horizon, but she isn't resentful per se. Instead, she's more troubled by the embarrassment of her husband's growing discontent, admitting, "I feel like a fool." And at this point, she's ready to move on and can be grateful for the times they've shared.
Carly Simon — "You're So Vain" (1972)
In her '70s chart-topper, Carly Simon narrates the tale of an arrogant man who believes every woman is enchanted by his aura. But the folk songstress wants to make it very clear she's not impressed by his embellished stories or luxurious closet.
Usually, it's easy to guess the subject of a breakup song, but "You're So Vain" has led to decades of speculation. Many have assumed it could be about James Taylor, who Simon married in 1972 and divorced in 1983, or Mick Jagger, who provided vocals to the track (a theory that was later debunked). To this day, she has only revealed the track's inspiration to a select few, including Taylor Swift, who names Simon as one of her role models.
Joan Jett And The Blackhearts — "I Hate Myself For Loving You" (1986)
Joan Jett might not give a damn about her bad reputation, but she despises nothing more than her ex-lover making her look like a lovesick fool.
On "I Hate Myself for Loving You," the '80s chanteuse wraps herself around a classic glam rock beat, unveiling her contempt for a man who's neglected her. Stripped of her pride, Jett begins to resent herself for holding onto her feelings — as evidenced by the song's title.
She tries to hide her dwelling desires ("I want to walk, but I run back to you") but ultimately fails to rid herself of the emotions, leaving her to fantasize about the sweet justice of one day roping him back in, just to leave him.
Alanis Morissette — "You Oughta Know" (1995)
It's impossible to talk about scathing breakup songs without acknowledging Alanis Morissette's quintessential heartbreak anthem, "You Oughta Know." At the time of its release, the Jagged Little Pill single contained some of the most honest and vitriolic lyrics in existence.
Morissette begins with an illusive statement, "I want you to know that I'm happy for you," which, by the second verse, crumbles into a revelation, "I'm not quite as well, you should know." As she culminates into her most confessional, the instrumental rises into an addicting ruckus, with Morissette revealing the thoughts most of us would be too ashamed to admit: "It was a slap in the face how quickly I was replaced/ And are you thinkin' of me when you f— her?"
Shania Twain — "That Don't Impress Me Much" (1997)
Shania Twain has a particular superpower of delivering each of her lyrics with an air of lightheartedness and confidence. So, when you hear a track like "That Don't Impress Me Much," her disappointment and irritation becomes undetectable.
A quick examination of Twain's story proves — despite the song's bouncy melodies — she's jaded by her ex's preoccupation with his vehicle, appearance and intelligence. Sure, he might be perfect on paper, but he lacks the qualities of a forever lover, and his unmerited ego should be reserved for true big shots like Elvis Presley and Brad Pitt.
Michelle Branch — "Are You Happy Now?" (2003)
In the opening verse of "Are You Happy Now?," Michelle Branch pleads, "No, don't just walk away/ Pretending everything's okay, and you don't care about me." At first, she is in disbelief that her once admirer would swiftly brush her off, but as she reaches the chorus, she begins to question whether his actions were a lie all along.
Her mind racing, Branch teeters between shameless questions of "Do you really have everything you want?" and "Could you look me in the eye and tell me you're happy now?" But by the song's end, she gets the most satisfying payback of all — peace without him: "I'm not about to break/ 'Cause I'm happy now."
Avril Lavigne — "My Happy Ending" (2004)
"My Happy Ending" finds 2000s pop-punk maven Avril Lavigne grasping onto the shards of a broken relationship and trying to pinpoint where everything went wrong. She could have said the "wrong" thing, or her partner's misfit friends might have spoken negatively about her. But there is one thing she does know with certainty: there is no way to pick up the pieces.
Coming to terms with the truth, Lavigne repositions her anger toward the other person for stripping her of her fairytale ending, sarcastically acknowledging him for their time spent together over a somber piano: "It's nice to know you were there/ Thanks for acting like you care/ And making me feel like I was the only one."
Kelly Clarkson — "Gone" (2004)
Kelly Clarkson has traversed almost every emotion in love, from her epic breakup anthems like "Behind These Hazel Eyes" to her most recent LP chemistry. But "Gone" may just be her most unrelenting to date.
Introduced by its Breakaway counterpart "Since U Been Gone," the mononymous "Gone" extends Clarkson's journey of healing — this time, with a more explicit and mature diatribe against her ex's character. Rather than using trivial attacks, Clarkson instead chooses to call out his assumption she'd run back into his arms, later declaring an end to her toleration: "There is nothing you can say/ Sorry doesn't cut it, babe/ Take the hit and walk away, 'cause I'm gone."
Lily Allen — "Smile" (2006)
With "Smile," Lily Allen gets her sweet revenge through the sight of her former flame's tears and misfortune. But the lyrics of Allen's breakthrough single doesn't exactly clarify the specifications of her antics, only an explanation for its origins.
After a cheating scandal ends her relationship, her mental health plummets — until he comes crawling back for her mercy. Upon hearing his pleas, she comes to a realization: "When I see you cry, it makes me smile." And as the conniving music video shows, anyone who cheats on her will get their karma — perhaps in the form of organized burglary, beatings, and a laxative slipped into their morning coffee.
Kate Nash — "Foundations" (2007)
Following in the footsteps of her mentor Lily Allen, Kate Nash vividly paints the tragedy of falling out of love, made prismatic by her plain-spoken lyrics ("Your face is pasty 'cause you've gone and got so wasted, what a surprise!") and her charming, thick London accent.
In this story, Nash has not quite removed herself from the shackles of her failing relationship. In fact, she'd like to salvage it, despite her boyfriend's tendency to humiliate her and her irresistible urge to sneer back with a sarcastic comment. By the end of the track, Nash, becoming more restless, packs on new ways to inconvenience him — but in the end, still wonders if there's any saving grace to preserve their once blazing spark out of a fear of loneliness.
P!nk — "So What" (2008)
The year P!nk wrote "So What," she already had a bevy of platinum singles under her belt. With a gleaming social status and peaking career, she was apathetic to the temporary separation from her now husband, Carey Hart. Feeling the highs of newfound singlehood, P!nk was ready to incite personal tyranny, whether that meant not paying Hart's rent, drinking her money, or starting a fight.
Ironically, Hart appears as the antagonist in the music video, which P!nk revealed via her official fan website was a testament of their growth: "Carey hadn't heard the song before he did the video. That's how much he trusts and loves me [...] He gets it. He gets me," she said.
Taylor Swift — "Picture To Burn" (2006)
Taylor Swift has long solidified herself as the reigning queen of love songs, from ballads honoring the most committed relationships to diss tracks of heartbreaking adolescent flings. The latter houses one of the earliest (and most twangy) hits in Swift's sweeping catalog: "Picture to Burn."
In this deceivingly upbeat tune, Swift vows to seek vengeance on a boyfriend after he leaves her to date one of her friends — from getting with his friends to having her father give him a piece of his mind. And along the way, she will gladly dish out a few insults: "You're a redneck heartbreak who's really bad at lying/ So watch me strike a match on all my wasted time/ As far as I'm concerned, you're just another picture to burn."
Miley Cyrus — "Wrecking Ball" (2013)
Closing the door on her Hannah Montana days, Miley Cyrus' "Wrecking Ball" saw the childhood pop star in her most grown-up and vulnerable state to date. Months before the release, Cyrus had called off her engagement to her longtime boyfriend, Liam Hemsworth, paving the way for her thunderous performance on the Bangerz single.
Just as affecting as Cyrus' belting vocals is the track's iconic music video. Cyrus climaxes with a deafening cry — "All you did was wreck me" — as she swings across the screen on an actual wrecking ball, breaking down all her physical and metaphorical walls.
Halsey — "You should be sad" (2020)
By the mid-2010s, the industry had put angst on the back burner in exchange for feel-good EDM and trap beats. Well, that is, at least, until Halsey entered the picture.
After just two years in the limelight, Halsey had cultivated a vibrant assortment of sonic melodrama — from the dirt and grime of toxic, failed love on tracks "Bad at Love" and "Colors" to the Bonnie and Clyde-esque heated passion of "Him & I."
In 2020, Halsey rounded out her discography with the genre-bending, introspective Manic, where a track like "You should be sad" commands your attention with matter-of-fact, vindictive comments: "I'm so glad I never ever had a baby with you/ 'Cause you can't love nothing unless there's something in it for you."
GAYLE — "abcdefu" (2021)
Unlike most love songs, GAYLE refuses to point her fury on "abcdefu" solely toward her heartbreaker. The then-16-year-old singer, instead, rages against his mother, sister and pretty much anyone (and anything) he's associated with — other than his dog — across a searing melody with a bewitching bassline.
Earlier this year, GAYLE revealed to GRAMMY.com that she was "angry at him and was angry at the people who enabled him and his behavior." That animosity was palpable in "abcdefu," creating a magic as empowering as it is cathartic — and, like many songs that came before it, proving that there can be power in pain.

Photo: Kristy Sparow/Getty Images, Kevin Winter/Getty Images for LARAS, Kevin Winter/Getty Images for The Recording Academy, Alberto E. Rodriguez/Getty Images for The Recording Academy, Stephen J. Cohen/Getty Images, Gustavo Garcia Villa
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Listen To GRAMMY.com's LGBTQIA+ Pride Month 2023 Playlist Featuring Demi Lovato, Sam Smith, Kim Petras, Frank Ocean, Omar Apollo & More
Celebrate LGBTQIA+ Pride Month 2023 with a 50-song playlist that spans genres and generations, honoring trailblazing artists and allies including George Michael, Miley Cyrus, Orville Peck, Lady Gaga and Ariana Grande and many more.
In the past year, artists in the LGBTQIA+ community have continued to create change and make history — specifically, GRAMMY history. Last November, Liniker became the first trans artist to win a Latin GRAMMY Award when she took home Best MPB Album for Indigo Borboleta Anil; three months later, Sam Smith and Kim Petras became the first nonbinary and trans artists, respectively, to win the GRAMMY Award for Best Pop Duo/Group Performance for their sinful collab "Unholy."
Just those two feats alone prove that the LGBTQIA+ community is making more and more of an impact every year. So this Pride Month, GRAMMY.com celebrates those strides with a playlist of hits and timeless classics that are driving conversations around equality and fairness for the LGBTQIA+ community.
Below, take a listen to 50 songs by artists across the LGBTQIA+ spectrum — including "Unholy" and Liniker's "Baby 95" — on Amazon Music, Spotify, Apple Music, and Pandora.