With “Endless Summer Vacation” Miley Cyrus Turns a Skeptic Into an Admirer

Vincent Anthony
13 Min Read

“Endless Summer Vacation” is the first time I have ever cared to listen to a Miley Cyrus album in full. Growing up, I generally avoided her. 

My love for music began in the 90s via Mariah Carey, Janet Jackson, and Destiny’s Child. I considered myself wise beyond my years when it came to my music taste. Refined, if you will. Maybe I was elitist, but my faves are kind of legendary. They took innovative and introspective risks to create music that empowers and inspires listeners, opening doors for the current generation of pop stars.

Hannah Montana? No, thank you.

When Miley debuted as the star of the Disney Channel’s “Hannah Montana” series in 2006 I was 16 and too old to care about a kids’ show. Disney Channel pop stars were never my thing. 

Admittedly, I liked my fair share of Y2K Pop stars. For a time, I enjoyed Britney, *NSYNC, the Backstreet Boys, and the Spice Girls, but quickly deemed them “manufactured.” I moved on to singers who I considered to be “real” artists who were musicians, songwriters, vocalists, and visual innovators. They were in control of their careers and sound. Miley not only benefited from nepotism, but she was a Disney kid star, manufactured to be squeaky clean, cranking out bubblegum pop. She was literally a character. Young Miley didn’t stand a chance with me.

Miley’s bubblegum pop era peaked with the ubiquitous hit “Party in the U.S.A.” that I hated then, and still avoid now. I’d rather just play the Jay-Z song she never heard. Strike one. 

Good Girl Gone Bad? Please.

Of course, like all the other Disney kids, Miley quickly rebelled – changing her sound and image for post-Hannah Montana. It started with “Can’t Be Tamed” in 2010, which I found to be extremely annoying. Strike two.

It was with her first official album as an adult, “Bangerz,” that Miley took a more drastic turn: to hip-hop. This pivot to hip-hop seemed disingenuous at best, and textbook cultural appropriation at worst. I didn’t care enough to sort out the finer points. Twerking on Robin Thicke at the VMAs? Swinging naked on a ball and chain while belting a ballad? I didn’t understand who she was, or trying to be. I might be a white guy from the suburbs of Long Island, but I have a genuine appreciation for R&B, hip-hop, and the Black superstars who define those genres. I can tell the difference between appreciation and appropriation; it’s a fine line, and Miley crossed it. Like she said in 2009, she never heard a Jay-Z song, but released a hip-hop inspired album 4 years later? She had never really grabbed me, and here, she lost me. Strike three.

From Chaos to Calm

From there, Miley seemingly spiraled via increasingly chaotic choices, and I looked the other way. I’ve never been one to enjoy watching a wreck. There was an experimental psychedelic album released for free in 2015, a country-tinged pop album with cowgirl imagery in 2017, and a bunch of one-off singles through 2020.

It was 2018’s “Nothing Breaks Like a Heart,” a collaboration with Mark Ronson, that finally opened my ears to Miley. She sings it with a vocal delivery that is a bit country, yet almost soulful. It was pop for sure, but with disco and country vibes. The song was perfect for Miley, and damn good, too. In the video, she is sexy, mature, and confident. Both her talent and her identity were becoming a bit more refined. I was warming up to her.

So, when 2020’s “Midnight Sky” dropped to rave reviews, I gave it a listen and loved it. It’s a nostalgic bop that’s full of emotion, yet fun to sing along to. Still, I wasn’t intrigued enough to give the album, “Plastic Hearts,” a spin. The song almost leaned too hard into its inspirations. Rather than sounding like an 80s-inspired pop song, it sounded like a cover. It lacked innovation or progression; dare I say, as much as I love it, it is a bit… reductive.

In 2016, Miley said Mariah Carey had a “shtick.” In an interview with ELLE, she said, “It’s about Mimi! It’s about what she’s wearing, and it’s about her. What I make isn’t about me. It’s about sharing my story; it’s about someone being connected to what I’m saying.” 

Honestly, I can’t say this didn’t increase my indifference toward her. It was just so wrong. If anyone had a shtick, I thought, it’s Miley, not Mariah. Looking at Miley’s career in 2016 and prior, I struggled to see any clear story. There was no cohesion, just chaos. I couldn’t connect, in fact, I was wholeheartedly averse to the idea.

New Year, New Schtick

As 2022 came to a close, Miley teased the announcement of a new era with the phrase “New Year, New Miley,” using her perpetual identity crisis as a promotional tool. I saw this and thought, “Here she goes!” but this time, I laughed with her, not at her. 

Twelve days into the New Year, she dropped “Flowers,” a bittersweet, disco-pop bop that perfectly leverages Miley’s unique voice and empowering image. I was impressed and captivated by the song, and video. Everyone else was too, apparently: the song broke streaming records to debut at #1 on the Hot 100. Overall, it spent 8 weeks at the pole position. Miley is back, with her biggest hit – ever. Truthfully, it deserves. Finally, I gave in after over a decade of resistance: I wanted to hear this Miley Cyrus album.

Perhaps it is the perfect storm for both Miley and myself. I’m ten years older than I was when Miley released her first grown-up album, “Bangerz,” which put a bad taste in my mouth. Personally, I’ve matured since then, becoming a bit more open-minded to the pop girlies I had shunned for one reason or another, warranted (cultural appropriation) or not (my semi-elitist attitude). As for Miley, she’s done a lot of growing too.

Flowers in Bloom

Seven years later, that all has changed. I’ve always gravitated toward divas who make relatable, empowering content. Serious, personal, put you in your feels, and then lift you right back out anthems. That’s what Miley gave us with “Flowers,” and it is a great representation of the album as a whole. Lyrically, “Endless Summer Vacation” and its lead single delve heavily into her post-divorce emotional reckonings. She takes risks with introspective explorations of her feelings and liberating celebrations of her independence.

The album is solid throughout, with barely a skip to be found. It’s a cohesive body of work, yet each song has its own distinct vibe. Early in her career, Miley was chaotic, and here, she still is – but somehow, also chill. With this incarnation of Miley, her contradictions work.

Cohesive Contradictions

“Jaded” is unapologetically apologetic. She somehow manages to deliver it, vocally, with sass and sincerity. “Rose Colored Glasses” is sexy yet sad and is the source of the album title. “Endless summer vacation/ Make it last til we die,” she sings, attempting to live in a perpetual state of blissful ignorance, perhaps reflecting on trying to make things work with one of her recent exes. The album relishes in contradictions: both summer and vacations are temporary temporary things, but Miley labels them endless. 

I always like to look at the credits on a new album, and I was particularly surprised by those of “Thousand Miles,” which features Brandi Carlile. I figured the pair wrote the song together, but in fact, it was co-written by Miley, Tobias Jesso (Adele, Harry Styles), Bibi Bourelly (Rihanna, Mariah), and hip-hop producer and longtime collaborator of Miley’s, Mike Will. This song, and its credits, are a great representation of the album, and Miley. It’s an amalgamation of the wide range of inspirations, genres, and identities she’s explored throughout her career. Except, here, she’s finally gotten them all to work well together. It’s reminiscent of Beyoncé’s approach to crafting albums, the way she’s brought together unlikely collaborations and combinations. Miley has not only figured out what works for her, but how to make it slay

“Handstand” is perhaps the most unique song on the album, it opens with a spoken word poem that gives Lana Del Rey vibes, though her speaking voice recalls Lady Gaga. The closer to the “AM” section of the album, it’s like a palate cleanser with its slinky, atmospheric vibe. It’s sexy and catchy, but somehow unassuming. The contradictions continue, keeping things interesting.

As “Flowers” is the “AM” half’s opener, the album’s second single “River” opens its “PM” side. This energetic dance-pop track recalls the 80s sound and melody of Flo Rida and Kesha’s 2009 hit single “Right Round,” and even emulates its not-so-subtly sexual double entendre. Though Miley’s is not so blatant, like the assumed metaphor of Mariah Carey’s “Honey,” it’s there if you look for it. It may take a page from the Queen of Christmas, but it’s not a cover of the Joni Mitchell sometimes-Christmas standard, that’s for sure. Is she sure she’s never been a fan?

On standouts “Violet Chemistry” and “Muddy Feet,” Miley taps one of pop music’s most trustworthy hitmakers, Sia, to co-write and feature on the latter. “Violet Chemistry” boasts what’s become a rarity in pop music as of late: a bridge. When the beat flips and drops and Miley sings, “mixing up the colors like we’re making a Monet”?! Listen! Jay-Z once said, “Somewhere in America, Miley Cyrus is still twerking.” A decade later, here she is, inspiring gyration. 

Endless and Emblematic

While much of the album finds Miley in an emotional state, delivering strong, guttural vocals, on “Island” she achieves a similar but even more subdued version of chaotic cool, as found on lead single “Flowers.” The track is exactly what you’d expect from its title: a gorgeous, breezy tune that has a peaceful vibe of an island paradise. Perfect for an “endless summer vacation.”

With “Endless Summer Vacation,” a more mature Miley Cyrus indeed gave herself flowers — and they compose a bouquet of all the genres and eras of music she’s experimented with throughout her career. Together, these flowers are the centerpiece of her career. At 30, she’s finally found her musical identity, having delivered what is sure to become her defining album. Oh, and not that she cares, but she’s gained herself one more fan in the process.

Listen to “Endless Summer Vacation” by Miley Cyrus

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Vincent is the founder of the magazine and has had a strong passion for popular music since, well, 1997! If it's not obvious, his favorite artists include Destiny's Child, Mariah Carey, Janet Jackson, Michael Jackson, P!nk, and many more. Vincent lives in New York, where he is a high school English teacher, and currently he is pursuing a Master's in Journalism at the Craig Newmark Graduate School of Journalism at CUNY.