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Olivia Rodrigo’s new album defies expectations, including her audience’s

Six years ago, while still legally a child, Olivia Rodrigo left her career as a Disney Channel actress with the intent of becoming a pop star. This is a tale as old as time, or at least as venerable as Annette Funicello’s singing career, and the blueprint for success is well understood: sign with a […]

Six years ago, while still legally a child, Olivia Rodrigo left her career as a Disney Channel actress with the intent of becoming a pop star. This is a tale as old as time, or at least as venerable as Annette Funicello’s singing career, and the blueprint for success is well understood: sign with a first-rate production team, let them handle pretty much everything but the TikTok videos, while you tour and promote past the point of exhaustion. Britney Spears, Miley Cyrus, Sabrina Carpenter, and a half-dozen other actor-entertainers have followed this recipe with varying degrees of success, producing music that is listenable but not memorable, profitable but not persistent, seductive but not particularly authentic. Think early Monkees, but for today’s short-attention-span audience.

If Carpenter, the former Disney star and current pop phenom, is the modern equivalent of Davy Jones, then perhaps we will have to reluctantly crown Rodrigo as her generation’s Bob Dylan. Since debuting with the surprise hit “Drivers License” in 2021, she has relentlessly curb-stomped every unwritten rule of the Disney pop star, from “don’t seriously discuss sex in your work” to “keep it light or else” to “avoid collaborations with older musicians.” For the past five years, she’s worked a reliable seam of teenage-confessional vocal-fry rap-pop that, like Dylan’s early catalog, taps into an angsty zeitgeist while carefully camouflaging a certain lack of vocal incandescence.

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In a business where people often pretend to be younger than they are, Rodrigo, now 23, has fearlessly and ambitiously engaged with adult themes, unsentimental perspectives, and enough foul-mouthed invective to make a young Liz Phair blush. This material has enabled her to break multiple records for streaming sales and chart position. It has also made her remarkably wealthy because Rodrigo, unlike many of her contemporaries, owns the master recordings of her work.

Think of Rodrigo’s debut, Sour, as the equivalent of The Freewheelin’ Bob Dylan, which makes her new album, You Seem Pretty Sad for a Girl So in Love, eerily reminiscent of Highway 61 Revisited. The common thread here is ambition and a willingness to rock a very profitable boat. Surely everyone from her label to her parents wanted her to make another “Olivia Rodrigo record” and watch the cash register ring. Instead, Rodrigo decided to spin up a pastiche of goth-pop and ’80-style synth-rock that will be utterly novel to her 20-something female audience.

Olivia Rodrigo’s third album is a heartbreaking account of an intense romance and its demise. (Randy Holmes/Disney via Getty Images)

Rodrigo is wearing her influences on her sleeve here, and the most obvious one is the music of Robert Smith and his post-punk band, The Cure. “Drop Dead,” the absolutely delightful synth-popper that opens the album, name-checks The Cure’s 1987 chart-buster “Just Like Heaven” in the first few lines. Another track is flatly named “The Cure.” The icing on the cake, however, is the ballad “What’s Wrong with Me,” performed by Rodrigo with an anguished-sounding … Robert Smith.

The 44-year age gap between Rodrigo and the 67-year-old Smith happens to be the same as the distance between David Bowie and Bing Crosby when they performed “Peace on Earth/Little Drummer Boy” in 1977, but Smith’s energy on both the record and in his recent live performances with Rodrigo frankly exceeds what Bowie and Crosby brought to that Christmas track … combined. Nor is the tune any sort of novelty or joke — it’s already rushing up in the Billboard Hot 100, elevating Smith as a solo artist back to the top of the charts at an age when most people are choosing a retirement community.

Yet this is no soulless nostalgia in the manner of Sha Na Na. Rodrigo has always had a remarkable amount of insight into what her young female listeners want, and she’s been proven right again with You Seem Pretty Sad for a Girl So in Love. Although this record is gleefully rife with synth tones and production techniques that haven’t been common on the radio since the George H.W. Bush administration, she’s writing for a modern audience, not Generation X.

” data-large-file=”https://conservativemodern.com/wp-content/uploads/2026/07/olivia-rodrigos-new-album-defies-expectations-including-her-audiences-1.webp” height=”1024″ width=”1024″ src=”https://conservativemodern.com/wp-content/uploads/2026/07/olivia-rodrigos-new-album-defies-expectations-including-her-audiences-1.webp” alt=”Olivia Rodrigo’s third studio album, You Seem Pretty Sad for a Girl So in Love, was released on June 12, 2026. ” class=”wp-image-4654465″ style=”width:324px;height:auto” srcset=”https://conservativemodern.com/wp-content/uploads/2026/07/olivia-rodrigos-new-album-defies-expectations-including-her-audiences-2.jpg 2560w, https://conservativemodern.com/wp-content/uploads/2026/07/olivia-rodrigos-new-album-defies-expectations-including-her-audiences-2.jpg?resize=150,150 150w, https://conservativemodern.com/wp-content/uploads/2026/07/olivia-rodrigos-new-album-defies-expectations-including-her-audiences-2.jpg?resize=300,300 300w, https://conservativemodern.com/wp-content/uploads/2026/07/olivia-rodrigos-new-album-defies-expectations-including-her-audiences-2.jpg?resize=768,768 768w, https://conservativemodern.com/wp-content/uploads/2026/07/olivia-rodrigos-new-album-defies-expectations-including-her-audiences-2.jpg?resize=1024,1024 1024w, https://conservativemodern.com/wp-content/uploads/2026/07/olivia-rodrigos-new-album-defies-expectations-including-her-audiences-2.jpg?resize=1536,1536 1536w, https://conservativemodern.com/wp-content/uploads/2026/07/olivia-rodrigos-new-album-defies-expectations-including-her-audiences-2.jpg?resize=2048,2048 2048w, https://conservativemodern.com/wp-content/uploads/2026/07/olivia-rodrigos-new-album-defies-expectations-including-her-audiences-2.jpg?resize=696,696 696w, https://conservativemodern.com/wp-content/uploads/2026/07/olivia-rodrigos-new-album-defies-expectations-including-her-audiences-2.jpg?resize=1068,1068 1068w, https://conservativemodern.com/wp-content/uploads/2026/07/olivia-rodrigos-new-album-defies-expectations-including-her-audiences-2.jpg?resize=1920,1920 1920w” sizes=”auto, (max-width: 1024px) 100vw, 1024px”>

Olivia Rodrigo’s third studio album, “You Seem Pretty Sad for a Girl So in Love,” was released on June 12, 2026.

The most obvious declaration of this is the runaway hit “Expectations,” which, despite its Tears For Fears sonic signature, is yet another entry in the currently fashionable pop subgenre best described as “songs about how weak and disappointing today’s young men happen to be.” Carpenter’s newest record is chock-full of this stuff, of course, but it’s all tongue in cheek in accordance with Disney Pop Star Rules. Rodrigo is more direct:

I’m not kissing any boy that is passive
Their indecision is painfully unattractive
Past mistakes are just new information
These days I’ve got expectations 

Social media has collectively lost its mind over another line from the song: “Don’t think my future husband’s at this bar in Silver Lake.” Rodrigo is not alone in striking this non-feminist-approved note; listen to Olivia Dean’s “So Easy (to Fall In Love)” or Carpenter’s “Manchild” for more of the same. It’s both charming and a little heartbreaking to hear young women yearning for old-fashioned love and marriage. Perhaps their generational predecessors should have examined the Chesterton’s Fence of traditional moral and sexual standards a little more closely before driving a VW Bus through it on the way to Woodstock.

Not all of the album evokes the last century. Some of it is clearly influenced by Rodrigo’s counterpart in the prestige side of pop music, the Icelandic Chinese global phenomenon known by the single name of Laufey, including her duet with Smith, “What’s Wrong with Me.” Tracks like “Less” and “Cigarette Smoke” betray a bit of desire on Rodrigo’s part to be a lounge singer and/or symphony solo artist.

Twenty-three is too old for an artist to be considered precocious, so we have to view You Seem Pretty Sad for a Girl So in Love as what it truly is: an intensely ambitious effort that manages to succeed almost without caveats. If one were to throw stones, they would mostly be performance-related. Rodrigo is not capable of persuasively singing all of the notes she can write into a song, but wasn’t the same true of Dylan? It would have also been nice to hear less of the breathless girl-rapping in every tune — it will age like milk, the same way every gratuitous rap verse in a pop song for the entirety of human history has aged like milk, with the sole exception of Debbie Harry’s outro in “Rapture” —  but that’s the opinion of a critic who is very far, in age and outlook, from this album’s core audience.

All early indications are that You Seem Pretty Sad for a Girl So in Love will exceed the remarkable commercial success of its predecessors. It deserves to. Yet the most exciting thing about this album is what it suggests for the future of the artist who recorded it. Rodrigo has the sort of talent that is unlikely to sit comfortably in any one genre for any significant length of time. To persist with the Dylan comparisons, it is easy to imagine her recording the modern equivalent of Blood on the Tracks, or maybe Nashville Skyline. Fair warning to all those young Disney stars who want to follow Rodrigo into stardom: The bar has been raised, and the times, well … they have a-changed. 

Jack Baruth was born in Brooklyn, New York, and lives in Ohio. He is a pro-am race car driver, a former columnist for Road and Track and Hagerty magazines, and writer of the Avoidable Contact Forever newsletter.

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