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June 8, 2025 16 mins
Welcome back to Hitmaker Chronicles' countdown of the Top 20 Songs of the Summer, as voted by the staff of Caloroga Shark Media! I'm your host, Garrett Fisher. Coming in at number 17, we're diving into Taylor Swift's "Cruel Summer" — a track with one of the most unusual summer song trajectories ever, becoming a massive hit four years after its release. We'll trace how Swift's collaboration with Jack Antonoff and St. Vincent created a masterstroke of summer heartbreak that initially lived in "You Need to Calm Down's" shadow before finding its true audience during 2023's Eras Tour. Grab your friendship bracelets — we're heading into Swiftie summer.

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Unlock an ad-free podcast experience with Caloroga Shark Media! Get all our shows on any player you love, hassle free! For Apple users, hit the banner on your Apple podcasts app. For Spotify or other players, visit caloroga.com/plus. No plug-ins needed!

Subscribe now for exclusive shows like 'Palace Intrigue,' and get bonus content from Deep Crown (our exclusive Palace Insider!) Or get 'Daily Comedy News,' and '5 Good News Stories’ with no commercials! Plans start at $4.99 per month, or save 20% with a yearly plan at $49.99. Join today and help support the show!


We now have Merch!  FREE SHIPPING! Check out all the products like T-shirts, mugs, bags, jackets and more with logos and slogans from your favorite shows! Did we mention there’s free shipping? Get 10% off with code NewMerch10 Go to Caloroga.com


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Transcript

Episode Transcript

Available transcripts are automatically generated. Complete accuracy is not guaranteed.
Speaker 1 (00:03):
Caalaroga Shark Media. Welcome back to Hitmaker Chronicles' countdown of
the top twenty songs of the summer, as voted by
the staff of Calaroga Shark Media. I'm your host, Garrett Fischer,
coming in at number seventeen. We're diving into Taylor Swift's

(00:26):
Cruel Summer, a track with one of the most unusual
summer song trajectories ever, becoming a massive hit four years
after its release. We'll trace how Swift's collaboration with Jack
Antonoff and Saint Vincent created a master stroke of summer
heartbreak that initially lived in You Need to Calm Down's
shadow before finding its true audience during twenty twenty three's

(00:49):
Eras Tour, Grab your friendship bracelets. We're heading into swifty Summer.
Summer twenty nineteen endemic wasn't yet on anyone's radar. Taylor
Swift was navigating her own version of turbulence. Following the darker,
more introspective Reputation era, a period marked by public feuds,
media scrutiny, and her relative retreat from the spotlight, Swift

(01:13):
was ready for her technicolor comeback. The result was lover
her seventh studio album that marked both a return to
brighter aesthetics and a new chapter of artistic control after
her departure from Big Machine Records, and nestled within that
album between the sugar Rush of Me and the LGBTQ
plus anthem you Need to Calm Down sat Cruel Summer,

(01:35):
a song that would have an unprecedented journey from album
cut to cultural phenomenon four years after its release, coming
in at number seventeen on our countdown of the top
twenty songs of the Summer, as voted by the staff
of Calaroga Shark Media, Taylor Swift's Cruel Summer represents perhaps
the most unusual trajectory of any summer anthem, a track

(01:57):
that was summer coded from its creation, but wouldn't have
its true summer moment until half a decade later. Before
Cruel Summer became the delayed hit that dominated twenty twenty three,
Swift was already one of music's defining voices. Since her
two thousand and six self titled debut, she'd evolved from
a teenage country prodigy to a global pop juggernaut, selling

(02:19):
out stadiums and collecting Grammys while maintaining an unparalleled connection
with her fan base. Each album cycle brought not just
new music, but new aesthetic worlds for fans to inhabit,
from the sparkly country pop of Fearless to the eighty
synth pop of nineteen eighty nine. Lover, released in August
twenty nineteen, represented Swift's first album owned by the artist

(02:41):
herself after her highly publicized battle with Scooter Braun and
her former label over her master recordings. This newfound ownership
coincided with a sonic and visual shift away from reputations
darker themes toward a palette of pastels, hearts, and butterflies.
The album's rollout began with the polarizing Me featuring Brendan

(03:05):
Yuriy and continued with You Need to Calm Down, which
became the focus of Swift's Summer twenty nineteen push, complete
with a star studded video featuring a reconciliation with Katy Perry.
But for many fans and critics, it was Cruel Summer,
never released as an official single in twenty nineteen, that
represented the album's pinnacle. Created in collaboration with Jack Antonoff

(03:29):
and Annie Clark better known as Saint Vincent, the track
exemplified Swift's gift for transforming personal heartbreak into universally resonant pop.
So what makes Cruel Summer such an effective summer anthem
worthy of delayed dominance? Let's break it down musically. Cruel

(03:49):
Summer is a masterclass in contemporary pop production, showcasing Antonov's
distinctive touch while remaining quintessentially swift. The track opens with
synthesizers that immediately establish its summer credentials. Bright slightly warped
with an underlying pulse that suggests both excitement and anxiety.
The production builds layers of electronic elements that create a

(04:12):
sonic landscape, reflecting the song's emotional complexity. What distinguishes the
instrumentation is its perfect balance of tension and release. The
verses maintain a simmering restraint with their pulsing sense and
Swift's controlled delivery, while the pre chorus begins building pressure
that finally explodes in the cathartic chorus. This dynamic structure

(04:33):
mirrors the emotional arc of a summer romance that simultaneously
thrilling and torturous. The production incorporates subtle touches that reward
repeated listening, the vocoder effects on Swift's voice in certain sections,
the layered backing vocals that add depth and urgency. The
percussion that drives the track forward with relentless momentum. These

(04:55):
elements create a richly textured sound that feels both contemporary
and time, anchoring the song in twenty nineteen while ensuring
it wouldn't sound dated when it finally had its moment
years later. Most importantly, the production creates a sonic environment
that perfectly complements the song's lyrical themes. The slightly feverish

(05:16):
quality of the synthesizers, the breathless pace of the verses,
the explosive release of the chorus. All these elements musically
embody the intoxicating but painful summer romance described in the lyrics.
The structure of Cruel Summer demonstrates Swift's evolution as a
songwriter and her perfect collaboration with Antonov and Clark. The

(05:37):
song follows a verse pre chorus chorus pattern, but with
several elements that elevate it beyond formulaic pop. The verses
establish the narrative foundations with vivid imagery and emotional detail.
The pre chorus functions as both a bridge to the
chorus and an escalation of the emotional stakes, with Swift's
delivery becoming increasingly urgent. The chorus provides the songs of

(05:59):
momotional and melodic center, delivering both the title phrase and
the track's most memorable hooks. What makes the structure particularly
effective is its culmination in the bridge, a Swift specialty
throughout her career. In Cruel Summer, the bridge represents the
song's emotional peak, with Swift's vocals reaching their most intense

(06:20):
and vulnerable point. This section has become particularly famous for
Swift's delivery of its final line, which she practically screams
in a way that breaks from her typically more controlled
vocal approach. This carefully crafted structure creates a perfect arc
that builds from the tension of attraction, through the complications
of a secret relationship to the ultimate emotional catharsis of

(06:43):
confessed feelings. The journey feels complete, yet leaves listeners eager
to experience it again, contributing to the song's incredible repeatability.
The lyrics of Cruel Summer showcase Swift's gift for detailed
storytelling and emotional honesty. While I won't quote extensively. From
the lyrics to re SSPEC copyright, I can note that
the song portrays a summer romance characterized by both intoxicating

(07:06):
attraction and painful complications. Swift uses concrete imagery, specific locations,
visual details, sensory experiences to ground what could otherwise be
abstract emotional states in tangible reality. The song's central concept
of a cruel summer works on multiple levels. It refers
both to the emotional turmoil of the relationship depicted, and

(07:29):
possibly to Swift's own experience during the summer of twenty sixteen,
which was marked by public controversies. This layering of personal
and fictional narratives has always been one of Swift's strengths
as a songwriter, creating songs that feel simultaneously intimate and universal.
What elevates the lyrics beyond conventional pop romance is Swift's

(07:49):
willingness to acknowledge complexity and contradiction. The relationship depicted is
neither purely blissful nor entirely toxic. It's a messy human
connection that creates both joy and pain. This emotional authenticity
resonates with listeners who recognize their own complicated experiences in
Swift's nuanced portrayal. What truly makes Cruel Summer special is

(08:13):
Swift's vocal performance, which navigates the song's emotional journey with
remarkable versatility. In the verses, she adopts a relatively restrained,
almost conversational approach that draws listeners into the narrative. The
pre chorus introduces more urgency and vulnerability, while the chorus
showcases her melodic gifts with its instantly memorable hooks. But

(08:36):
it's the bridge where Swift's vocal truly shines, building from
controlled emotion to that now iconic final line delivered with
raw intensity. This moment has become so beloved that it
regularly elicits massive audience reactions during the Eras tour, representing
a perfect example of how Swift uses vocal performance to

(08:57):
enhance lyrical and emotional impact. The collaboration with Antonov and
Clark brings out the best in all three artists. Combining
Swift's narrative songwriting with Antonov's gift for both nostalgic and
forward looking production, and Clark's innovative approach to pop structures,
the result is a song that feels simultaneously personal and

(09:18):
universal specific and archetypal, the hallmarks of Swift's most enduring work.
More in a moment, Cruel Summer had perhaps the most

(09:40):
unusual journey of any song on Our Countdown. Despite not
being released as an official single in twenty nineteen, it
became a fan favorite from the Lover album, with many
Swifties arguing it should have received the single treatment. Critics
similarly praised the track, with publications like Rolling Stone and
Pitchfork highlighting it as an album standout. But the song's

(10:03):
true moment would come much later. When Swift launched her
massive Erastur in March twenty twenty three, Cruel Summer was
included in the Lover segment of the show, complete with
elaborate choreography and visuals. The audience reaction to the song,
particularly to the bridge, was so explosive that videos began
circulating on social media introducing or reintroducing the track to millions.

(10:28):
This renewed attention led to an unprecedented chart resurgence. In
July twenty twenty three, four years after its initial release,
Cruel Summer reached number one on the Billboard Hot one hundred,
Swift's milestone tenth number one hit The song also topped
charts globally, becoming a genuine worldwide phenomenon half a decade

(10:49):
after it first appeared. To fully appreciate the context of
cruel Summer, we need to look at both its original
summer of twenty nineteen and its eventual dominance twenty twenty three.
Summer twenty nineteen was dominated by artists like Lil nas X,
whose Old Town Road had an unprecedented nineteen week run

(11:10):
at number one on the Billboard Hot one hundred. Other
chart toppers included Billie Eilish's Bad Guy Shawn Mendes and
Camilla Cabello's Senorita and Lizzo's Truth Hurts. Swift's own You
Need to Calm Down reached number two, becoming one of
the season's defining anthems. The summer movie landscape featured blockbusters

(11:31):
like Spider Man, Far From Home and The Lion King,
While HBO's Game of Thrones concluded its eight season run
to mixed reception. The Women's World Cup captured global attention,
with the US team securing victory in the final against
the Netherlands. Technology continued its rapid evolution, with social media
platforms like TikTok gaining increasing influence in music promotion. Streaming

(11:56):
solidified its dominance of music consumption, with Spotify and Apple
Music becoming the primary ways many listeners discovered new music.
By contrast, summer twenty twenty three, when Cruel Summer finally
had its moment, was defined by emerging from the shadow
of the COVID nineteen pandemic that had dramatically changed life.
Since early twenty twenty, Swift's aristour became a global economic force,

(12:20):
with economists noting its impact on local economies wherever it visited.
The tour's influence was so significant that Swift was named
Times Person of the Year for twenty twenty three, recognizing
both her artistic achievements and her unprecedented cultural and economic impact.
The song's delayed success speaks to several interesting phenomena, Swift's

(12:42):
remarkable longevity and growing influence, the power of social media
to resurrect and recontextualize music, and the increasingly nonlinear nature
of how music is consumed in the streaming era, What
might have once been considered old music can now find
new life and new audiences years after its initial release.

(13:02):
For Swift herself, the belated success of Cruel Summer occurred
within a period of extraordinary productivity and success. Between twenty
nineteen and twenty twenty three, she released five original albums, Lover, Folklore, Evermore, Midnights,
and The Tortured Poet's Department. Ann began her project of
re recording her earlier albums to reclaim ownership of her catalog,

(13:25):
resulting in Fearless Taylor's Version, Red Taylor's Version, speak Now
Taylor's Version, and nineteen eighty nine Taylor's version. This creative output,
unprecedented for an artist of her stature, further cemented her
status as one of her generations defining musical voices. The
song's influence extends beyond Swift's own career. Its production style,

(13:49):
blending electronic elements with emotionally direct lyrics, has informed countless
pop tracks that followed its journey from album cut to
delayed hit. Has created a new model for how songs
can chief success in the streaming era, potentially changing how
artists and labels approach single selection and promotion. More broadly,
Cruel Summer exemplifies how summer anthems can address the season's

(14:12):
complexities rather than just its celebrations, by acknowledging summer's capacity
for emotional turmoil alongside its pleasures, the song creates a
more honest and ultimately more satisfying seasonal anthem than those
that focus solely on good times. Looking back on Cruel
Summer today, it remains remarkably fresh, despite being written in

(14:32):
twenty nineteen and finding its biggest audience in twenty twenty three.
The song's emotional honesty, musical innovation, and perfect execution have
allowed it to transcend its original context to become a
timeless expression of summer's emotional extreme. What makes Cruel Summer
the quintessential modern summer anthem is its recognition that summer

(14:53):
isn't just about care free joy. It's also about heightened emotions,
complicated relationships, and experienceiances that can be simultaneously wonderful and terrible.
This emotional complexity, combined with production that sounds like summer feels,
creates a track that resonates with anyone who's ever had
a season marked by both sunshine and storms. So, as

(15:15):
we continue our countdown of the top twenty songs of
the Summer, at number seventeen, turn up Cruel Summer and
let Taylor Swift's perfect pop storm reminds you that the
most memorable summers aren't always the happiest. They're the ones
we feel most intensely, for better or worse. Because Cruel
Summer isn't just a song. It's proof that great music

(15:37):
finds its audience eventually, a testament to Swift's unparalleled ability
to transform personal experiences into universal anthems, pen a reminder
that Summer's magic lies partly in its emotional extremes. Years
after its creation, it continues to capture that complex summer
feeling with remarkable precision, which is why it deserves its

(15:58):
place in our summer song's pantheon. This is Garrett Fischer
for hit Maker Chronicles, counting down the top twenty songs
of the Summer, as voted by the staff of Calaroga
Shark Media. Trade those friendship bracelets and join me next
week as we continue our countdown with number sixteen.
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