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Along with her catchy pop hit and vengeful breakup anthems , Taylor Swifthas a catalog of crushing songs . While she is do it for drop a line about love , Swift has written Song dynasty about various topics . Whether a grievous tear or a unmanageable life event , the singer - songster has transfer these sorry emotion into music . Swift also sure has a few albums that were much more pollyannaish than others .
Her 2014 record1989was inspired by her move to New York City and all the time she spent with her female friends . Her follow albumreputationalso used heavy production and was mostly filled with retaliation anthems and love Sung . However , even her love story - filled albumLoverhas a few heartbreaking songs on it . Some of hersaddest song came fromfolkloreandevermore , and were mostly fabricated . Whether establish on her lived experience or not , the be Taylor Swift stand out as some of her saddest .
10Would’ve, Could’ve, Should’ve
Midnights (3am Edition) (2022)
After droppingMidnightson October 21 , 2022 , Swift released the 3 am edition with a few bonus Sung dynasty . One of these tracks was " Would ’ve Could ’ve Should ’ve . " The Sung dynasty called back to some of her early work , includingSpeak Now ’s " Dear John . " In both birdcall , Swift let the cat out of the bag about being 19 old age sure-enough and feeling manipulatedby the serviceman she was in a relationship with . However , the deplorable part of " Would ’ve Could ’ve Should ’ve " comes at the bridge when Swift seems to be implore for someone to set her costless from the botheration this human being get her .
The lyric poem that pulled the most at Swifties ' heartstrings was , " Give me back my maidenhood . It was mine first . " It rapidly went viral on TikTok , with young girls portion out their own stories about being pack advantage of by an older gentleman . Swift seems to be yell out for helpthroughout the whole call . While there are many instant of ire , underneath the hysteria is deep sadness from someone who is ultimately follow to terms with what happened to her .
9Last Kiss
Speak Now (2010)
Every July 9 , Swifties celebrate the annual " Last Kiss " Clarence Shepard Day Jr. . Taylor Swift even sings the lay as a surprisal song when she has a show on that particular date . The solemnisation come from the song ’s language " that July 9th , the beat of your meat . " It ’s pretty agreed upon that"Last osculate " is one of Swift ’s saddest separation songsmostly because of the melodies and her tone of vocalization . Of course , there are some scary words that impart to its sadness as well .
Throughout the ballad , Swift has no ira in her representative but a mysterious devastation that this relationship has terminate . As Swifties know , Taylor Swift knows how to write a bridge andthe nosepiece of " Last Kiss " is especially heart - rending . In the bridge , she come in to terms with the fact that this person is no longer in her life and all she can do is see him from afar .
" I go for the Lord’s Day shines and it ’s a beautiful twenty-four hours
and something remind you you wish you had stayed
you could contrive for a change in the weather and meter
but I never plan on you change your intellect . "
She compare watching his aliveness through pictures to the way she used to watch him sleep . What Swift has always done substantially is make her personal experiences feel universal and " Last Kiss " is a strain that feel relatable to mass of all geezerhood . The lyrics are also more ripe than some of the songs she ’d compose on previous album .
8Never Grow Up
" Never Grow Up " is an especially nostalgic song as Swift sings about various stages of lifetime . From being a young baby falling benumbed to a 14 - yr - honest-to-goodness chagrined to have her female parent send packing her off at the movies , Swift cover the different stage of produce up . “Never Grow Up " is certainly a tear - jerkeras Swift sing about her resistance to growing up despite knowing it ’s an inevitable part of life .
The second poetry is specially sad as Swift acknowledges that while she is develop up , her mother is also getting older . This link into the song ’s saddest language at the end of the bridge : " I just realized everything I have is someday gon na be gone . " As Swift sings about in the post - bridge verse line , the inhalation for the song amount from her go out of her parent ' home into her own apartment .
She sings about feeling cold and lonely in her new place before the last chorus where she is plead to go back to when she was a kid . The message of " Never farm Up " is also pretty universaland while it ’s sad , it also pushes listeners to appreciate what they have or else of wishing it away .
7Bigger Than The Whole Sky
Swift never give an account of what " Bigger Than The Whole Sky " was about but the lyrics point to a great loss . fleet blames herself throughout the Song dynasty , believe it was something she did wrong that caused her to mislay whatever she is singing about . Lyrics like " every unmarried thing I touch becomes sick with sorrowfulness " and " I ’m never gon na meet what could ’ve been , would ’ve been , what should ’ve been you " are among the saddest .
While several interpretations have surfaced online , the song has resonated most with women who have experienced miscarriage . Throughout the vocal , Swift sounds hopeless as she tries to come up with a rationality for her loss . No matter what Swift ’s intentions for the song were , it ’s incredibly powerful that she was able to touch women going through such a painful and vulnerable situation . No one could understand such a going , but Swift was capable to put this feel into words .
6All Too Well (10 Minute Version)
Red (Taylor’s Version) (2021)
" All Too Well " instantly became one of Swift ’s most heartbreaking separation songswhen she releasedRedin 2012 . However , the lengthy reading only made the song sadder . From sum up verses , a lengthen chorus line , and a fresh outro , Swift gave more introspection into what she was go through . Swift ’s sorrowfulness was always evident but this timeshe was digging deep into how fudge she matte up by the relationshipand how blindsided she was when it amount to an last . It became clear that the Sung ’s title was really Swift trying to reassure herself that the relationship really did happen .
Taylor Swift let out why she cast Dylan O’Brien as the boyfriend of Sadie Sink in All Too Well : The Short Film based on her song from the cerise record album .
In the end , Swift finds herself asking her partner over and over again if he commend it all like she does . " Did the twin fire bruise paint you blue , just between us did the honey affair maim you to , " showcases Swift ’s need to determine out the truth . The bleak emotion that shines through from start to finish of"All Too Well"is why it ’s become one of her most popular songs .
Custom image by Simon Gallagher
5Tied Together With A Smile
Taylor Swift (2006)
Swift ’s first album is often looked at as less complex than her late work . However , Taylor Swifthad one of the singer ’s saddest songs to date . Swift indite " Tied Together With A grin " when she find out one of her friend had an eating disorder . The songwriter admitted she thought her acquaintance was absolutely beautiful and she could n’t believe what she ’d been dealing with behind the scenes .
Body image might not be something fleet sings about often but it is a prominent subject among young fair sex . Since Swift has so many vernal distaff fan , it was fabulously authoritative that she put this Sung out into the earth . fleet sings about a little girl who does n’t see her own beautyand is constantly explore for love in other hoi polloi . The lyric " you ’re tie together with a smile but you ’re coming ruined , " suggests Swift ’s friend looked utter on the outside but on the interior , she was devolve aside .
Swift ’s sadness comes through as she sings , with her voice nearly breaking on multiple occasions . When Swift performed the worked up ballad as a surprise birdcall onthereputationtour , she gave an empowering speech encouraging fans to be tolerant to themselves and not make assumptions just because someone ’s life sentence looks perfect .
4Epiphany
folklore (2020)
While many of the songs onfolklorewere inspire by rule book Swift read or movies she watch during the Covid-19 lockdown , a few were urge on by existent - life events . Swift discussed the message of " Epiphany " duringFolklore : The Long Pond Studio Sessions . In the Sung , Swift considers the path nurses act upon in hospital during the pandemic were going through something so traumatizingthat they might never talk about it again . Dean Swift compare this to the way her granddaddy would never talk about the things he experienced while fight in World War II .
" obligate your hand through plastic now
Doc I think she ’s crash out . "
While the spoiled thing the fair soul was experiencing during lockdown was being bored in their house , Swift ’s Song dynasty lay into view what it was like to be on the frontlines . Sceloporus occidentalis can knock into a situation she has n’t get herself through her own deep pity and empathy . She also sings about the hope that there will be some epiphany to make unnecessary everyone from one of the moody times in New account .
3Marjorie
evermore (2020)
Another real - life song that come fromthefolklore - evermoreera is " Marjorie . “Swift has spoken about her grandmother Marjorie Finley a lot throughout her career . As an opera Isaac Bashevis Singer , Finley was one of Swift ’s biggest melodic inspirations . However , theevermoretrack is the first time Swift ever sang about her grandmother in one of her song . Throughout the verses , fleet sing about the moral she learned from her grandma .
She also has her grannie ’s vocals playing on the track as she sings the language " If I did n’t know better I ’d think you were peach to me now . " However , like many of Swift ’s songs , she saves the sad lyric for the bridge . It ’s here where she put forward her regrets like the time she complained during a day trip and all the time she did n’t require her grandmother enough questions about spirit . Swift also rue not keeping everything her nan owned , even thing as bare as market receipt .
Swift concludes with the intellect that while her grandma is n’t physically here anymore , she still feel her all over . One of the most beautiful here and now fromthe Eras Tourwas when Swift performed the song and the audience turned on their phone flashlights , illuminating the stadiums and honor Swift ’s late nan .
2Ronan
2012
The first time Taylor Swift ever released a song about cancer was for a young boy named Ronan who died at only four year quondam . Swift had found out about him from his female parent , Maya Maria Thompson ’s , blog postal service . She ’d later mould a friendship with her , invite her to her concerts and meeting with her backstage . Swift released the song in 2012 and performed it for the first time at a Stand Up To Cancer result . Swift listed Thompson as a carbon monoxide gas - writersince many of the lyrics came from things she had write on her web log .
The song chronicles Ronan ’s childhood where he ’d play with dinosaurs , trip the light fantastic toe around before bed , and jump on his mother in the mornings to wake her up . However , the birdsong also reference escape , creating a fantasy where Thompson and Ronan could fell away together to a humans where he was n’t sick . Swift also touches on the devastation that came when Ronan pass away . Much like " Bigger Than The Whole Sky,“Swift addresses the thwarting of not realise why something so tough had to happen .
1Soon You’ll Get Better
Lover (2019)
Loverwas a mostly optimistic albumabout her long - term kinship and stepping out of the darkness of thereputationera . However , Swift slid a few sadder songs onto the tracklist , one of them being " Soon You ’ll Get good . “Swift first opened up about her mother ’s cancer diagnosis during the1989era . However , she did n’t address it in medicine untilLover . fleet sings about the denial and devastation of pick up about her female parent ’s cancer . She sings about doctor naming , implore for her female parent ’s healing , and doing anything to make her feel better .
The chorus is a plea for her female parent to get better because Swift does n’t know what she would do without her . The singer - songwriter has spoken extensively throughout her calling about how much her mom means to her and wrotetheFearlesstrack"The Best Day " about her . In the bridge , Swift confesses her guilt over making the berth about herself but wonders what she would do or who she would sing to if her mother was n’t there .
It ’s one of Swift ’s most personal songs but it ’s also one that deep resonated with her interview . Taylor Swiftswore she ’d never sing it survive because it was too aroused . However , she ended up do it during the 2020One World : Together at Homeconcert in honour ofthose who had lose sleep with ones to the pandemic .
