My Deep Dive Into the Taylor Swift Hype Through The Music: Part 3: Taylor Swift (Debut), Fearless, Speak Now and Red

Becky J Hollen
7 min readMar 24, 2024

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Photo by Brent Ninaber on Unsplash

This was a project that took a while to do considering I had to listen to one artist’s entire archive while holding down a full-time job but an interesting one. Now I have come to the end and in this final phase it’s time for me to decide which Taylor Swift was her at her best, her country years or her pop years? It’s not an easy question to answer unless you’ve done as I have and gone through the entire archive. So, to answer this question I started back at the beginning with her self titled debut album.

Her debut is straight up country and I do listen to country. I got started listening to it when I started working because someone on my shift at the convivence store I worked at always had a country station on. Taylor’s voice and lyrics are very mature for how young she was when she got started. If and when she does re-record this album and I hope she does in order to reclaim the right to the masters, there really isn’t much she has to change to give it a pop vibe if she wants to or just leave it country. I noticed right away that I ran into the same issue with this album that I did with Folklore and Evermore, difficulty in choosing the six songs that stood out but here are the six I finally chose.

  1. Tim McGraw-This is the song that started it all, her first single. She wrote it about her boyfriend who would leave for college and she uses music by Tim McGraw to remember their time together. She would eventually go on to sing the song with Tim McGraw and Faith Hill later on.
  2. A Place In The World — This song is about the unknown future and her hopes for it. I don’t know if she knew back then she would end up where she is now but anyone who listens to it cane gain more confidence about their own futures.
  3. Invisible-Not being noticed by someone you love is rough, especially when they’re with someone else who is probably not the right one for them. This one actually fits a writing project I am working on right now.
  4. Tied Together With a Smile-This one is about someone she knew struggling with an eating disorder and hiding her pain behind smiles. The important thing is seeking help before it’s too late.
  5. Teardrops On My Guitar-This one was about a classmate she was in love with, but that love was never returned but it turns out it was for the best because he was later arrested for abuse. Stil this song can apply to anyone who has an unrequited love.
  6. I’m Only Me When I’m With You-This one is about how someone can truly feel like being themselves with a specific person. It can be a friend, a lover or family. I only feel like I can be myself with my family but when my friend Sharon was still alive, I felt I could be myself with her too.

Now we move on to Fearless. This album was when her popularity really started to grow, and I remembered hearing some of these songs on country radio and liked them. As with her debut there were a lot of songs I liked here and here are the six that stood out. Fearless was her first Album of The Year winner and this one I can honestly say did deserve to win because there were many strong tracks on it.

  1. You Belong With Me- This is another one about loving someone who is in love with someone else and believing you can treat them better. This one also fits my current writing project and was a song I heard at work often that made the night pass a little easier.
  2. Love Story-This is considered her most famous song, inspired by the Romeo and Juliet story but also about trying to get her father’s approval of her new love. This one also fits the story I am writing and was one I enjoyed hearing at night at work.
  3. Fearless-This is another song I heard a lot at work, and I enjoyed how it talked about being brave when entering a new relationship even after being hurt in the past.
  4. The Best Day-This song is Taylor’s tribute to her family and the wonderful memories she has with them, and it makes me think of the happy memories I have with my family.
  5. Tell Me Why-This one is about a relationship that has turned toxic due due to a loved one’s mean streak, and she is asking why she is bearing the brunt of his anger and frustration.
  6. Change-This is a song feels like it is about staying strong in your battle to overcome an obstacle and that a change is going to come if you fight hard enough. It’s also about the joy you feel when it finally does.

Speak Now is the first album Taylor wrote by herself. It seemed that her songwriting ability had come into question, and this was her response. She did have co-writers on her first two albums but that did not mean she wasn’t writing any of the songs because she was and there are lot of strong ones on here but here are the six I chose.

  1. Mine-This one talks about how someone who came from a broken home who fears she’ll end up just like them in her own relationship, but she finds out the man she’s with is willing to fight to keep her.
  2. Sparks Fly-This one is about the chemistry you can have with someone who may or may not be the right person and you decide to take the chance anyway.
  3. Back To December-This was Taylor apologizing to her ex-Taylor Lautner about how their relationship ended. She places the blame for the end of it on herself and that she didn’t treat him well.
  4. Haunted-This one is also about the end of her relationship with Taylor Lautner and how she was haunted by how it ended. It also about how the man she moves onto can’t compete with the memories.
  5. Mean-This is Taylor Swift’s Barracuda-esq response to a critic who wrote a scathing review of a live performance she gave and saying she can’t sang. She is basically saying she’s going to prove him wrong and he’s just going to be mean….I bet the guy is eating his words now.
  6. Better Than Revenge-This is one of her earliest shade songs and the target is the woman one of her boyfriends left her for. She is telling him the new woman isn’t what he thinks she is and sooner or later he is going to get dumped by her.

I’ve now come to Taylor’s last country album Red, where she started her transition from a country singer to pop. I was curious to see if this album like it’s three predecessors followed the same pattern as Folklore, Evermore and Lover where I found so many songs I liked that it was difficult for me to choose six that stood out. It was the same experience I had on those other albums but here are the six I chose.

  1. State of Grace-It talks about the ups and downs of love, but the music style is changing now, there are less acoustics in the production, and it has a more pop feel to it.
  2. I Knew You Were Trouble-This one without a doubt has a pop vibe with the music and it talks about how the boy she likes she knows is trouble, but she falls for him anyway and now deals with the wreckage left on her heart.
  3. We Are Never Getting Back Together-This is about an on and off relationship she decides to end but I hear pre-1989 synth pop music in this one. There are no acustics in this one at all.
  4. All To Well-This is one of the most popular songs among ‘Swities” so I was curious to find out why. This is someone taking a trip down memory lane after a hard breakup and now I understand why it has a such a strong appeal. It is a strong track musically and lyrically.
  5. Red-This song uses colors to contrast the emotions a woman felt in a relationship, passionate red when it was good, blue and gray when it was over. Colors is a theme she will carry into her pop era with Maroon, Cardigan and Lavender Haze.
  6. The Last Time-This is a duet between Taylor and Gary Lighbody about having enough of an off and on again relationship because it has become too painful to deal with now.

The question I had for myself for this project was if the music was stronger in her pop or country era and my answer is that while she did have more songs in her country albums that appealed to me, I wouldn’t consider her pop era weak either and the albums 1989, Lover, Folklore and Evermore are the evidence of this. Her next album, The Tortured Poets Department is due out next month and I do intend to do a review of it. There are four different versions of it expected to be released but I’m just going to take the bonus tracks from the other three and just stick them on the playlist for the main one to make my review a complete one.

This has been quite a journey I have to admit and though I still do not consider myself a “Swiftie”, I just know good music when I hear it and I’ve discovered plenty of it here. Some of these songs I never would have heard were it not for Ariana, my former co-worker and a “Swiftie from Mexico” who gave me the idea to take this trip. Muchas gracias Ariana. I’ve got new music to listen to during a drive, writing or just trying to relax.

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Becky J Hollen

I am an aspiring fiction writer who studies true crime, history and pop culture, giving my own opinions on the matter with snark or without.