Taylor Swift's 20 Greatest Songs

by Tyler Glover
When we turn on the radio on the way to work, we hear music that is seeking to connect with us. The intention behind the connection could be solely just to make money and “hits.” It seems many music producers nowadays appear to only be interested in finding that hook or beat that will have people’s heads bobbing regardless of the substance of the lyrics. But, there are times when you hear those songs that touch you. These songs tell stories that reflect the human experience. What does it feel like when you have your first kiss? Your first heartbreak? What does it feel like when you love someone that doesn’t love you in return?How does it feel to lose someone?

I was 19 years old when I first heard the music of Taylor Swift. At the time, I was in love with a girl that was never going to love me in return. She was in love with someone else and I never stood a chance. I got in my car one day very upset about the situation and heard Taylor Swift for the first time. The song: “Teardrops on My Guitar.” I immediately started crying because the song comforted me in feeling that I was not alone. There are other people that have been through the same experience and now I could listen to this song and feel sad and let my emotions overtake me while hearing the story of my situation play out in song.

Ever since then, in a lot of ways, I feel that Taylor Swift has written the story of my life while writing the story of hers. She writes her own music and tells the stories of her life and in some ways, gives a voice to my own. Listening to her music takes me back to all the happy and sad times that I have had in my life. Sometimes, when I am having a bad day and feel I am being picked on, I can listen to songs like “Shake It Off” and “Mean” and instantaneously feel better about everything going on. Music makes you laugh and it makes you cry but most importantly, great music will make you feel something. When listening to Taylor’s music, I have smiled, laughed, cried, gotten angry, felt remorseful, felt right and I have felt wrong. The way that I connect with Taylor Swift’s music is not how everyone will connect with it. We all have our own individual experiences that are unique. You may listen to George Strait, Michael Jackson, Tina Turner, Madonna, Janet Jackson, Lady Gaga, or Katy Perry and feel the same way I feel about Taylor. That is what is so great about music. It touches all of us in different ways.

I wanted to start with this discussion because I am going to rank my top 20 Taylor Swift songs. All the songs that round out my top 20 are not there because of a hook or a catchy beat. They are there because of how they made me feel and continue to make me feel.

​Here is my list of the top 20 Taylor Swift songs (so far). 

---

20. “Look What You Made Me Do”
A lot of people have criticized this song because they feel we are responsible for our own actions and nobody makes us do anything to which I completely agree. First off, I love that music is an art form that is open to interpretation. When I hear this song and rock out to it in my car, I think about how people can choose to treat you how they are going to, but it is not free from consequences. You may not trust them if they hurt you. You may be able to forgive but not forget. It changes the dynamic of the relationship. You still could even be following the golden rule with this person but if you look at what they did, you must make decisions in your life to where you protect yourself from it happening again. So, look at the decision you led me to make is how I see it.

In this song, Taylor Swift acknowledged that she got out of the public eye because of the constant scrutiny she was under and the constant attacks on her... um, reputation. 

19. “Red”
Speaking of how Taylor Swift’s music really deals with all kinds of relationships, I feel this song is representative of all the emotions that go on during relationships. Taylor Swift finds the perfect way to describe a relationship with the color red. In relationships, there is love, there is passion, and there are those moments when your partner makes you see red with anger. My favorite line in this song is “Loving him is like driving a new Maserati down a dead end street.” Relationships and life in general can be a rollercoaster and you want to make sure you are with the right person. I love this song because Taylor makes you acknowledge that it is not always a fairytale. There are sometimes, you feel like you are going to crash and burn. It is what we do about it that counts. 

18. “White Horse”
In this heartbreaking song, Taylor is at the end of a relationship upset with herself that she did not know better. She thought this relationship was some sort of fairytale, but you just feel so devastated for her when she sings “I’m not a princess/This ain’t a fairytale.” This song came out right after “Love Story” did and it was literally the opposite of what “Love Story” was. It definitely helped to show Taylor’s range and that to her, she did acknowledge that life was not full of happy endings like her other songs suggested she believed.

When relationships end, sometimes, you have that person trying to get back together with you and it is not something you can shrug off and listen to “We Are Never Ever Getting Back Together” and feel better. Sometimes, it is more painful than that It depends on the relationship you are in. Therefore, Taylor’s music touches me in my life so much. It is because she has music that deals with all the different kinds of emotions that go into the construction and demolition of a romance. Taylor knew better than to allow him to ride in on his white horse and think they could fix it. It was time for him and his white horse to ride along somewhere else.

17. “Last Kiss”
This is such a tragically beautiful song where Taylor talks about how she never thought she would have a last kiss with this man. She never thought it would end. When listening to the song years later, it even feels like it could apply to multiple situations in life such as even the death of a significant other. I was re-listening to this song recently and it made me get misty eyed because I started thinking about how one day, I will have a last kiss with my wife. This will be either because she will pass away or I will pass away but there will be a last kiss. It is heartbreaking but at least, we have that love until the end. In this song, though, Taylor is devastated because she felt she had the real deal but sadly, they said goodbye with one last kiss.

16. “Dear John”
One thing about “Dear John” that amazes me is that this song is six minutes long and I still do not want it to end when it does. Taylor is writing this song to let her former beau know why she stopped picking up his phone calls. She is very candid about how he made her feel and how he hurt her. It is also the most direct mention of who her song is about since the song is rumored to be about John Mayer unless you count that the song “Style” is rumored to be about Harry Styles.

There are two parts to this song I especially love. The first one is when she says she is “wondering which version of you I might get on the phone tonight.” Sometimes, in relationships, you have that person who is one way with you one day and totally different the next. You never know what you are going to get with this person. My second favorite lyric is when she says, “the girl in the dress wrote you a song/You should’ve known.” At this time in her career, she was just starting to become known as the girl who writes about her boyfriends. This lyric was like “Blank Space” in that she was owning that persona the media was giving her.

15. “Enchanted”
This enchanting song captures the magic we experience when we first lay eyes on that special someone. Taylor sings about being in a room where she is “forcing laughter” and “faking smiles” when suddenly, it vanishes when she sees him. She sings about how she is enchanted to meet him and how she does not want the moment to end. This song just takes you back to this special moment and how you never wanted it to end. You wanted the moment to last forever because you did not want to let the feeling go. Even eight years later, it is still enchanting to hear “Enchanted.”

14. “Mean”
Taylor wrote this song in response to a particular journalist who proclaimed that her career was over because of a “horrible” performance at the Grammys. Taylor had performed with Stevie Nicks at the 2010 Grammys and this journalist felt her career could not recover from it. Taylor sings about how they “can take her down with just one single blow” but what they do not now is that someday, she will be “living in a big old city” and all they “are ever going to be is mean.” She lets them know her future is bright. You can learn from your experiences and make yourself better, but if you go through your life as a heartless bully, that is all you will ever be.

When I hear this song, I think about how I have been cut down and made to feel like I was nothing before. I think we have all had those experiences and when listening to this song, it makes me feel better almost instantaneously.

I also think that this song, even though written years ago, can make a statement about our culture right now. People will go on people’s Facebook, Twitter, Instagram, or any social media outlet and use it to belittle or put people down. It is something they may not feel comfortable to do in person, but one negative thing about social media is it does give a voice to bullies to feel more empowered. When writing this song, Taylor is not worried about it. This song makes you feel empowered to stand up to those people and make them realize that their opinion does not matter to you. You know what I mean?

13. “Begin Again”
Most of Taylor Swift’s songs chronicle the magic, the love, the heartbreak, the mistakes, and the moments where we decide to pick up the pieces and move on. When writing “Begin Again,” Taylor was coming off a breakup that was so damaging that it was taking months to get over. She sings, “I’ve been spending the last eight months/Thinking all love ever does is break and burn and end.” It is such a heartbreaking song in some ways, but also very hopeful because she meets a guy “on a Wednesday at a café” and watches it “begin again.” 

One of the moments of this song I feel we all can relate to is when she mentions that she almost brings up the old boyfriend in conversation with this new guy she is dating but then he mentions something that causes her to forget to mention the former beau. I really connect with this because I have had those relationships where I was so in love that when first dating again, it was almost impossible not to bring them up because they were a part of my life’s journey that I was experiencing the past few months whether the other person was or not. For example, I was still trying to get over them while they were very happily moved on. My time finally came when I found someone that helped me to begin again. I am so grateful God put her into my life and when I hear this song, I think about the moment I met her and how she helped me recover my broken heart, so I could love again…so I could begin again.

12. “Back to December”
This song was drastically different than any other Taylor Swift song when it first came out because for once, she was taking the blame for a relationship ending. She sings, “This is me swallowing my pride/Standing in front of you/Saying ‘I’m sorry’ for that night/And I go back to December all the time/It turns out freedom ain’t nothing but missing you/Wishing I’d realized what I had when you were mine.” It was a very heartbreaking song rumored to be about the end of her relationship with “Valentine’s Day” co-star Taylor Lautner. It is not that Taylor Swift has not claimed to have been part of the reason for the relationship failures in the past; it was just that the songs were meant to deal with her feelings regarding them and in some cases, for the song’s purpose, it was irrelevant who was to blame.
​
This song really makes the listener feel empathy for her because we all have hurt someone sometimes, inadvertently in a relationship that led to its end and then we immediately realize the mistake we have made. Sometimes, the damage is done though, and all there is left to do is dwell on what was and what might have been until that moment where we can move on. 

11. “Sparks Fly”
“Drop everything now. Meet me in the pouring rain/Kiss me on the sidewalk/Take away the pain/’Cause I see sparks fly whenever you smile,” Taylor sings. Taylor is so fantastic at making music feel magical. This is a song that is reminiscent to “Fearless” to me in that, it is talking about spontaneous moments that make a relationship special. It could be a big event like a special date or just a simple look with their eyes. This song is a song I play every Fourth of July when the fireworks are going off because at one point, she uses a firework show as a comparison to their relationship. Fireworks during Independence Day is a celebration of our freedom from British rule and when listening to “Sparks Fly” on this day, Taylor reminds me with this song that we need to celebrate love.

10. “Innocent”
This song Taylor wrote in response to Kanye West interrupting her during the MTV Video Music Awards in 2009. It was not what we expected her to write regarding this situation. You would have thought she would have been very angry because after all, she had won the award for Best Female Music Video for her song, “You Belong with Me,” and the rapper, Kanye West, interrupted her to say that she did not deserve to win because Beyoncé Knowles did for “Single Ladies.” It is not what she expected that night either but instead of coming at him, guns blazing, like she will later do in “Look What You Made Me Do,” she sings that we are not who we are because of one mistake. We are not perfect human beings and the most powerful lyric in this song is where she sings: “Who you are is not what you did.” We all have done things that we feel awful about and when we think back on it, we could make ourselves believe we are horrible people who are undeserving of a second chance, but we cannot dwell on it. Taylor sings, “Today is never too late to be brand new.” We may not always be perfect, but we can always strive to do better in our lives. This song is such a nice, friendly reminder that we can use those times as learning experiences to help us grow into better human beings in the future.

9. “Teardrops on My Guitar”
I do not play the guitar, but I have shed lots of tears while listening to this tear-jerking ballad. Taylor is in love with this boy who is in love with someone else. She has not told him how she feels about him because she wants to be the good girl and allow him to be happy with the girl that he cares so much about, but it is at the expense of her own happiness.

As I mentioned earlier, this is the first song I ever heard of Taylor Swift’s and it came at a time of much heartbreak. I was in love with a girl who didn’t love me. It is very hard to move on when you feel that person is the one. I felt like we “clicked” so well and wanted it to work but she didn’t. It took me about a year to finally accept it and move on. It truly was my first heartbreak and there were moments I wanted to feel terrible and feel the pain I was going through in music and this song provided that outlet. I did not feel alone. Even people as beautiful and famous as Taylor Swift experience this heartbreak. This song was the very first connection that I made with Taylor Swift, with teardrops. 

8. “Fearless”
“And I don’t know why but with you, I’d dance in a storm in my best dress/Fearless,” Taylor sings. I absolutely adore this song. Today, in our world, there are a lot of people who are planners. They follow schedules and live by them. I am certainly one of these people, but I love the spontaneity that Taylor sings about in this song. I have gone outside when I have seen it raining and taken my daughter with me while playing this song on my sound system. It is simply a magical feeling. To see my daughter’s beautiful face giggling and laughing while we spin around in the rain is simply magical. This song inspired me to take advantage of moments like these. Finding those moments in life where you do something you typically wouldn’t do. It is so freeing. You are finding simple ways of rebellion to the way that our society seems to function nowadays. I am so thankful for this song, because without it, there may not have been simple moments like this where I was fearless.

7. “Ours”
This song is very near and dear to my heart. In this beautiful song, Taylor sings about how she goes to work but does not want to because she wants to be spending time with her man. She talks about how it sometimes feels like people disapprove and they try to judge, but they don’t know about the relationship these two people have.

This song holds one of my favorite Taylor Swift lyrics of all time: “Don’t you worry your pretty little mind/People throw rocks at things that shine and life makes love look hard/The stakes are high/The water’s rough/But this love is ours.” When I hear this song, I don’t only think about the bond I have with my wife but the bond I have with my kids. When she is singing about how her time at work is theirs and how she wishes she could be with him, I feel the exact same way about my kids. I always want to be soaking in all the time that I can with them while they are young. When I hear this song, I feel happy that I have the time I have with my kids but sad to know that the time is fleeting. I try to spend as much time with them as possible because one day, their time will be spent mostly away from me, but right now, this time is ours.

6. “We Are Never Ever Getting Back Together”
“We are never ever, ever getting back together. Like ever,” Taylor sings. In this song, Taylor sings about how she has this boyfriend who cannot seem to take a hint that the relationship is over. He is holding onto hope that they can work things out, but she is done with the relationship and wishes he would be to. It has real funny lyrics. She sings, “I’m really gonna miss you pickin’ fights and me falling for it screaming that I’m right.” The tone of the song is very light-hearted even though it is tackling something as serious as the end of the relationship.

I find this song very funny every time I listen to it because I have always been the one in relationships that has been very hard to let go. I don’t want to believe it is over; I always want to believe that if two people are willing, then the relationship can work. This song points out though that it does take two people because whereas, I was wanting to work it out, the girls I have dated were not wanting to work it out. Like…ever.

5. “Shake It Off”
Taylor Swift has always had to deal with her fair share of critics that just constantly tried to make her feel that something was wrong with her. She was too needy, too obsessive, too self-absorbed, too fake, too pretty, too “nice,” too boy-crazy, and the list goes on and on. This song is such a feel-good song to sing and dance to when you are feeling like you have people like this in your life. There are those days where you feel people just constantly put you down for you just being who you are or for what their perception of who you are is. Taylor sings that we need to shake it off and forget about the haters. We need to dance to the beat of our own drum. This is such a great definition to me for what music is. It makes you feel happy and sends out such a positive message as well. It does make someone feel good to know that even people like Taylor Swift have issues like this in her life. We are not alone, and Taylor makes us realize we are not.

4. “You Belong with Me”
This story that Taylor Swift depicts is something I think we all have dealt with before. She is in love with a boy that is with another girl who doesn’t treat him the best. It is a very upsetting situation most of the time because you know that if you were given the opportunity, you would treat this person so much better than this person who constantly takes him for granted. She talks about the differences in them: “she wears high heels, I wear sneakers, she’s cheer captain and I’m on the bleachers.” She is “dreaming about the day when [he] wakes up and finds that what [he’s] been looking for has been here the whole time.” It is such a sweet song with a sweet fairytale ending where she officially finds out that all this time, he has loved her in return.

When men choose to propose to the one that they want to be with, they always try to find some special way to do it. I have always loved to sing, and I decided to sing this song to my girlfriend at the time. At the end of the song where Taylor sings “Have you ever thought just maybe, you belong with me?/You belong with me,” I changed the lyrics to say “Have you ever thought just maybe, you belong with me?/So will you marry me?” As I started going into the marriage proposal, I pulled the ring out of my pocket and opened it up. I still remember the tears from my wife. She cried for the longest time before finally getting her composure to tell me “yes.” She did belong with me and this beautiful song belongs in my top 20 of Taylor Swift songs.

3. “Love Story”
This song truly depicts the joy of being in love. When you love someone, it doesn’t matter who is against you. You feel you are meant to be together and nothing is going to stand in your way (even if it is dear old daddy). Taylor knows how to make songs into a whimsical fairytale romance. She says that “you’ll be the prince and I’ll be the princess. It’s a love story, baby, just say yes.”

This song is very special to me because when they announced my wife and I as husband and wife, this is the song that the DJ played. Every time I hear this song play, I remember holding my wife’s hand and walking into a room full of people who loved us and was helping us celebrate the love that we had for each other. This song also has resonance for me because I thought her father hated me for years. Something I think most guys can relate to. 

2. “All Too Well”
In “All Too Well,” Taylor writes about that feeling when the relationship is over, and you are trying to move on. She remembers a specific day when they went to his sister’s house and she left her scarf that he still has to this day. She remembers those sweet moments that happened there. She remembers him telling her about his past. One thing that resonates so much to me is when she sings “you tell me about your past thinking your future was me.” When I hear that, I think about all the time that we all spend investing into relationships. In the end, you can feel cheated in some way that all that time is gone now. All the conversations with someone to make that connection are all for naught. Sometimes, in relationships, we give so much of ourselves that we wonder what is left when it’s over. Taylor sings: “Time won’t fly/It’s like I’m paralyzed by it/I’d like to be my old self again/But I’m still trying to find it.”
​
I have certainly been in this same situation. There was a girl that I loved so deeply and felt she was “the one” for me for a long time. When I finally came to the realization that nothing I was going to ever do was going to be good enough for her, I didn’t know what I was going to do. I felt she was the one for me so how could there be anyone else? And yet, for me to experience love, that is how it was going to be, but I would first have to find myself again before I could move on.

1. “Blank Space”
Taylor wrote this song to address the fact that the media was portraying her as a crazy, boy-obsessed stalker. She was dating like a normal young woman in this world. If she wasn’t a celebrity, no one would have thought anything about the fact that she dated several men. After all, it does not mean they were sleeping together. Sometimes, you have to date several toads before you find your prince. The media was having a field day though. They constantly put headlines that portrayed her in a negative light. In this song, rather than ignore those allegations, she decides to portray this character that the media was assigning her. Who is Taylor Swift? She tells us that she is a “nightmare dressed like a daydream.” Knowing the intention of her writing this song just makes that lyric so much sweeter every time you hear it.

When I hear this song, I think about the times in my life where I have felt that I have been misunderstood or been characterized as something I’m not. I have a very feminine voice and do not have the interests of typical men nowadays and those things have led many to think that I am gay when in fact, I am not. It is something that affects me every time I meet someone new. There for a long time, I was more shocked if when meeting people that they originally thought I was straight. This song helps me to feel better about all those times.