Today I am going to be sharing my Top 20 favourite Taylor Swift songs – spanning from her very first album to her latest. What I love about her music is how it speaks to people in various ways. All of us have related to her lyrics at some point in our lives. My experience with her songs will be completely different to yours. I also appreciate that she shares her innermost thoughts and feelings with us; like a diary entry put to a melody. Taylor is known for including hidden messages and Easter Eggs in her words. Fans enjoy deciphering the clues within. If you want full album breakdowns, I highly recommend the YouTube channel: Chats and Reacts. I’ve learnt so much from them about what Taylor is really trying to say. Once you understand the story, the listening experience is so much more powerful. A lot of these songs are ones I deeply relate to. Others, I just love for what they are. Finally, if you want to discover your own Top 20 faves but don’t know where to begin, I recommend taking this test. I had already written up mine prior but decided to take it anyway and got the same results! Without further ado, let’s get into the list!
I think Delicate might be my favourite song of hers – period. If you weren’t aware, on every single album Taylor has ever released, she places her most vulnerable song on track #5. In this number, she expresses what it feels like to be at the beginning of a relationship that you really want to work out. We are able to deduce that she is referencing her blossoming relationship with current long-term partner: Joe Alwyn. It’s also the first time she associates the words blue and dive bar (where they met) with Joe. This trend continues in future songs to let fans know she is singing about him. The film clip is superior too. I have definitely related to this song in the past but I love it now for the melody and lyrics. After everything that went down with Calvin Harris and the drama with Kanye West, Taylor disappeared for a year; not talking to anybody. She returned with Reputation and showed the world through this album how those experiences changed her. With her reputation at an all time low, she tells us that Joe must like her for her and that feels too good to be true. RELATABLE!
2.) Teardrops On My Guitar
Let’s go back to the very beginning now, when Taylor released her first album at just 16 years old; her innocent, country era where the world began to learn her name. I have mentioned this on my blog before but I’m a huge sucker for early Taylor. I listen to this album the most alongside Reputation and Folklore. This song is a love letter to her former classmate Drew Hardwick, whom she had an unrequited crush. They were friends, but he had a girlfriend at the time, so she had to pine for him through her music. It reminds us of simpler times when our biggest problems were not being noticed by a cute guy. You can really feel her teenage angst. Interestingly enough, Taylor dodged a gigantic bullet in Drew. In 2015, he and his wife were arrested on charges of child abuse. In her song Lover, Taylor croons: with every guitar string scar on my hand, I take this magnetic force of a man to be my lover. Some fans believe this is her way of saying that all the teardrops and scars were worth the build-up to meeting Joe. Drew who?
3.) Back To December
This is the first song on the list that I can relate to. Back when my ex-boyfriend and I broke up, we continued to see each other off and on until we finally called it quits in December for good. I’m obviously over it now but back then, this song got through me some pretty big heartbreak. Taylor has been spurned by many lovers in her time but in this song, she is telling us that she was in the wrong. It’s believed to be about former beau: Taylor Lautner. Who hasn’t half sung/half screamed these lyrics in the car? So 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…
4.) My Tears Ricochet
Welcome to another track #5 song. Some say Folklore is an entire album of them. I have to agree. It is a mixture of story-telling and Taylor processing the loss of her albums to Scott Borchetta and Scooter Braun. My Tears Ricochet is purely about Scott, her former manager who deeply betrayed her when he sold her life’s work to Scooter – a producer she never respected nor liked. This entire song revolves around a funeral theme; mourning the death of a relationship with a man she thought would never hurt her. It’s HEARTBREAKING. The music, the lyrics, the bridges, the melody changes…everything about it. On first listen, it became an instant favourite. I can also relate to it in my own way. The ex-boyfriend mentioned in song #3 spent a lot of time publicly abusing me on social media when he tried to get me back years later and was rejected. Ironically, I noticed in his photos that he was still wearing a necklace I gave him when we were together. Therefore the lyric: you wear the same jewels, that I gave you, as you bury me made me chuckle when I heard it. Taylor is so talented at making her songs accessible and relatable to the masses. It’s hauntingly perfect.
5.) Tim McGraw
Ahhh Tim McGraw – the song that truly started it all. Taylor wrote this song in math class when she was only 15 years old. It’s about a boy she dated in high school who was going off to college. They knew their relationship was going to end, so she created this piece to immortalise their young love. When I listen to this song, I picture endless summer nights, slow dancing and the nostalgia that comes with teenage romance. It’s a beautiful, happy song devoid of any heartache. Recently, somebody online noted that in the film clip, she’s lying by a lake and her latest song is titled: The Lakes. It feels very full-circle when you think about it. I cannot express how much I adore this track.
Ugh August…you were love at first listen. I have to mention Taylor’s friend, songwriter and record producer, Jack Antonoff. When they come together, they create SUPERIOR music – more on that later. The day Folklore was released, Jack tweeted that August was his favourite collaboration with Taylor. He signed off with: August forever. You can see how much he loves it in Folklore: The Long Pond Studio Session on Disney+. It’s impossible not to picture the beach, fields full of flowers and summer dresses when this song plays. In this album, Taylor created a fictional love triangle spanning across three tracks: Cardigan (from the perspective of Betty), Betty (from the perspective of James) and August (from the perspective of ‘the other girl’ – who is never named). It talks about forbidden romance, unrequited love and fleeting passion. I could write about this song all day.
7.) White Horse
White Horse is another track #5 song on her album Fearless. I feel like a lot of people, particularly females, would be able to relate to this one. It’s about being devoted to somebody who doesn’t notice until it’s too late. Have you ever woken up from a supposed ‘fairy-tale’ only to realise cold, hard reality staring at you in the face? This song is a metaphorical bucket of cold water being dumped on its listeners. Sometimes we get swept up in the idea of a person; hoping they will be our prince on a white horse but a lot of the time we end up being let down. Taylor expresses this kind of heartbreaking disappointment so beautifully. I feel so many things when I hear it. Especially when she says: this ain’t Hollywood, this is a small town. I grew up in a small town so needless to say, teenage me was screaming!
8.) Should’ve Said No
I don’t think I’ve ever been cheated on, so I can’t say I relate to this song personally, but I love it nevertheless. It’s country but sassy and will have you saying ‘yaaaaaas’ to every lyric. It was written about a high school boyfriend who was unfaithful to Taylor. She showed the world that if you mess with her, she’ll write a soul-crushing song about it that you’ll never forget. I don’t have much to say except I love that it exists. It’s timeless.
9.) Cruel Summer
You know what’s really cruel? That this song wasn’t ever released as a single! Why? I’ll never understand that travesty. This is my first favourite track from her second newest album: Lover. It has so many layers. Firstly, Taylor is referring to the summer of 2016 when Kim Kardashian attempted to publicly assassinate her character. She received so much unwanted, critical attention which took a huge, emotional toll on her. At the same time, she was falling in love with Joe and it was quite obvious that this relationship was unlike any she had ever experienced before. He was the first partner she decided to keep private and they spent a lot of time meeting in secret. Hence the title. Taylor wanted to enjoy her summer and newfound romance but it was taken from her by the press, social-media trolls and haters.
10.) Getaway Car
Jack Antonoff strikes again! This song is superior. That is the only word I can use. If you didn’t know, this song is about Tom Hiddleston and how he was a metaphorical Getaway Car from her toxic relationship with Calvin Harris. They met at the Met Gala (hence the lyric: think about the place where you first ‘Met’ me – double meaning). Taylor wanted to leave Calvin and Tom gave her that opportunity. Unfortunately, it meant a lot more to him than her. This song was her way of apologising to him if he felt used but also that he should never have read so much into it to begin with. He was essentially a rebound. I like how she disguises this moment in her life underneath a Bonnie and Clyde theme.
11.) Never Grow Up
If you have a child, this song will hit you so hard in the feels, you won’t help but shed a tear every time you hear it. I never paid attention to it until Abigail was born and now it is so near and dear to my heart. It’s about wanting somebody to stay young, so they never lose their innocence. That takes on a whole new meaning when you become a parent and your soul aches to keep them small. Ahhh!
The more I listen to Betty, the more I’m convinced this is one of Taylor’s best songs. We know now that Joe (AKA – William Bowery) wrote it alongside her. It is from the perspective of James, who is regretful of the way he cheated on Betty and wants to win her back. The opening melody with the harmonica hearkens back to her earlier country music. I am obsessed with it. It builds up and up to a final desperate outburst from James shouting: so I showed up at your party. Will you have me, will you love me? It always makes me emotional. Some fans believed James was a female and that the relationship with Betty was of a sapphic nature. Allow me to explain. Taylor is very good friends with actress Blake Lively. Blake and Ryan Reynolds have three daughters: James, Inez (who is mentioned in this song) and Betty. Because their daughter James is a girl, they believed she was in the song as well. However, Taylor confirmed in her documentary that he is male. Not that it matters! It’s an iconic song!
13.) King Of My Heart
Before Lover was released, I referred to Francis as the king of my heart so in my world, this song is about him. In Taylor’s world, this song is about her current partner Joe. As I mentioned in Cruel Summer, she kept Joe as private as possible so their love bloomed in secret. Her lyrics refer to their relationship as a kingdom (which pops up in other songs like Hoax). It made fans so happy that she had finally met a man worthy of her; one unlike any of the others before. If the words weren’t superior enough, the production is insane! Listen to the changes in tempo and repetition of the chorus. It perfectly encompasses a life being turned upside down by an epic love.
14.) Cornelia Street
This is another track from Lover that I believe is super relatable to a lot of people. It is about an apartment that Taylor rented in New York on Cornelia Street with Joe. They made a lot of happy memories there together. She sings with great vulnerability that if her and Joe ever parted ways, she would never be able to walk past Cornelia Street again. The heartache would be too much. If you’ve ever loved and lost, you would be able to understand that there are certain places in the world that remind you of that person and to re-visit them would be painful. It’s one thing to tell your fans that you’re in love but it’s another thing entirely to express how much you hope it never ends. It’s that kind of raw honesty that makes this song one of my favourites.
15.) I Knew You Were Trouble
I’m sorry to deeply disappoint any fans reading this but I Knew You Were Trouble is the only song on the album Red that made my list. Rest assured, Red, All Too Well and State of Grace were runners-up. If you weren’t aware, this album is mainly about her relationship with Jake Gyllenhaal. It is punchy, catchy and so relatable. There’s always that one love interest/crush that we knew was trouble but went along for the ride anyway. This song proves that sometimes mistakes have to be made even if the writing was on the wall. I love it.
Back to Folklore because it really is a superior album. Take a shot every time I use the word superior in this post. I’m not even sorry! Seven is so relatable it hurts. It’s about a child that Taylor used to know, who came from an abusive household. They would play together and in those innocent moments, the kid was able to forget about their home situation. My best friend and I agree that in our past, she is Taylor and I am the unnamed child. I’ve mentioned this before but I grew up in a toxic environment. I spent a lot of time at my friend’s house, seeking refuge from my reality. It’s hard not to cry when I hear the lyrics: ‘and I’ve been meaning to tell you, I think your house is haunted. Your dad is always mad and that must be why.’
17.) How You Get The Girl
It’s the first and only track from 1989! Don’t @ me friends! How You Get The Girl was a song I listened to quite frequently before and after my husband proposed to me. Therefore, I always associate it with our engagement and happy memories vacationing in Vietnam. In reality, the majority of this album is about Harry Styles, who was one of her better boyfriends. She holds no ill will towards him. After they broke up the first time, he begged her to get back together, which inspired this song. I like how upbeat and poppy it is.
18.) Forever & Always
Are you surprised that I’m back to country Taylor? I’m not! Forever & Always is about her relationship with Joe Jonas, who broke her heart over the phone! Not cool Joe! I can relate, having been with boyfriends who used words like forever and always, only to end things the moment it got slightly challenging. Despite the less than favourable breakup, Taylor is on good terms with Joe now. In fact, in her song Invisible String, she sings: now I send their babies presents – referencing Joe and Sophie Turner’s child. She’s long since moved on.
19.) The Man
THE MAN = YES! Can I get an amen? This song from Lover perfectly illustrates what it’s like to be a woman living in a man’s world. Men are allowed to be mad, sad, players, successful business people, industrious and powerful. Women are ridiculed and shamed for such endeavours. In the film clip, Taylor actually dresses up like a man and makes fun of what it means to be born a white, privileged male. She’s not afraid to be ‘controversial’ and highlight how messed up society can be. ICONIC!
20.) So It Goes
Finally, I want to share a song that not many would expect to see on this list but here we are. Reputation is Taylor’s darkest, edgiest and sexiest album. She never meant to create it, but after everything that happened with Kanye, she scrapped all of her work and returned with this masterpiece. Look What You Made Me Do is her way of expressing that Rep wasn’t the original plan. So It Goes is clearly about Joe, with the telltale words: gold and bar. In my opinion, it’s her f#$k it song. She’s done being the ‘good girl’ that everyone expects her to be. Joe is a magician that cast a spell on her and she wants him in every way possible. All the pieces have fallen into place. If her reputation is at an all time low, she might as well do ‘bad things.’ We love edgy Taylor. I find this song to be quite empowering.
I hope you enjoyed. I’m sure you were expecting more of her well-known tracks to be on this list. In my opinion, I prefer her non-single/popular songs. Please share your lists down below! Here’s to many more years of Taylor blessing us with her talent!
Peace & Love xoxo