Celebrating Taylor Swift’s 27th Birthday With 27 of Her Must Hear Songs

I wouldn’t think it would be wrong to assume just about everyone on the planet has heard of Taylor Swift. 27 years ago, December 13th 1989, an icon was born. Since then, Taylor Swift has managed to take over the music industry for 10 years, crossing over from country to pop and excelling in each genre. This multi Grammy award winning artist has released over 3o singles and managed to top the charts with each and every evolving album. For some people, the singles are all they have heard of Taylor Swift, all they have to base their opinion of her on. As a Taylor Swift mega fan, I find this unfortunate since I know her discography is full of a multitude of fantastic songs. This year Taylor took a break and decided not to release an album in her usual every two years fashion leaving me her entire discography to binge in the meantime while I wait for the impending release of TS6. To celebrate her 27 years I decided to show you 27 of these deep cuts that I feel everyone should hear to truly appreciate the incredible musical talent that is Taylor Swift. So listen along to my YouTube playlist and enjoy some songs that may be your favorites or that you have never heard before.

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Taylor Swift (2006)

1. Picture to Burn

No one gets more in touch with their true feelings than Taylor. Ever had someone in your life that you just wanted to erase? Then this song is for you. Taylor explores her angry side as she sings about getting revenge on a guy and embracing her inner Eliza Hamilton to burn his memory. Can you believe he didn’t let Taylor drive his pick up truck? Wonder where he is now. This track on her first album shows you that Taylor Swift is someone you never want to cross while also letting you embrace your inner woman scored.

2. Should’ve Said No

By far one of my favorite songs, and not only because she sang it with the Jonas Brothers. Should’ve Said No related to a point in my life back in high school and since then I’ve had a soft spot for this song. If you’ve ever been cheated on and need a song to get you through it, this is the one! It’s crazy to think this song was on her first ever album! Should’ve Said No tells the story of the aftermath of infidelity. Taylor taps into her emotions to tell you just why she won’t forgive and how he badly messed up the situation. It’s a great empowerment track and one of her best!

3. Stay Beautiful

This song is the definition of adorable as Taylor explores all the reasons why she is infatuated with this guy from his smile, to his eyes. Taylor describes that crushing on someone feeling with lines like “It’s hard to make a conversation when he’s taking my breath away”. Whether you’re crushing on a new guy at work or a new guy in class, this song will have you smiling and thinking about that special someone.

4. I Heart ?

This might be one that not many of you have heard so I’m excited to shed some light on it! This song never made any album which is such a shame because it is so good! This song is about dealing with a break up and proving that no guy should ever let you feel bad about yourself. You may feel crappy at the time but once you pick yourself back up you won’t ever remember that lame guy.

5. I’d Lie

This song makes it on my top ten. It’s about that moment when you’re head over heels for someone but you can’t admit to yourself just how much you love them. You know everything about them and you know you have those feelings but you can’t let anyone know. The line that hits home the most is “First thought when I wake up is my god he’s beautiful, so I put on my make up, and pray for a miracle” I used to listen to this song all the time in high school. Its almost like she wrote the soundtrack to my life. Give this song a listen and let me know what you think!

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Fearless (2008)

6. Tell Me Why

This song is about an abusive relationship and wondering why this is happening to you. Taylor describes how he loves her but also wants to bring her down and just doesn’t understand. I love the guitar vibe of this song and its so fun to sing along to and really get into. Not sure who ever put down Taylor Swift’s dreams so that he was the only thing on her mind, but it looks like she got the better end of the deal.

7. The Way I Loved You

This song is about moving on with someone else who is perfect on paper but just doesn’t give you the same feelings of your ex, even if you fought and had some turbulence. I love the imagery in this song and it stood out to me the most when I think back to when I saw the Fearless Tour. Its a great edition to the Fearless and one that I consider to be underrated.

8. Forever and Always

If you know me you will know EXACTLY, why I love this song. Two words: Joe Jonas. This song is about Taylor’s short lived romance with Joe and reflecting on the promises he made her. If anyone was around in 2008 to see all the drama between the Jaylor breakup, those were the days! Taylor gave such a good performance for Forever and Always both on tour on and on tv. Long Live the Joe and Taylor petty romance.

9. Jump Then Fall

This track made it on the second release of Fearless on the Platinum Edition. I was lucky enough to see her perform it as an encore number on the Fearless Tour clad in a custom made Patriots jersey. This song is another one for the adorable category as she describes the little traits she loves about him like his voice in the morning, his laugh. It’s about falling head over heels in love for someone, just like I did for this song.

10. Other Side of the Door

This bonus track is about that sinking feeling you have when you shut someone out and all you want is for them to chase after you. You know in the moment you need to leave but you also do it as a way to see if they will fight for you. Its a beautiful story and can relate to any type of relationship where you need that reassurance. Like most stories, the best part in the ending where she finds the person she wants most in on the other side of the door.

11. I’m Only Me When I’m With You

Grab your bestie and blast this one celebrating all the fun parts of friendship and being thankful for each other. Sometimes you just need to let your best friend know just how much they mean to you. Also not on an album, I picked this song because it sings about a different type of love as opposed to relationships. One of the best parts about this song is the video where you see Taylor hanging out with her original squad, Abigail and her friends on tour. Have a listen!

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Speak Now (2010)

12. Story of Us

This is a single unlike most on this list, but it was short lived. This song is such a bop! It has great vocal points wondering how Taylor ever manages to catch her breath. Her lung capacity is astounding! This song is about going to an event and realizing in the past that you would have sit with them but now you are doing everything you can to avoid them. It also leaves you with the dying desire to know if they miss you just as much as you are missing them. Its a fun song and one of my favorites on this album.

13. Sparks Fly

This is my ultimate Taylor Swift song and I feel that people don’t love it as much as I do so I threw it on this list to bring attention to it and change all of your minds! This song is the best! Its the definition of Taylor Swift with its beautiful imagery and metaphors. My favorite line is “I’m captivated by you baby like a firework show” and its usually the part when Taylor launches fireworks into the stadium on tour.I’m obsessed with this song and I couldn’t make this list without including it.

14. Haunted 

I feel Haunted is underrated, but its also my best friends favorite Taylor song so I have a strong liking towards it. Haunted is so different from anything Taylor has done in that it has a distinct sound and an eerie vibe. The live performance of this song is absolutely fantastic and acrobatic. A standout on the Speak Now tour! The song itself is about wanting to move on but being haunted by the past. Truly a great one.

15. Last Kiss

You wouldn’t think I would point out the first Jaylor song and not mention the second! This song is beautifully created. A 27 second introduction to commemorated the infamous 27 second phone call in which Joe ended their relationship. The specific details about their relationship like when she went to see him on tour in July, and the heart breaking thought of her wanting to check up on him and spending nights in the familiarity of her clothes. The concept is that she never knew when they kissed it would be the last. Its a beautiful ballad and a top track on Speak Now

16. Superman

This song is part of the Target bonus tracks on the special Speak Now edition. This song is a cutesy play on the idea of Superman and being proud of your man as he does what he does best. Its about letting him go off to do what he wants and being there for him when he comes back. Due to the timing I believe this song is about Joe Jonas and how he would go on tour and then come back to Taylor. Its a fun song that the average listener would not have heard so hopefully some of you will discover it for the first time and love it as much as I do.

17. Ours

File this one in the adorable category, especially once you see the video. This song is about people’s opinions on your relationship and brushing it off. The song is about embracing the love you have and not caring what others think. Just like she says “people throw rocks at things that shine but they can’t take whats ours.” Taylor explains that the bond they share is stronger than what anyone else has to say about it. Another Target bonus track and another must hear song.

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Red (2012)

18. State of Grace

This song kicked off the Red tour and I feel like it was slept on. Its a great kick off to the album if you’ve never listened to Red you have seriously missed out. Taylor sings about how this love might have its trials and tribulations but that’s what makes it special and worth fighting for. I have such fond memories of seeing this on the Red tour and for me it defines the Red era.

19. Holy Ground

This. song. is. fire. The beat is so fast that you can’t help but get excited and bounce along. Its about reflecting back on a relationship to when everything was perfect and you stood on holy ground. I love the lyrics in this song “Tonight I’m gonna dance for all that we’ve been through but I don’t want to dance, if I’m not dancing with you” I can’t quite describe why I love this song but it hurts that not everyone has heard it so do me a favor, give it a listen, and correct that for me 🙂

20. All Too Well

This is lyrically Taylor Swift’s best song, and quite possibly going to be the best 5:29 minutes of your life. I’m not even being dramatic this song hits home in so many ways. I have spent so many days weeping over this song about a relationship I never even had! Its a beautiful story about thinking back on your relationship and all that you went through together. This song has some hard hitting lyrics like “I’d like to be my old self again but I’m still trying to find it” and “I might be okay, but I’m not fine at all” and of course who could ever get over the climax of the song “you call me up again just to break me like a promise, so casual and cruel in the name of being honest” I could honestly go on and on about this song but I’m just going to stop now and let you listen.

21. Starlight

“Oh my, what a wonderful tune it was the best night ever won’t forget how we moved” This lyric describes me every time I listen to this song. Taylor travels back in time and creates a story about the Kennedys meeting back in the day. Inspired by the short lived relationship with Connor Kennedy, this song has an old school feel and its impossible to not dance to. One of the many great songs on Red.

22. The Moment I Knew

This is quite possibly Taylor’s most heart wrenching song. After Jake Gyllenhaal told Taylor that he would come to her birthday, the dumb bastard had the audacity to not show up, leaving Taylor to be upset in front of all her friends on her birthday. She recounts the moment she knew it was over, when he didn’t show. The power ballad feel adds to the overall emotion this song brings, making you want to slap Jake for ever making Taylor have to endure this pain. This song can be found as a bonus track on Red and in my opinion, is one of the best.

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1989 (2014)

23. I Wish You Would

Time to venture into my favorite territory, Haylor! For those that don’t know Haylor refers to the relationship between Harry Styles and Taylor, the inspiration behind almost every song on 1989. I lived and still live for this relationship, making I Wish You Would one of the songs that I believe everyone must hear. This song is upbeat and fun and such a great part of the album. On this track Taylor talks about the things that remind her of Harry and how she wishes more than anything he would come back, that she wished he knew how much she wanted him back despite the hiccups they may have had. I have faith he will come back one day but for now I’ll just be standing behind Taylor wishing he would. (Due to copyright 1989 songs are not on youtube, I have posted similar videos of the songs)

24. I Know Places

Another Haylor classic about how the media and the fans destroyed their relationship. Taylor described how she wanted to just run away from it and go to a place where they could be in love in peace. She creates a metaphor that they were being hunted and trapped but she knew where to go to escape it all. This song rips my heart out as she sings “And I know for me its always you” “I know for you its always me” They were so in love its such a shame so many outside factors ruined it.

25. Wonderland

The best bonus track on 1989 turning Haylor into the story of Alice and Wonderland as they fall down the rabbit hole and both go mad as they get lost in Wonderland. I love this song for that concept and for how it displays Taylor’s creativity. Some people have yet to hear the deluxe album and this song should be your first stop. I promise you will fall down the rabbit hole and be madly in love with this track.

26. Clean

Many songs are about breakups, but not many are about finding yourself and cleaning yourself from the past. This song just does that, its that moment in which Taylor was able to move on from the relationship and find herself as described in the songs secret message. This song is important because it allows you to learn that the most important person is yourself and once you take care of yourself you can move on. It’s truly beautiful.

27. You Are In Love

Last but not least, this song is painfully adorable. Not written about any of Taylor’s personal relationships, this song is about that feeling of being in love and recognizing the changes in your life once you fall. How you can feel it all around you. The best part is when he “pauses and says, youre my best friend” Ugh it kills me every time! If you haven’t listened to this track please treat yourself!

There you have it! 27 songs for 27 years of Taylor’s life! Please let me know what songs are your favorites, what songs you never heard before, and any songs of hers that you believe deserve a spot on the list! Just comment below or tweet me @shelleyann1817! Also feel free to share the wealth and let everyone hear these must hear songs. HAPPY BIRTHDAY TAYLOR!



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