The Essentials: Best 15 Taylor Swift Songs [Pop Girl Week]

Coming off of undeniably the biggest and most memorable era delivered by a pop artist, Taylor Swift was known as quite the reigning female of the music industry. Starting off as a country star who’s found mainstream success, she pulls a smooth Shania Twain as she transitions into full-on pop stardom after experimentations in two of her previous albums, earning 4 #1s and 20 T10s on the Billboard 100 along the way, and is the only artist to have had three million-opening first week sales with three of her albums. Critically acclaimed, she’s the first female artist to own two Album Of The Year awards at the GRAMMYs (Adele did the same a year after), and never failed to fall out of the news with her frequent headline-making moves – writing her open letter to Apple Music, slamming Kanye West for calling her a bitch, getting slammed back for blatant lying, stripping her music from Spotify, making a song wvith a “diss” music video all about Katy Perry, putting her music back on Spotify when Katy releases her album… and that’s not even counting her headlines with her 2 boyfriends. All that gossip aside, Taylor does have an incredibly solid catalogue, that can now be streamed at ease. So below are 15 absolute essentials from Taylor Swift, singles and non-singles included.

Fearless – Fearless (2008)

The first track and the title track of Taylor’s sophomore album that launched her to global stardom, “Fearless” is amongst one of Taylor’s best country offerings. She reveals that this track is actually about a “best first date she haven’t had”, the then 19-year-old singer wrote, and how her prince charming would bring comfort in herself, and anything is possible when he’s around. “I don’t know why but with you I’d dance in a storm in my best dress,” as Taylor sings about the feeling of courage and invincibility she feels falling in love with a person, she plants her voice into your head with its catchy melodies and instrumentation – her incredible forte since 2006.

You Belong With Me – Fearless (2008)

As Taylor’s second worldwide hit after “Love Story”, “You Belong With Me” became the anthem of every teenage girl who has a secret crush that they can’t reach. Funnily enough, the concept and story of the song was all in Taylor’s imagination in the first place, as the song was written in sympathy of a male friend of hers who’s been yelled at by his girlfriend, and is trying to make up on the phone. The classic girl-next-door narrative with the most relatable lines (“Cause she doesn’t get your humour like I do”) brought the song to #2 on the US Billboard 100, a Song Of The Year nomination at the GRAMMYs… and Best Female Video at the VMAs which we absolutely don’t need to get further into.

State Of Grace – Red (2012)

The openers of Taylor’s albums are always spot-on… except “Welcome To New York”, but the point is that “State Of Grace” is one hell of a beginning to Taylor’s blockbuster 2012 album. As her first step of transitioning from country to pop fields, Taylor takes a detour in “Red” to more pop-rock fields, and this track is a clear show of the experimentation of genres. With loud and lively drums and snares, Taylor details the surprises, highs and lows of relationships, and a blink of an eye leads to lives changed (“And I never saw you coming, and I’ll never be the same”). Taylor mentions in one interview that “State Of Grace” can be both the introduction and the conclusion of “Red” – Love is a road that goes both ways, and every intersection can mean everything.

read our best to worst songs list on ariana grande’s “my everything” here

Holy Ground – Red (2012)

Giving vibes similar to “State Of Grace”, “Holy Ground” is another energetic pop-rock anthem where ongoing thumps in the drum from Jeff Bhasker take the lead. An optimistic, towering song that never stops building, documenting another set of memories of a relationship that’s finally appreciated by Taylor after a good amount of time. “We blocked the noise with the sound of ‘I need you’,” she recalls the brilliant times in New York when everything was good. This is a classic example that it’s not always about heartbreak with Taylor – sometimes there are guys that treat her well.

Haunted – Speak Now (2010)

Opening with a huge string section with electric guitars, “Haunted” is dramatic from the beginning. Documenting a break of a relationship that will never escape Taylor’s mind, she sings with desperation questioning the reason of her lover’s departure, and with the biggest vocal intensity possibly in her discography so far. The use of big orchestration and the blatant display of emotion is one distinctive moment in Taylor’s music, as this song lives in the core of the fanbase even to this day.

Out Of The Woods – 1989 (2014)

And so we arrive in 2014 at Taylor’s biggest break, her official arrival into the world of pop. “Out Of The Woods” was the second song released to the public prior to the album, and the sixth overall single released. At first listen it may all sound very repetitive, which isn’t a surprise considering the chorus is the same line repeated over and over, but upon further listening, the synth-pop song is one of the smartest and well-produced songs on the album. Co-produced with Jack Antonoff (Bleachers and fun.) who’s also provided background vocals, the song is a great fusion of modern effects and 80s elements (oscillating whooshes in the verses for example), something Taylor went for in the era but didn’t quite hit the spot. In the final chorus, Jack and Taylor gives it all they’ve got, throwing in stacked drums, bell-like synths and glorious background vocals all at once, concluding a true highlight from the record.

All Too Well – Red (2012)

“All Too Well” is a nostalgic ballad, where Taylor is found recalling her memories of a relationship for the books, and telling them in a 5-minute emotional rollercoaster. Picked as the hardest song for Taylor to write, with over 10 minutes of material that was only cut to 5 for album purposes, the lyrics are showered with emotion and the most heart-wrenching lyrics out of Taylor’s songbook. The instrumental break is particularly so emotional as it bridges the bittersweet recall of happy memories, to some real in-depth feelings (“And you call me again just to break me like a promise, so casually cruel in the name of being honest”). And the song returns to calmness as Taylor comes out of her memory, but the imperfect ending of the song seems to just imply that the feelings still remain.

Enchanted – Speak Now (2010)

It’s not a sweeping statement calling this one the absolute fan favourite out of Taylor’s five records. The song was written after Taylor’s meet-up with Owl City’s Adam Young, to which she was “wonderstruck” about, and wrote a song for. The use of the word “wonderstruck” was intentional, as she used it from one of his emails, knowing it’ll be a secret code for him. Both melodically and lyrically, the song sounds like an absolute fairytale, as the buildup of crescendo leads to a soaring, magical chorus with the hopeful innocence that Taylor has. What makes this even more sweet is Adam’s response back to Taylor with a cover of the song, but of course doesn’t nearly reach the brilliance of the original.