The End of an Era: Ranking Taylor Swift's 13 Best Songs Ever

After Swift announced the big news that she is moving to Republic Records and Universal Music Group after 12 years with Big Machine Records

By Tierney Bricker Nov 19, 2018 8:28 PMTags

Taylor Swift officially has a new home.

The 28-year-old superstar just shook up the music industry in a major way with her announcement on Monday that she will be leaving Big Machine Label Group 12 years after releasing her debut album, signing a new deal with Republic Records and Universal Music Group. And she did it in a big way, claiming complete ownership over her entire catalog of songs moving forward.  

"I'm ecstatic to announce that my musical home will be Republic Records and Universal Music Group. Over the years, Sir Lucian Grainge and Monte Lipman have been such incredible partners. It's so thrilling to me that they, and the UMG team, will be my label family moving forward," the 10-time Grammy winner announced via her Instagram. "It's also incredibly exciting to know that I'll own all of my master recordings that I make from my own."

Taylor Swift's 13 Best Songs Ever
Emma McIntyre/TAS18/Getty Images for TAS

Since releasing her self-titled debut album at 16 years old, Swift has put out six albums, selling more than 40 million albums and becoming one of the best-selling music artists of all time. Oh, and let's not forget that she writes all of her own songs, with many reading like her own personal journey entries which have become the soundtrack to many of her fans' lives. 

"I'm extremely grateful to get to do what I love, especially with the people I've been fortunate enough to work with," she wrote. "The best thing I've been lucky enough to receive is the dedication, trust and loyalty of the fans who have cared about the words and melodies I've written. my biggest goal moving forward is to make you proud. I'm so excited. I can't wait to show you what I'm making next."

Of course, Swift's major move marks the beginning of a new era for her as an artist and a businesswoman. To properly look back on and celebrate her historic 12 years at Big Machine, we ranked her best 13 songs ever, and trust us when we say it was a long and difficult journey,but we made it "Out of the Woods"...even if that didn't make the list.

13. "Safe & Sound"

OK, so technically this wasn't on one of her albums, but whatever! Our list, our rules, and "Safe & Sound," the duet with The Civil Wars off of The Hunger Games soundtrack is just the perfect example of Swift's ability to adapt to any other artists' style (something she does with all of her duets, by the way!) and proof of how talented a songwriter she really is.

12. "The Other Side of the Door"

Swift always makes buying the platinum or deluxe editions of her albums worth it, and "The Other Side of the Door," an additional track off of Fearless' platinum edition, is one of the best.

11. "Should've Said No"

"Should've Said No" hails from her 2006 debut album, and 12 years later, it more than stands the test of time. It's vengeful without being petty, calling out a cheating ex...and is a particularly great one-two punch when paired  with "Picture to Burn." Just sayin'. 

10. "Our Song"

Yep, this is still the cutest little love song, and shows off one of Swift's best songwriting skills: telling an entire story in a single sentence: "When we're on the phone, and he talks real slow 'cause it's late and his mama don't know."

9. "Mine"

The lead single off of 2010's Speak Now is rare for Swift in that it's one of the best songs off the album, not always the case for the lead singles (See: "Look What You Made Me Do" and "We Are Never, Ever getting Back Together," which are both solid pop songs, but not the best pop songs on their respective albums, don't @ us!). Oh, and "Mine" has this absolutely killer line, one of Swift's best ever: "You made a rebel of a careless man's careful daughter."  

8. "Dear John"

The message was clear: do not f—k with Swift's heart or you will get publicly called out and shamed via . Intended target John Mayer later said he felt "humiliated" by "Dear John," thanks to lines like, "Don't you think 19 is too young to be played by your dark twisted games, when I loved you so?" Basically, she called him a f—kboy before we had the term at the ready to use.  

"It made me feel terrible," Mayer told Rolling Stone. "Because I didn't deserve it. I'm pretty good at taking accountability now, and I never did anything to deserve that. It was a really lousy thing for her to do." He also called it "cheap songwriting."

Swift's response? "How presumptuous!"  (We're not worthy!)

7. "Fifteen"

Listening to "Fifteen" now sort of feels like going home for the holidays and discovering your old diaries. You are cringing reading it, but you can't help but have a huge smile on your face while doing so. This ballad about experiencing high school heartbreak with her BFF Abigail Anderson is delightfully over the top in the way you can only be as a freshman, experiencing these feelings for the first time. It's OG Swift and respect must be paid, especially since these two had the last laugh.

6. "Delicate"

It's not often we get to watch an artist mature and become a grown-ass woman right in front of our eyes with the class that Swift has, and "Delicate" is the perfect embodiment of how her views of sex and dating has evolved. Also, the references to just how famous she is and aware of what the public and media think of h er—"My reputation's never been worse"—fared far better on this track than those that shall not be named.

5. "Wildest Dreams"

Deliciously dreamy, "Wildest Dreams" is Swift at her most  achingly romantic and it's irresistible. Also, Instagram caption galore! Don't lie, you've totally used, "Say you'll remember me, standing in a nice dress, staring at the sunset, babe."

4. "New Year's Day"

Oh gosh, if this unabashedly millennial love song ("Candle wax and Polaroids on the hardwood floor…") isn't the most gorgeous song on Swift's latest album. While the rest of Reputation was all-pop, "New Year's Day" ended the album on such a sweet and touching note. It's no wonder it made Jimmy Fallon cry when Swift came on The Tonight Show and performed it.

3. "Style"

Fact: Trouble for Taylor's love life translates to happiness for our ears. One of the many break-up bops her romance with One Direction's Harry Styles gifted us with. ("I Knew You Were Trouble" was this close to making the list!) "Haylor" may have gone out of style, but "Style" is a Swift jam for the ages. 

2. "Blank Space"

Oh, you think Tay has had too many boyfriends? And that she writes too many songs about the relationships? Well, "Blank Space" is her answer for you. "Got a long list of ex-lovers / They'll tell you I'm insane / But I've got a blank space, baby / And I'll write your name."


1. "All Too Well"

All nostalgic, all bittersweet, this track off of Red is peak Taylor Swift. With sly and sometimes not-so-subtle references (The scarf! Plaid shirts!), it's a breakup song for a generation that paints the perfect picture of a girl loving a boy more than he loves her; you can actually see the love story playing out in your head, dancing in the refrigerator light and all. We are still convinced Jake Gyllehnaal should have these lyrics tattooed on his body, that's how much of an honor it is to have this song written about you!

Sample lyric to properly pay respect to "All Too Well":
"Hey, you call me up again just to break me like a promise, so casually cruel in the name of being honest."

(E! and Universal Music Group are both members of the NBCUniversal family.)