What’s the most annoying Taylor Swift song? Our music writers weigh in

I feel bad about choosing this.

Taylor Swift was a teenager when she co-wrote this song about an unrequited crush on a boy named Drew, and it doesn’t feel good to criticize a teenager taking a big swing and putting herself out there but still, I forge on. This would have been perfect (and scandalous) for her high school talent show, but by then Swift was a rising country star opening for the likes of Rascal Flatts and George Strait. When it peaked on the Canadian charts in the summer of 2007, I was a rookie reporter, always in my car, accompanied by this song: a saccharine, amorphous blob of young, unrequited love, with no edge or entertainment value. There was a raw honesty and a relatability there — but it wasn’t interesting. Every time she sang “Drew looks at me,” I shuddered. He seemed pretty unremarkable from her lyrics, and here she was, “wishing on a wishing star” for him. Blech. The closed captioning in the music video tells you everything you need to know: “Gentle wistful music continues.” 

I like Taylor Swift’s music. I respect her storytelling ability, her turns of phrase and her messy airing of romantic grievances. But in these early years, she hadn’t figured out how to combine those things in a way that didn’t irritate me. That was still to come. “Teardrops on My Guitar” walked so “Dear John” — her excoriation of John Mayer — could run. — Katie Daubs, Toronto Star 

In many respects, “Look What You Made Me Do” was the perfect Taylor Swift song for the moment: a booming, bass-drenched, armour-plated cyber-pop monster that firmly announced that the breezy country-pop Taylor Swift of the past was long gone and ready to claim her throne as the reigning Queen of All Media with 2017’s big-‘n’-shiny “reputation.”

Yes, songs and albums about the Agony of Fame from pop stars rich enough to buy and sell small countries can be a little tiresome, but everyone from John Lennon and David Bowie, to Radiohead and Nirvana, to Britney Spears and Justin Bieber have done it to generally respectable returns. It’s almost a rite of passage.

The trouble with “Look What You Made Me Do” isn’t even that you have to buy into the running soap opera that is Taylor Swift’s life to “get” it. That is, after all, what one signs up for when one joins Team Tay-Tay. The problem is that Swift derails a tune brimming with unexpected nastiness and graced with a seductively slippery chorus (“Ooh, look what you made me do / Look what you made me do / Look what you just made me do / Look what you just made me …”) and a smattering of entirely competent white-gal rapping with that damnable break: “I’m sorry, but the old Taylor can’t come to the phone right now. Why? Oh, ’cause she’s dead.”

It’s so unnecessary in a song that’s already made the point quite clearly, and so self-satisfied and blindly narcissistic that it doesn’t realize it’s derailing the entire thing with its painful cheesiness. It’s hard to get past. I love the song every time I hear it until that exact moment. It angers me to think about it. And I think I’ve passed the moment where I’d come to embrace it as “so bad it’s good” by now. Why ruin a perfectly good tune, Taylor? Why? Someone should have said “no.” — Ben Rayner, music writer

Anyone who knows me knows that I am a long-time, resolute Taylor hater. Her music, to my ears, ranges from bland to insufferable. I find her persona, as both a performer and a public figure, is grating, self-involved and conspicuously inauthentic. Then there’s the endless Taylor Swift news cycle — new albums! re-recorded albums! bonus tracks! Grammys! Super Bowl appearances! insubstantial political statements! — which can only be described as exhausting. Indeed, since she first emerged onto the scene some 18 (!) years ago, the spectre of Taylor Swift has loomed like global warming, quietly inescapable, inevitable. 

“Chill out, man” you might say. “No one is forcing you to listen to Taylor Swift. There are plenty of artists you listen to that we find annoying, too.” Fair enough! And yet, part of what makes Swift so insidious is the fact that you cannot truly escape her. I learned this the hard way, in 2020, with the release of “folklore,” in which the country-singer-cum-pop-star teamed up with Aaron Dessner to rebrand herself as a wispy, introspective folk artist, commencing a new era that we might describe as indie rock gentrification. This was a tough pill to swallow, given the fact that Dessner is a key member of the National, who happen to be one of my favourite bands of all time. For the next several years, I was forced to watch helplessly as Swift racked up both praise and accolades — including the Grammy for album of the year — for what to my ears sounded like a heavily diluted version of the National; a dull, sleepy mimicry stripped of the brooding angst and catharsis that makes that band so special to me. 

Eventually, I got over it (get your bag, Aaron). That is, until the National released their ninth studio album, “First Two Pages of Frankenstein,” last year. To my horror, the album contains a track titled “The Alcott,” which features — you guessed it — Taylor Swift. A boring, lethargic dud, “The Alcott” now stands out like a monstrous wart amid an otherwise stellar album, a reminder that nothing is sacred; nothing beyond the sticky fingers of all-consuming mediocrity. — Richie Assaly, Toronto Star

It might be hard to believe, but there was once a time when Taylor Swift didn’t collaborate with producer Jack Antonoff. These days, Swift and Antonoff work together constantly; his sonic fingerprints are all over her recent discography. (And hey, that’s not a bad thing.)

But, dear reader, the Antonoff era began only in 2013, when Swift agreed to feature on the soundtrack for the James Corden-starring film “One Chance.” The film’s release fell right between albums for Swift: 2012’s country-pop smash “Red” and 2014’s not-country-very-pop-even-bigger-smash “1989.”

And thus, “Sweeter Than Fiction” was born. To Swift’s credit, the track takes creative risks: a repeated bizarre-o key change between the verses and choruses makes the song memorable, if nothing else. But the lyrics snag: “Your eyes are wider than distance,” croons Swift. (Huh?) “This love is sweeter than fiction.”

Thankfully, Swift mastered the art of bubble gum pop by the time “1989” rolled around and, together with Antonoff, Max Martin, Shellback and a handful of other collaborators, she redefined the genre in 2014. It’s telling that her re-recording of “Sweeter Than Fiction” hasn’t yet made it onto streaming and was instead buried in a Target exclusive pressing of “1989 (Taylor’s Version)” last year. To quote the song, this one might have been a track to “hit the ground, hit the ground, hit the ground, oh oh.” (Seriously, what?) — Aisling Murphy, arts writer

ME! feat. Brendon Urie (2019)

I am a self-professed Taylor Swift newbie. I find her music infectiously catchy and her success awe-inspiring, but face it: She’s everywhere. I got enough of her from my siblings, cousins and friends that I didn’t need to double down myself.

But a few weeks ago, I figured I should brush up ahead of the Greatest Show on Earth paying a visit to little old Toronto. So I laced up for my jog, searched “best of Taylor Swift” on Spotify and hit shuffle. My first song, the beginning of my Taylor Swift crash course: “ME!”

Not since drummer Pete Best left the pre-success Beatles has a man been so unlucky. This song is a lifetime of pop clichés squished into three minutes and 13 seconds, a ditty that is built to live and die in the produce aisle of the grocery store. It is simplistic and generic, rehashing overwrought tropes in its lyrics and melody. That grating “me-he-he, ooh-ho-hoooo” doesn’t help.

When it was over and I could move on to the rest of Swift’s discography — the genuine modern classics like “All Too Well,” “Anti-Hero” and “You Belong With Me” — I was eternally grateful.

But the power of Taylor Swift remains. “ME!” has been stuck in my head ever since. Please send help. — Mark Colley, Toronto Star

Taylor Swift is often accused of sounding like a petulant child — often undeservingly, though sometimes she does things that don’t help her case.

“Time can heal, but this won’t. So, if you come in my way, just don’t.“ Lacklustre songwriting aside, “Bad Blood” sounds immature and petty.

The song was allegedly written about her contentious relationship with fellow pop star Katy Perry, after years of being frenemies. In an interview with Rolling Stone in 2014, Taylor candidly dished about a fellow pop star who tried to sabotage her Red Tour by hiring several dancers from under her. The internet immediately deduced that it was Perry.

And Katy legendarily responded in kind:

Here is the problem: from my experience, a feud takes one person to start and two people to continue, regardless of how vile you perceive the other person in your head. Maturity is realizing you played a part in the conflict. Take Charli XCX’s “Girl, So Confusing” remix with Lorde, which takes a much more nuanced approach to conflict between two pop stars. In comparison, “Bad Blood” comes across as cringe.

On top of that, Taylor managed to involve Kendrick Lamar in this nonsense. Why is there a remix with not one but two weak Kendrick verses?

The song’s overall existence is annoying. Maybe Katy Perry tried to sabotage Taylor’s arena tour in 2014, but the rest of us did not ask to be dragged into it. — Vernon Ayiku, music writer

I have to admit, I’m not a huge fan of Taylor Swift but, like most Gen Zs, I lived through my impressionable years watching her on TV, listening to her songs and witnessing her ever-changing music. Without a doubt, she has made some catchy tunes that evoke memories of the simpler days of being a kid.

But one Taylor Swift song that I have gotten sick of is “Shake It Off.”

It’s not that terrible of a song, its just that it’s so repetitive and has been excessively played on the radio and at almost every grocery and retail store I set foot in — trust me on this, my first job was in retail .

“Shake It Off” is a clap back at her haters and I find there is some irony to list it as an “annoying song,” but it’s a skip for me when the same lyric is repeated throughout the entirety of the last 50 seconds or so of the song, not to mention that the phrase is said around 36 times — that is excluding Swift’s countless repetition of the word “shake.”

The song’s music video owns the most YouTube views of all of Taylor’s numbers and is perhaps her most recognized track by all demographics; there’s no way of escaping “Shake It Off.”

While I agree it could be appealing to someone looking for a motivation boost, this power anthem doesn’t cut it for me with its cringeworthy lyrics and especially its breakdown segment when Swift dabbles in rapping — its just not for her. — Asma Sahebzada, Toronto Star

Christmas Must Be Something More (2008)

In Swift’s entire discography, there is only a single song that I consider a skip. 

At school, among all my friends and at every job I have ever had, I have been known as the resident Swiftie, so it may come as a surprise to some that there exists one song of hers that is absolutely not for me.

In 2007, a young one-album-old Swift released a Christmas EP, “The Taylor Swift Holiday Collection,” which featured the original song and yes, it is exactly as preachy as the title suggests. 

It asks everyone who is enjoying Christmas and looking forward to presents, mistletoe and general merriment to instead focus their attention on the true meaning of Christmas: the birth of Jesus Christ.

If I didn’t know this song was written by someone I consider the greatest songwriter of a generation, I would have imagined that it was written by the most annoying buzzkill I know.

And perhaps I could have gotten over the general preachiness and the evangelist undertones if it had not been so overt, but the chorus makes it clear this song is not about subtlety: “You’d see that today holds something special / something holy and not superficial / So here’s to the birthday boy who saved our lives.” (Ugh, I know right?)

I listened to the song for the first time in over a decade to write this and my initial assessment stands. I’m just glad that Swift pursued her more complex, nuanced music and left proselytization to the annoying people. — Abhiraj Lamba, music writer 

Before fans get all up in arms, please know that I did do a poll as a marketing research professional and it was unanimous: “ME!” is Taylor Swift’s most annoying song by a country mile.

It’s not just the self-aggrandizing lyrics whose intentions I’m sure were to constantly remind an unknown ex what they’ll be missing out on in the future over three tortuous minutes. The consensus seems to be the lead single from 2019’s “Lover” comes off as so much less empowering than its songwriter probably hoped and so much more egotistical, albeit admittedly tongue-in-cheek.

The part where she goes “Hey, kids! Spelling is fun!” is about as cringe as it gets in my music listening opinion. The video is watchable though, as the animated fanged snake at the start is pretty cool, and the French speaker in me does get a chuckle seeing Mademoiselle Swift argue in the language of love.

There’s probably a good reason why it’s only been played once on the Eras Tour (last November in Rio de Janeiro, Brazil) and not because Panic! at the Disco has never opened for Taylor so that Urie could duet with her later. — Gilles LeBlanc, music writer