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I Listened to Every Taylor Swift Album (On a Bet)

Taylor Swift performing at Madison Square Garden, 2019.
Credit: Shutterstock/Brian Friedman

The day was February 11, 2024. Super Bowl day. For some stupid reason, I made a bet that if the Chiefs won the game, I would listen to the entire studio discography of one of music’s biggest stars… Taylor Swift. Guess who won.

Here’s a little context about me – I am not a pop guy. I’m much more inclined to listen to Ghost than Olivia Rodrigo. So when I say this was stepping out of my comfort zone… that’s an understatement. 

Before I began my journey, I set a few ground rules to keep this from taking too long: I would only be listening to the standard version of each album, meaning no bonus tracks. I also left out Swift’s live releases, since they didn’t fit as well into her catalog. I did include the re-recorded versions of her catalog, but I don’t have enough to say about them since, let’s be real, they’re basically just the same albums again.

With all that out of the way, sit back, relax, and enjoy my descent into madness as I accidentally became a Swifty.

Taylor Swift (2006)

I wish I could say I really hated this debut, but it’s honestly kind of nothing. It’s a standard generic mid-2000s country-pop album. There’s nothing special about it.

What’s mind-boggling about this is that almost every song sounds identical. There’s nothing different between big hits like “Teardrops on My Guitar” and a deep cut like “Stay Beautiful.” 

To be completely honest, there’s nothing about this unassuming debut that points to the monstrous heights Taylor Swift would eventually scale. It’s just a simple and sweet country album, but it’s far from what I would have expected.

Fearless (2008)

I have split feelings on Fearless. The songwriting is just as cloying and frustrating as it was on the debut, but this one lacks sincerity and honesty. It no longer feels genuine, instead being replaced by factory driven corporate pop-country. 

Then there’s “Fifteen,” a song so heinous and annoying that it makes Olivia Rodrigo’s self-pity complaining sound rational. I never thought I would favorably compare “Drivers License” to ANYTHING, yet here we are. 

With that said… this album does soar high. “You Belong With Me” is a classic for a reason. “Love Story” hits too. But the rest of the album is a slog to get through, with too many ballads that sound identical.

Speak Now (2010)

From the first second of the album, it’s clear that something is different. The vocals aren’t amateurish and annoying anymore, and while they still aren’t much to write home about, they have a ton of confidence. The lyrics and music are a vast improvement as well. Sure, songs like “Mean” slip through the cracks, but tracks like “Back to December” more than make up for the duds. 

The one-two punch of “Never Grow Up” and “Enchanted” was also extremely powerful. There’s something about the overwrought sentimentality that really clicked. It is completely ruined by “Better Than Revenge” coming immediately after. 

Red (2012)

Look, I’m a classic rock guy, so I appreciate the “harder” edge some of the tracks have here. Sure, the lyrics are still not great for the most part, but the energy is usually high enough to keep my interest. And then we get to the second half. 

Everything after the goofy “Stay Stay Stay” is an absolute slog. Every song sounds exactly the same. Why did it need to be over an hour? Why did it need 16 songs? Why the duets?

If this were 3 or 4 songs shorter, I would favor Red a lot more. But it’s just too long to make the few highlights worth it. 

1989 (2014)

I had earlier dismissed the concept of her “eras,” but I was clearly wrong since she’s changed a lot since that debut. What’s interesting about the poppiest Taylor album so far is that the biggest songs (“Shake It Off,” for example) are easily the worst ones. Maybe it’s just that they’ve all been played into oblivion, but the lesser cuts are superior. This album also has shockingly good production, with a clean and polished sound that is very pleasing to the ear. 

While this album is perhaps Taylor’s most impressive vocally thus far, it also exposes her as… not that good of a singer. She’s regularly riffing and reaching for high notes, exposing her singing voice’s overall lack of character.

Reputation (2017)

In an article titled “What Is Hell,” author R. C. Sproul posits that Hell is  “a suffering torment from which there is no escape and no relief.” Reputation is the sixth studio album by Taylor Swift. 

The issue here is that Taylor tries to make herself look vengeful, but nothing about her music before this has given ANY indication of this shift in persona. She just doesn’t have the range or credibility.

“Look What You Made Me Do” is not only Taylor’s worst song thus far, but it’s one of the worst songs I have ever heard in my entire life. Terrible lyrics, ear-bleeding production, that cringe-worthy line about the old Taylor… what even happened here?

I genuinely haven’t had this negative of a reaction to an album ever. Ship it to a landfill, then set the landfill on fire.

Lover (2019)

Despite my initial doubts, Taylor Swift has proven herself to be capable of evolution. Every one of her albums to this point has built off of the previous one and driven her in a different direction. Lover, however, is a giant step back. It’s almost like she knew Reputation was awful and decided to retreat back to what made 1989 work… but forgot to make it good.

While the production is much safer and less grating than Reputation, the songs are just as bad. I couldn’t even finish “Soon You’ll Get Better.” “Me” is condescending and annoying as hell. “You Need To Call Down” pretends to be activism but truly only comes across as a worse version of “Shake It Off.” 

Lover is sickeningly sugary, painful on the ears, and ultimately deserves to be forgotten – except “Cruel Summer.,” which is completely innocent.

Folklore (2020)

Rather than continue in the overproduced pop sound she’d been dabbling in, Swift strips back the layers, giving barebones musical structures to allow her lyrics to rise to the surface. While previously that may have been an issue, here the lyrics are easily the best of her career.

Taylor seems to be emulating Phoebe Bridgers here, both music-wise and lyric-wise. Similarly, there’s not a single bad song here. My only regret about Folklore is that she hadn’t experimented with this sound earlier because she does it expertly. She sounds at home here. I hope she continues with this type of music for a bit.

Evermore (2020)

Well, I got my wish. Evermore is basically just a worse version of Folklore – the same woodsy atmosphere but with much weaker songwriting. It does have guest appearances from Bon Iver and The National though, so points for them. 

Much like Folklore, there’s nothing bad really on here (well, save for “Closure.” Why was she doing a British accent for half the song?), but there isn’t much that stands out. She doesn’t throw many hooks here, and while that does show range as a writer, it makes for an uninspiring and dull listen. 

This is honestly just a boring record. There’s nothing to criticize but also nothing to praise. It would’ve been hard to follow up Folklore, for sure, but even so, this is disappointing. 

Midnights (2022)

Swift’s last album of original material (for now) is reminiscent in many ways of Evermore and Folklore, in that all the songs pretty much sound the same. The difference, however, is that all the songs on Folklore were good, and here they’re… not.

“Antihero” is one of the worst songs in Swift’s entire catalog. From its cringeworthy lyrics that don’t even make sense, to Taylor’s ear-bleeding singing, to the forgettable melody and limp production, it’s a song that does nothing at all right.  

Something else about this album – Taylor really steps up the cursing. Normally, I wouldn’t care, but Taylor sounds like a little kid learning to swear for the first time. 

It’s one of her weakest outings as a writer and easily her worst album as a vocalist. Never before has she seemed to run out of breath on multiple songs. I’m either hearing things or her voice is shot.

The Grand Finale

24 days. Over 34k minutes. Over 2 million seconds. 3 weeks and 3 days. That’s how long I was stuck in Taylorville. 

What an experience this was. I got to reevaluate songs that our generation has been brought up on, as well as discover gems in a catalog that, frankly, I was predisposed to hate. 

Now sure, Taylor Swift has put out a LOT of garbage. But with that said… when she hits, she REALLY hits, and for that alone, I can recommend her as a worthwhile artist. 

This was a super fun challenge that helped me discover some good songs and albums I wouldn’t have dared touch before this. See you all again on April 19th! (Seriously though, what even are some of those track names? “Fortnite?” Come on.)

If you’re interested in hearing more about one of Taylor’s best albums, you can read this review!

Written By

Danny Krastek is an award winning writer, director, on air DJ and film critic attending college at Montclair State University.

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