The Swiftening, Part 1: Taylor Swift (2006)

(EDITOR’S NOTE: Earlier this week, I reviewed the new album from Taylor Swift. My friend, the perfect and hilarious Jordan Holmes, responded as such:

From that tweet came great discussion. From that discussion came the idea for Jordan to review Swift’s entire discography. Here is part one, a look at the 2006 self-titled debut.)

Until today (when I’m typing this today, not when you’re reading this today), I have never before heard a Taylor Swift song. Despite her having released culturally dominant albums consistently for the past 14 years, I have avoided every one of them. It was easy at first, her first album was a crossover teen pop hit and stuff but back then it was still housed in a music world I rarely came in contact with.

I began my music collection when I was 14. My computer had a cd burner and the internet accidentally made all music free (whoops!), instead of listening to the radio and watching TRL, I scoured torrent sites for everything that piqued my interest. An example would be what happened after I heard The Roots “Seed 2.0” for the first time. I downloaded the album. Then I read interviews ?uestlove gave where I learned about Cody Chesnutt and the Soulquarians and downloaded all of their albums, too. Then I read interviews with _____ and learned about ____ and downloaded all of… and so on. Now I have just so much god damn music, from every era, from every genre and I always choose what to listen to.

And none of it was Taylor Swift. 

Because I only ever listen to my own music, and because I’m a grinchy shut-in, I can avoid anything if I want to avoid it. She, I wanted to avoid.

My little sister listened to Taylor in the beginning, I remember her trying to play that shit in my car and me not having any of it. I hadn’t listened to it, but I knew it was shit because I was 18 and she was my little sister and that’s the only explanation that would hold up under a lie detector test. It was easy to write off a teen country singer.

Then, when the whole Kanye thing happened in ‘09, I was confronted with a musical genius doing something hilarious and legendary – outshining Keith Moon by a longshot – only everybody felt bad because it came at the expense of a teen country singer and, like… I get it… it was a real dick thing to do and it was wrong and Swift didn’t deserve to have her moment taken away from her like that. So I did the brave thing and avoided caring about it because I liked Kanye more and I never regretted that decision for a moment.

Now here we are in 2020 and no one expects you to defend Kanye’s behavior anymore if you like his music; he’s gone so far off the rails you can’t help but separate the art from the artist. Shit, he’s a fucking Kardashian now; we’re a long ways away from Chappelle’s Block Party. 

The time has come for me to listen to Taylor Swift. But I’m only going to do it for content! Enough preamble.

Taylor Swift’s first album was released when she was 17 and was titled Taylor Swift so I will be grading on a curve. I’m a 33 year old man and it would be very sad for me to shit on lyrics that appeal to the hearts of teenage girls all over the world even though they are terrible lyrics and anyone who says otherwise is wrong. 

So I won’t be shitting on her lyrics, I’m above that kind of thing. 


The first song on this album is “Tim McGraw” (I’m just now realizing how hard this is going to be because I almost wrote, “…and the lyrics are shit”). “Tim McGraw” is emblematic of what made the album successful and also of what makes it so terrible. Listening now it’s impossible not to see her starpower. I can imagine myself a mustacheod studio exec wearing expensive furs, a bluetooth ear piece and a phone holster, listening to this demo for the first time and thinking, “I am going to make so much fucking money.”

Her voice is right. She can add a light breathy quality while maintaining perfect timbre, which is fucking key. (Stray thought, is it even legal to call a song “Tim McGraw”? Does he get royalties?) If you can make your voice pout, whisper, and still wail, you’re going to be good at country music. 

They made the smart move, as with all of her songs, to make her vocal track prominent and they were rewarded with a billion dollars. She’s a true star.

But this gets me back to my mission statement, this music is bad. It is bad for you. The guitar track is shit. There’s a floating ukulele that comes and goes like all-protein diets. They should be criminally prosecuted for forcing a violinist to play that simple garbage. The drummer plays like a Christian. They fade out on an awful strum. THE BASS PLAYS ONE NOTE. MAYBE! 

Worst, though, when they first break into the chorus, after the little swelling crescendo and that background guy shows up to sing, “When hyew think Tim McGraw” I cannot stop laughing. How dare someone make me listen to a song that features Tim fucking McGraw as a plot point. Get the fuck out of here. 

And how dare any of you listen to it!


Track 2 is “Picture to Burn” and it could easily be dismissed as Avril Lavigne with bluegrass instrumentation, a ra-ra message of vague nihilism, and the banjo player from an anthropomorphized robot bear jug band. So I will.

(Oh my god, am I going to do every track? I’m listening to the deluxe edition, this thing is 15 tracks and two of them are the same god damn song.)


“Teardrops on my Guitar” is track 3 and 15. Track 3 is the country version and track 15 is the pop version and yes, they’re more reminiscent of one of those pictures on the back of a place mat that tells you to find all the differences between two pictures that are very god damn similar but you always miss one. “Teardrops on my Guitar” is like listening to a recording of the way you feel when you realize you’re just not going to find that last difference, and the six-year-old next to you found it ages ago. 

One of them makes a steel guitar go, “wee-ooo” and the other has a click track.

What I find amazing about this album so far is that people enjoy it. “Teardrops on my Guitar” features three noises and they are all boring. There’s a guitar… solo? Break? I don’t know. It’s bad. Also, who the fuck is Drew? Why am I thinking about Drew? I don’t know Drew. I don’t want to know Drew. This is none of my business. 

This is how she gets you. You hear, “Drew” and you go, “oh damn, who the fuck is Drew?” I haven’t heard any of her music, but even I know her songs are not subtly autobiographical. It makes me… uncomfortable. Why doesn’t she have to put one of those “any relation to anyone living or dead is purely coincidental” disclaimers on her songs? I feel voyeuristic now that I know that Drew is a real dude. Well, he was. Now he’s Drew, the guy from that Taylor Swift song. Drew is dead. Long live Drew.  


“A Place In This World” sounds like the opening theme for an anime about teen girls that play in the tennis club and fight demons.


I got this from Genius

“Cold as You” is the fifth track of Swift’s debut album and details her experience with an emotionally unavailable guy. Unlike Shakespeare who compares his lover to a summer’s day Swift compares her lover to a cold, rainy day.

Yea, I guess. That’s… that’s true. Yea.


“The Outside” is officially 3 minutes and 29 seconds long, but in the way that Jodie Foster traveled through space for only a little bit but then couldn’t explain those 18 hours of empty recording.

It’s a perfect song. You get it, right? She’s on the fucking outside. I’ve been on the outside, you’ve been on the outside, we’ve all been on the Gods Damned outside! Fine!

It’s also a terribly produced song. I feel personally offended by the drum track here. This is boring shit and I hate it. Why is Taylor Swift’s music bad? Cause the music is bad. She’s incredible, her voice is perfect, her songwriting is such that it’s hard to find her unrelatable, but her music is fucking unlistenable.


A brief note on my style of reviewing: I only have two ratings. I don’t give out stars or scores or any other nonsense like that. Music for me is either listenable or unlistenable. 

Do you know how much music there is? It’s fucking incredible. People talk about peak TV or peak blah or peak blurgh, but we are living in maybe the best era for music in history. There’s more talent, more access, more freedom, more experimentation than ever. Without the gatekeepers and Barry Gordy fucking everyone up all the time, music is everywhere and everything all the time! 

Why the fuck would you waste your time on even a mediocre album?!

Either listen to it, love it, enjoy it, unabashedly tell everyone about how amazing it is, or ignore it, pretend it never happened, never listen to it again. 

Unless you suddenly have the urge to shit all over an artist because she had the gall to be very talented and surrounded by people who don’t actually like music, then go HAM.


From Genius:

“Tied Together With A Smile” is a song about a friend of Taylor’s with an eating disorder.

Noooope. I’m too old to say anything about anyone with an eating disorder other than I understand what you’re going through is very hard, super sorry and I wish you the best.


“Stay Beautiful” introduces Corey, a guy who does not understand that Taylor Swift wants to fuck him. Sorry, Corey, you dumb bastard, you blew it with Taylor fucking Swift. That’s actually very funny. See? This song about unrequited love is actually a song about a missed opportunity to steal some shit from Taylor Swift’s room and auction it fifty years later for a billion dollars.

Also I think she might’ve stolen the guitar track from every other song on this album. I would like to be a studio musician for Swift. I bet it takes a day, tops.


A little pet peeve of mine with lyrics sites; look, I understand wanting to be accurate and thorough, but these aren’t lyrics:

“Oh, oh, oh

Oh, oh, oh

Oh, but if it don’t

Stay beautiful

Stay beautiful

Na, na, na, na, na”

Just leave them out, we can figure out “oh oh oh oh oh oh oh” on our own. 


“Should’ve Said No” is a great example of why everyone likes Taylor Swift. The way she sings,

You should’ve said, “No”

You should’ve gone home

Is really powerful. I’m so angry with her. I’m nodding along saying, “Yes, get ‘em! GET ‘EM!” She hits it hard and the simple rhythm of “bah dump ba dum dum / bah dump ba dum dum” with an eighth note break between is wonderful composition. 

It’s also a great example of why I particularly find her unlistenable. This is the banjo tablature for the intro:

It’s not that it’s simple, or uncomplicated, or easy; it’s the pointlessness of it. It does nothing, it adds nothing, it doesn’t introduce a theme or element or anything. Music can be anything! 

Don’t make it nothing.


“Mary’s Song (Oh My My My)”: Fastball did it better.


In regards to Our Song, Swift said, 

I just sat down one day with my guitar and got in a groove, and went with it. I like to write about how music affects people, and this was fun to write because it’s about a couple who DOESN’T have a song. I like the banjo and you really can’t go wrong with banjo. I wanted it to be last on the album, because the last line of the chorus is `play it again’. Let’s hope people take it as a hint to go ahead and play the album again!

I don’t understand how it’s acceptable to let a 17-year-old talk about their music.

“I just want to thank God for letting me play at such a high level, I left it all on the field. It’s a team sport, not an individual sport and my team really stepped up today,” is all I hear when anyone under the age of 27 or over the age of 45 talks. 

I am a simple man with complex prejudices. And the banjo on this track fucking sucks, in case you were wondering.


When I first read the lyrics to “I’m Only Me When I’m With You” I was like, oh boy, this sounds like a toxic, codependent relationship and she needs to get out of it, but then I read more about it and found out it was about her and her best friend and I immediately thought of this (much, much better) song by Courtney Barnett. 

How’s that friendship doing now that you got a billion dollars, huh?

(Don’t judge me, I’m so bitter and old and this was written during the disastrous year of 2020)


Put “Invisible” over the credits of whatever 90s Disney animated movie you want and it works perfectly.

Except for Mulan, I’m obviously ride-or-die for 98 Degrees.


Ok, I’ve already covered “Teardrops on my Guitar” and how it’s unlistenable garbage in country OR pop form, so “Perfectly Good Heart” is the last track for this review.

This album is exhausting. But I understand her career and in fact, the world, much better. She has a perfect voice and a talent for hooks that make you whistle, get stuck in your head, and then sand you down like the ocean until your brain is smooth. 

This album has 5 great hooks by my count, 3 karaoke-ass scream jams, and endless examples of her ability to use tempo, rhythm, and breath control to communicate emotions.

Unfortunately, it really is terrible music. For years, it’s been a punchline in movies and TV and books and every corner of culture to laugh at the diminished masculinity of a man that listens to and loves Taylor Swift. 

I have often wondered if part of the reason I’ve avoided her is because I am afraid of appearing to have diminished masculinity. I feel that I’ve avoided her because I don’t want to engage in that shit at all, but that would absolutely be something someone afraid of appearing to have diminished masculinity would say, so judge for yourself.

What it is, I think, is that I was honestly so much of an asshole about music when I was younger that I retired into the musical mountains like a Han Shan, refusing to judge anyone for liking anything unless they climbed that whole fucking mountain and forced me to judge them for their music. 

But I’ve come down from that mountain and “Perfectly Good Heart” makes me want to bully people. Like, hey, either you’re her writing that song, in which case ugh, fuck off, or you’re someone listening to that song, in which case, ugh, fuck off.

Welp, I went as long as I could without criticising her lyrics.


I am done! I know I was hyperbolically mean, but no one should feel shame or diminished masculinity for listening to Taylor Swift. She’s a superstar and I understand how you can get sucked into her vortex. I don’t judge you for it, in the same way I don’t judge the Nazis for just “following orders.”

My rating of Taylor Swift’s first album, “Taylor Swift” is, out of two possible answers, unlistenable. I will never listen to it again for as long as I live. 


Honestly, though, it’s not that bad. Most of the reviews have it as a 6 or 7, slightly above average, and I’d agree with that.

Jordan Holmes is a Chicago comedian and author and the cohost of the Knowledge Fight podcast, which takes an in-depth look into Alex Jones and Infowars. You can download his first novel, The Quiet Part Loud, available in both written and audiobook format, and

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