I seem to be doing these pop culture posts every other week, so today is probably the last time I’ll do one before the release of Taylor Swift’s new album, The Life of a Showgirl on October 3. So in honour of that momentous pop cultural event, in today’s deep dive, I’ll talk about my history with Swift’s work and her impact as an artist. But first, the cultural roundup for the past two weeks.
Roundup
Music
Nothing has really blown me a way the past couple weeks, though there have definitely been some albums I want to spend more time with. One notable exception to the general ‘meh’ was the highly anticipated release of JADE’s THAT’S SHOWBIZ BABY! last week. It’s a strong album that suggests the former member of Little Mix could have some legs as a solo artist. Another noteworthy release was The Dream, by The Favors (comprised of mononymic artists FINNEAS and Ashe).
Songs
- “Thirst Trap,” by Audrey Hobert
- “Self Saboteur,” by JADE
- “Secrets,” by Miley Cyrus (featuring Lindsay Buckingham and Mick Fleetwod)
Albums
- THAT’S SHOWBIZ, BABY, by Jade
- The Dream, by The Favors
- Girl Violence, by King Princess
Reading
My big Booker-list push may be over, but that’s just the beginning of literary prize reading season, so my reading has continued to be dominated by literary fiction the past couple weeks, with some lighter fare sprinkled in to leaven that heaviness. Highlights have included (Leonard and Hungry Paul, by Rónán Hession (2019), F, by Daniel Kelhmann (2013), Scorpionfish, by Natalie Bakopoulos (2020), and The Remembered Soldier, by Anjet Daanje (2019, transl. 2025; from the National Book Award for Translated Fiction longlist).
Viewing
I’ve been enjoying the new season of Project Runway, so I’ve been checking out earlier seasons, many of which are available from the series’ official YouTube channel. It’s good background watching, but it’s remarkable to me how much more reality-tv-like the newest season is. Former cohost/mentor Tim Gunn always said he loved the format because it was all about the clothes and they spoke for themselves, but this new season (minus Gunn) has been very production-heavy, which makes me sad.
In Focus: Taylor Swift and Me
When Taylor Swift first appeared on the music scene, I was a 26 year-old man who listened to indie rock and remixes of vintage jazz standards. In other words, I was in pretty much the worst demographic to take notice of a teenage girl with a guitar singing country songs (in an untrained voice) about high school. So, rather than encountering her through her music, I first encountered her through the negative and dismissive media narratives surrounding her: ‘Taylor Swift can’t sing.’ ‘She only writes breakup songs.’ ‘Beautiful gowns….’ Not to mention the Kanye incident at the 2009 VMA Awards. I can’t say I remember hearing a song of hers until the inescapable ‘Shake it Off’ and ‘Blank Space’ in 2014.
This all changed for me in 2020 with the release of Folkore. My best friend, himself far from a Swiftie, messaged me that morning telling me I had to drop everything and listen to the album immediately. I can’t say I was immediately won over, but I could tell there was something substantial there that I wanted to spend more time with. And when I did, I was simply astonished by the quality of the songwriting. And that made me wonder what had I missed in my media-driven dismissal of her earlier work. And so, I made a point of familiarizing myself with it. And again I was amazed, most especially by how much her songwriting rewards careful and repeated listening. And now, five years later, I am pretty much convinced that she’s incapable of writing a bad song, even if some might not be to one’s taste.
Moreover, in her extensive catalogue, she’s built up a whole universe of storytelling, with lines in a song from 2024 elucidating the meaning of a song from 2022 that called back to a song from 2012. Even if, like me, you’re not into the celebrity drama of it all, this turns her discography into an incredibly rich text.
Here, in the buildup to the release of her twelfth studio album, is my personal ranking of her albums:
11. Taylor Swift (2006, country): This album shows a lot of promise but also a lot of immaturity — in other words, it’s juvenalia, but juvenalia that happened to sell millions of copies. It seems clear at this point she was instructed to ‘country things up’ in order to pass muster in Nashville, so a lot of it feels performative (the constant references to small towns and trucks, for example, to say nothing of the affected accent). But there’s still a core of strong, if not fully baked yet, songwriting on a lot of these songs. It’s the only album that doesn’t work for me — but she was 16 when it was released, and much younger when she wrote a lot of the songs, so it’s incredibly impressive nonetheless. I’d be fascinated to see what she could do with these songs today, with her more mature and better-trained voice, and with less dated production.
- Biggest Hit: “Tim McGraw”
- Best Song: “Our Song”
- Best Lyric; “Our song is a swinging screen door…”
- My Favourite Song: “Teardrops on My Guitar”
10. Speak Now (2010, country, pop punk rock): Swift’s third album received tepid reviews and didn’t make the impact her second album had. But it features some of her best and most memorable song-writing (’You made a rebel of a careless man’s careful daughter’ (”Mine”), all of the lyrical evisceration that is “Dear John”). Where it falls for me is that it plays with some derivative ‘pop punk’ rock sounds that just aren’t as much to my taste.
- Biggest Hit: “Mine” (though in hindsight it’s “Enchanted” that seems to have stuck)
- Best Song: “Dear John”
- Best Lyric: “You made a rebel of a careless man’s careful daughter”
- My Favourite Song: “Mine”
9. Fearless (2008, country): It’s Swiftie blasphemy to have her second album, for which she won her first Album of the Year Grammy, ranked so low. But while the best songs on the album are undeniable, the quieter songs largely feel like filler to me, so it suffers on average.
- Biggest Hit: “Love Story”
- Best Song: “Fearless”
- Best Lyric: “Made you run and hide like a scared little boy”
- My Favourite Song: “Fearless” (honorable ‘from the vault’ mention: “Mr. Perfectly Fine”)
8. Evermore (2020, indie): It says a lot about just how strong of an artist Taylor Swift is that an album I legitimately love only ends up eighth in my ranking. It suffers mostly by coming so quickly on the heels of Folklore, making comparison inevitable. It’s a bit more experimental in its sounds and storytelling but just doesn’t quite hit the same highs/ but make no mistake: it’s a special album.
- Biggest Hit: “willow”
- Best Song: “ ‘tis the damn season”
- Best Lyric: “I know my love should be celebrated, but you tolerate it.”
- My Favourite Song: “long story short”
7. Red (2012, country, country rock, pop): Despite her reputation, this is really Swift’s only true breakup album, and both thematically and sonically, it captures the emotional whiplash of the end of a toxic relationship. It’s also the first of her albums to have songs that were purely in the pop genre. The highs on this album are really high (including the all-time fan favourite and arguably her best-written song, “All Too Well,” which is wistful in its original version and scathing in its expanded, ten-minute version), but there’s just too much filler on it for me for it be ranked higher.
- Biggest Hit: “We Are Never Ever Getting Back Together”
- Best Song: “All Too Well” (10 minute version)
- Best Lyric: “And you call me up again just to break me like a promise / So casually cruel in the name of being honest”
- My Favourite Song: “All Too Well” (10 minute version) (honorable mention: “Treacherous”)
6. Reputation (2017, pop): Produced in the aftermath of her ‘canceling’ following the over-exposure of the 1989 era and the (doctored) Kim/Kanye tape (in which it appeared she agreed to a lyric in one of Kanye West’s songs she later publicly denounced), Reputation shows just how smart she is. Instead of pushing back against the media narratives, she leaned heavily into them, even adopting the snake in the album’s iconography. Much darker in both theme and sound than her previous work, it wasn’t well received upon first release, but is now viewed as part camp classic, part ode to finding unexpected love in a dark time.
- Biggest Hit: “Delicate”
- Best Song: “Getaway Car”
- Best Lyric: “We can’t make any promises now, can we babe? But you can make me a drink.”
- My Favourite Song: “Getaway Car”
5. Lover (2019, pop): Most artists use their singles to heighten expectation and anticipation for the upcoming album; Swift sometimes seems to use them to throw people off the scent. If Lover is viewed as something of a flop, it’s mostly because its two singles are widely viewed as two of the worst songs in her discography. But behind them is an effervescent album of songs about love in its many forms.
- Biggest Hit: “Cruel Summer”
- Best Song: “Cruel Summer”
- Best Lyric: “I once believed love would be burning red, but it’s golden.”
- My Favourite Song: “Cruel Summer” (honourable mention to “Death by a Thousand Cuts”)
4. Midnights (2022, pop): After the indie turn in her 2020 albums, and in the midst of her ‘Taylor’s Version’ re-recording project, no one knew what to expect from Swift’s tenth studio album. What we got was a strong, introspective (if opaque), shimmering pop album that earned her her fourth Album of the Year Grammy. The highs are so high (it has five of my favourite twenty songs in her extensive discography) that I can forgive a bottom half I find pretty forgetful.
- Biggest Hit: “Antihero”
- Best Song: “Maroon”
- Best Lyric: “I made you my world / Have you heard? / I can reclaim the land.”
- My Favourite Song: “You’re On Your Own, Kid”
3. The Tortured Poets Department (2024, pop, folk/indie): One of the criticisms leveled against Taylor Swift has been that she’s obsessed with controlling the narrative surrounding her. I’m not sure anyone can that after her 2024 double album, in which she writes honestly about events that don’t paint her in a positive light, what she has referred to as “temporary insanity” and “self-inflicted wounds.” The resulting album is melodramatic and a little all over the place, but intentionally so. At thirty-one tracks, it definitely feels bloated, but here’s the thing: they’re all good songs. Everyone seems to agree they’d have preferred a 20-track album, but there’s nothing close to a consensus on the songs that should be cut. For me it ranks this highly because of this quality. It’s not an album I listen to front to back, and I have my share of skips, but when I do listen to them I can’t deny they’re great songs.
- Biggest Hit: “Fortnight” (but only because it was the first of only two singles)
- Best Song: “loml”
- Best Lyric: “Who’s gonna stop us from waltzing back into rekindled flames / when we know the steps anyway”
- My Favourite Song: “Guilty as Sin” (honourable mention to “loml” and “The Black Dog”)
2. Folklore (2020, indie/folk): The album that started it for me. When the rest of us were doom-scrolling and making banana bread in 2020, Taylor Swift, facing the pandemic cancellation of her Loverfest tour, got to work. And, after three and a half albums working in a pop idiom, she took a huge turn and created a folk/indie masterpiece that earned her her third album of the year Grammy.
- Biggest Hit: “Cardigan”
- Best Song: “My Tears Ricochet” (to me the song that could give “All Too Well” a run for its money as her best songwriting)
- Best Lyric: “I didn’t have it in myself to go with grace”
- My Favourite Song: “My Tears Ricochet”
1. 1989 (2014, pop): Swift’s first pure pop album, 1989 is to my mind the perfect, quintessential, pop album. Produced largely by noted hitmaker Max Martin (with great song-level contributions from Imogen Hoep and Jack Antonoff to shake things up), this is a literal no-skip album. Not only are these songs all incredibly fun, but they don’t sacrifice lyricism and meaning in the process. Pull back the veil of “these sick beats” and you’re left with a fascinating collection of songs about youth, fame, and contemporary dating.
- Biggest Hit: “Shake It Off”
- Best Song: “Style”
- Best Lyric: “Didn’t you calm my fears with a Cheshire Cat smile?”
- My Favourite Song: “Style”
Matthew Root 