Press "Enter" to skip to content

An MBAs guide to Taylor Swift’s discography22 min read

About two weeks ago, we got an email from our Editor-in-Chief with deadlines for the May Oppy release. Usually, Deirdre Keane, DNP, MSN, FNP-BC, NP-C, CCRN, CPN, WCC’s e-mail signature screams enough “Yes you do have enough time to write” on its own, but this came with an extra plug: 

“For those of you graduating, remember this is your last chance to leave your legacy.”

Legacy? The best part about my experience with the Oppy is pretending to know how to write while practicing on pretty much whatever seems fun. I’m happy to take advantage of the editorial discretion while I can. 

Anyways, I’m just the website guy. Y’all can write about B-School stuff next year. Meanwhile, I’ll try my hand as record critic. Taylor had a big year – let’s update the rankings.

Group 15: Could Have Stayed in the Vault

A Perfectly Good Heart, Afterglow, Begin Again, Change, Cold as You, Daylight, Don’t You, Dress, False God, Gorgeous, Haunted, How You Get the Girl, I Almost Do, I Think He Knows, Innocent, It’s Nice to Have a Friend, Jump Then Fall, King of My Heart, Lover, Me!, Sad Beautiful Tragic, So It Goes…, Soon You’ll Get Better, Superstar, The Archer, The Best Day, The Last Time, Tied Together with a Smile, Treacherous, Untouchable, We Were Happy, You All Over Me, You Are in Love, You Need to Calm Down

Even our most prodigious artists have tracks they probably could have held back. Each of the songs in this catch-all bucket was, like a fleeting 2010s Swift lover, ultimately just that: fleeting. 

It’s no secret Swift’s early lyrics have aged better than others. Breakout albums Taylor Swift, Fearless, and Speak Now are forces of music, but, like any great records (I adore Abbey Road yet could not tell you a single thing about “Polythene Pam”) they had their winners and losers. Many in this group evoke a sing-song immaturity or too-early attempts at real emotional depth (It’s not unbroken anymore / How do I get it back the way it was before). Either can be cringe-worthy.

Reputation had its moments, but few will defend the blunted and overproduced album in the grand scheme of Swift’s career. Most of the time, it felt more like a vessel for Swift’s experimentation than fan service. Lover, while not a bad album, is easily Swift’s least memorable. 

We’ll cover what matters. Let’s get into it.

Group 14: Reputation (Killers) 

127 End Game (Reputation)
126 …Ready for It? (Reputation)
125 Look What You Made Me Do (Reputation)
124 I Did Something Bad (Reputation)
123 Don’t Blame Me (Reputation)
122 Dancing with Our Hands Tied (Reputation)

This tier could also have stayed in the vault, but these six from Swift’s shakiest period to-date deserve their own callout. Reputation was released in 2017 and sold 2 million units in its first 18 weeks. Swift’s prior three albums each sold 2 million units, in their first 14 weeks combined. The Reputation singles were… surprising? Surprisingly harder to listen to than you expected? 

Defenders of Reputation-era Swift point to the “vulnerability” of her lyrics or the “boldness” of a new direction. Listen, I’ve got about another 3,000 words gushing about Taylor’s music, but she isn’t Sam Cooke. The relative depth of Swift’s music makes her a standout popstar, but she isn’t challenging the moral fabric of society. It’s hard to hear the impact behind Ed Sheeran and Future raps.

At the end of the day, her music gets more attention than her message. In Reputation, Swift tried drawing her own line in the sand between Old and New Taylor, with mixed results. This group was the first stain on Swift’s hit-making record.

Group 13: The Christmas Album

121 Christmas Tree Farm (Sounds of the Season: The Taylor Swift Holiday Collection)

Do you think Swift had any idea where she was on her career arc when she released Sounds of the Season: The Taylor Swift Holiday Collection? Still relatively under the radar, I am sure a young Swift aspired for more than bringing “a new generation of sensitive girls [to] discover the melancholy but oh-so-melodic ‘Last Christmas.’” 

Regrettably, the whole thing feels a bit more late-stage Bublé than rising-star Swift. I think she’d want us to exclude most of this EP. “Christmas Tree Farm” is alright, though.

Group 12: Folk-More B Sides

120 Invisible String (Folklore)
119 Happiness (Evermore)
118 Closure (Evermore)
117 Hoax (Folklore)
116 Exile (Folklore)
115 Evermore (Evermore)
114 Peace (Folklore)
113 Seven (Folklore)
112 Epiphany (Folklore)
111 Willow (Evermore)
110 The Lakes (Folklore)
109 Dorothea (Evermore)
108 Marjorie (Evermore)
107 Cardigan (Folklore)

Swift re-emerged from Lover with a quarantine one-two punch.  Right as folks finished penning praise for the return of Old Taylor on Folklore, the master of hype kept her streak alive with Evermore’s prompt release. Swift opened up the full public relations repertoire: “spontaneous” releases, curated sub-album “chapters,” mysterious characters that may-or-may-not-be fictional, cryptic lyrical segments that wind across multiple tracks. At this point in her career, Swift has an Elon Musk-like ability to string along both fans and foes alike.  

Even so, stretching Folklore and Evermore into 34 tracks feels like turning The Hobbit, the standalone novel, into three movies. Sure, it’s all rooted in great content, but it was  intended as a single story. We can blame Swift spending too much time with Bon Iver.

An album release with these fourteen tracks would not have inspired a Swift renaissance. They are the B Sides – good for deeper listening when you’re in the groove, but they don’t stand on their own.

Group 11: Probably Won’t Skip it but Probably Won’t Search it on Spotify Either

106 Starlight (Red)
105 I Forgot That You Existed (Lover)
104 It’s Time to Go (Evermore)
103 Everything Has Changed (Red)
102 Illicit Affairs (Folklore)
101 Wildest Dreams (1989)
100 Death by a Thousand Cuts (Lover
99 Only the Young (Non-album single)
98 The Lucky One (Red)
97 Tolerate It (Evermore)
96 Never Grow Up (Speak Now)
95 I Know Places (1989)
94 The Moment I Knew (Red)
93 Girl at Home (Red)
92 Ivy (Evermore)
91 Red (Red)
90 Superman (Speak Now)
89 My Tears Ricochet (Folklore)
88 This Love (1989)
87 Welcome to New York (1989)
86 Better than Revenge (Speak Now)
85 The 1 (Folklore)
84 Clean (1989)

Pretty self-explanatory. Even flawed tracks have redeeming qualities. For example, you might queue up “Welcome to New York” while driving across the GW Bridge, but otherwise it’s actually a tad annoying. Frankly, we needed some clean-up to tackle the sprawling 160-song discography. We’ve got 80 to go. Not much more to say here.

Group 10: PBRs

83 Mean (Speak Now)
82 Invisible (Taylor Swift)
81 A Place in This World (Taylor Swift)
80 Mary’s Song (Oh My My My) (Taylor Swift)
79 That’s When (Fearless)
78 I’m Only Me When I’m with You (Taylor Swift)
77 The Outside (Taylor Swift)
76 Come in with the Rain (Fearless)
75 Stay Beautiful (Taylor Swift)
74 Fifteen (Fearless)
73 Bye Bye Baby (Fearless)
72 The Other Side of the Door (Fearless)

This group’s a too-cool-for-Bud Light 12-pack of classics, so long as your palate isn’t too refined. 

(When you’re 15 and someone tells you they love you, you’re gonna believe them)

(All I want is you / To stand outside my window throwing pebbles screaming I’m in love with you)

(Take me back to the house in the backyard tree / Said you’d beat me up, you were bigger than me)

These lines aren’t winning any Pulitzer’s, but they are timelessly catchy and hint at the dominant pop force that Swift was incubating as a “country” musician. 

Group 9: Miss Americana 

71 Bad Blood (1989)
70 Enchanted (Speak Now)
69 Miss Americana & the Heartbreak Prince (Lover)
68 Paper Rings (Lover)
67 The Man (Lover)
66 London Boy (Lover)
65 Cornelia Street (Lover)
64 If This Was a Movie (Speak Now)
63 Breathe (Fearless)
62 State of Grace (Red)
61 Speak Now (Speak Now)
60 Holy Ground (Red)
59 Come Back… Be Here (Red)
58 Long Live (Speak Now)
57 Back to December (Speak Now)
56 New Year’s Day (Reputation)
55 Stay Stay Stay (Red)
54 The Story of Us (Speak Now)

Through Netflix documentaries, songs, interviews, Swift has really latched onto the ‘Miss Americana’ title. Got to love the audacity of declaring yourself an artifact in the United States’ cultural heritage, but we’ll play along. 

These songs are the background of Swift’s career. They aren’t the play-on-repeat singles; they’re the B-plus quality songs that only an artist of Swift’s caliber could accumulate in such numbers. They are the bread-and-butter of her catalog, and unfortunately the most difficult selection of songs to sort out. Swift’s a popstar, and her theme, ultimately, is “hits.” Inevitably, you reach the point of having too many “good” but not unique songs to spread out over 160 slots. 

Group 8: Reputation (Savers)

53 Delicate (Reputation)
52 This Is Why We Can’t Have Nice Things (Reputation)
51 Call It What You Want (Reputation)
50 Getaway Car (Reputation)

Even as Swift’s producers took the heavy electronica of 1989 off the deep end, Reputation was not entirely lost. Swift and Co salvaged four quite good songs from an otherwise adventurous album. Fortunately, Swift and Antonoff did recapture some 1989 synth-pop magic with “Call It What You Want”. “Delicate” similarly benefited from not trying to do too much. Even “This is Why We Can’t Have Nice Things,” one more track borne of Swift’s affixation with Kanye West, is an absolute blast of an arena play. 

Swift obviously recovered just fine from any post-Reputation slump. With plenty of albums before and after, you can pick up the best tracks and move on. At best, the record was an admirable experiment in vulnerability and escaping your critics. At worst it was the kind of mistake you correct by firing your agent.

Group 7: Gold Rush

49 Mad Woman (Folklore)
48 Right Where You Left Me (Evermore)
47 Mirrorball (Folklore)
46 Gold Rush (Evermore)
45 Long Story Short (Evermore)
44 Tis the Damn Season (Evermore)
43 Cowboy Like Me (Evermore)
42 The Last Great American Dynasty (Folklore)
41 Betty (Folklore)

In Group 12, I lamented Swift’s prodigal output in 2020. Here, let us marvel at it. While you were scrolling Instagram during Zoom class last year, Swift wrote and recorded 34 brand new songs, plus re-recorded 26 songs – out of spite – for a total of three Number 1 albums in the span of 259 days (The Beatles took 364 days, but who’s counting).

Nobody can nurse the release hype cycle like Swift. It is a Galloway-sized case study in perfectly timed marketing. This is an artist who feeds the internet with “hidden” messages “’subtly” CAPITALIZED in album booklets; she reserves a room in her head for Kanye West simply because the internet loves it. Group 7 shows that hype cycle at its finest. Track after track that poured out of Folk-More was played and lauded and repeated.  

What’s most remarkable is how plainly they stand on Swift’s talent alone. There’s no heavy pop production to fall back on, no catchy melodies. This is bard Swift, on the piano with maybe five chords, telling stories with increasingly poetic lyrics.

“To put it plainly, we just couldn’t stop writing songs,” Swift said. We’re glad you didn’t. 

Group 6: The Ones That Got Away

40 Last Kiss (Speak Now)
39 Ours (Speak Now)
38 You’re Not Sorry (Fearless)
37 Dear John (Speak Now)
36 Tell Me Why (Fearless)
35 Picture to Burn (Taylor Swift)
34 Teardrops on My Guitar (Taylor Swift)
33 Forever & Always (Fearless)
32 Hey Stephen (Fearless)
31 The Way I Loved You (Fearless)
30 Mine (Speak Now)

Group 6 should be a familiar bunch. Swift has perhaps no four words more famous than “Drew looks, at me.” Her trademark songwriting, despite steps in more adventurous directions, revolves around lost love. 

This is not a fault. Few songwriters can extract enough depth from the topic, let alone weave into melody. Few can kick jilted lovers while they’re down like Swift (You’re a redneck heartbreak who’s really bad at lying). Few ballads hit so unexpectedly like Swift’s (I’ll watch your life in pictures like I used to watch you sleep / And I feel you forget me like I used to feel you breathe).

And no one spins more songs about love lost, spurned, and embraced in the rain. 

(I miss cursing and crying and screaming in the rain)

(I rains in your bedroom / Everything is wrong / It rains when you’re here / And it rains when you’re gone)

(Can’t help it if I wanna kiss you in the rain)

(I do recall now the smell of the rain / Fresh on the pavement)

Group 5: Liberal Arts College Frat Bangers

29 I Knew You Were Trouble (Red)
28 Sparks Fly (Speak Now)
27 We Are Never Ever Getting Back Together (Red)
26 22 (Red)

Group 5 is the track list most likely to be yelled in an off-campus basement circa 2013. “I Knew You Were Trouble”, “We Are Never Getting Back Together”, and, of course “22”: these are coming-of-age anthems. There is admittedly not much depth to discuss, but they are staples in any Swift collection.

Group 4: Prodigy

25 Today Was a Fairytale (Fearless)
24 Should’ve Said No (Taylor Swift)
23 Mr. Perfectly Fine (Fearless)
22 White Horse (Fearless)
21 Tim McGraw (Taylor Swift)

Groups 4 and 3 highlight Swift’s best work from opposite ends of her career. 

“Tim McGraw” was Swift’s first foothold in the music industry. “The song means so much to me and that’s why we wanted it to be the first track on the album,” said Swift. She wrote it as a high school freshman, about a high school senior, in an alleged 15 minutes. Ever since, you can’t hear “Humble and Kind” without thinking of Swift (When you hear Tim McGraw, I hope you think of me).

Receiving newfound attention in the remastered Fearless: Taylor’s Version, we are reminded just how many hits there were in these nascent steps of Swift’s career. Even “Today was a Fairytale” has roared back to attention after debuting in the (extremely forgettable) rom-com Valentine’s Day

Sophisticated enough and timelessly singable, these tracks set Swift on a path of astronomical success. There was no looking back.

Group 3: Folk-More’s Greatest Hits

20 Champagne Problems (Evermore)
19 August (Folklore)
18 This Is Me Trying (Folklore)
17 No Body, No Crime (Evermore)

At the other end of her career, we have Swift in total control of her talent. Doubled down on her strengths, these songs are everything Swift is good at without trying anything provocative. Unlike earlier attempts at this “stay-in-your-lane” approach, however, Swift now commands something much wider than backcountry singalongs.

circa 2010: Can you feel this magic in the air? It must have been the way you kissed me

circa 2020: Your Midas touch on the Chevy door / November flush and your flannel cure

There’s a difference between a teenage songwriter and a songwriter in her thirties. If Group 10 are the PBRs of Swift’s catalog, Group 3 are the Macallans. Even simple lyrics (August slipped away like a bottle of wine) feel well-crafted and intentionally mapped.

Finally, this group brings us the Swift collaboration we needed most. Swift and close friends Haim upstage Carrier Underwood and countless others with unexpected country ballad “No Body, No Crime”. You can feel how much fun they had making this song. And it’s excellent.

Group 2: The Last Great American Pop Album

16 Style (1989)
15 Shake It Off (1989)
14 Blank Space (1989)
13 I Wish You Would (1989)
12 Wonderland (1989)
11 All You Had to Do Was Stay (1989)

If Groups 3 and 4 bookend Swift’s career to date, Group 2 is the apex along the way.

1989 was released on October 27, 2014. I was studying in Australia at the time, so the album dropped at some obscure hour halfway around the world. I listened to it twice. Maybe I was just homesick and single. But it was ****ing good. 

A year later, back in the States, Swift still owned pop music. 1989 produced all seven of these tracks as music video singles, each one a statement success (well, Wildest Dreams was a misstep). The 1989 World Tour was the highest-grossing tour of 2015. According to Billboard Magazine, 1989 “ruled radio for a year and … achieved a kind of cultural omnipresence that’s rare for a 2010s album.” 

It’s nearly impossible for a song to catch faster than the 10-second intro to “All You Had to Do Was Stay”. Another 25 seconds and you’re already into the first hook. By then, you’ve already decided to listen to the song again. That’s a pop song.

Swift and her Swedish producers found the upper limit of synth-pop and EDM in “Wonderland.” Unlike later attempts, it works. Not the first song you replay, “Wonderland” is the high octane track that keeps you going once the rest of the album is exhausted.

Speaking of exhausted tracks – “Shake it Off”, while critically questioned, is Swift’s most commercially successful single to date. It was also the lead single from 1989 that kicked off The Year of Taylor. “Blank Space”, Swift’s second-most dominant video single, was the first accelerant. I personally think she has better songs, but we cannot ignore them.

Group 1: The Top Ten

10: Out of the Woods (1989)

1989 was the pinnacle of Swift’s career (albeit not entirely on her own terms) and is the rare example of a pop star that dominates on a scale larger than single release cycles. If we had to pick one single, however, it must be “Out of the Woods”.

Swift’s knack at injecting imagery while remaining catchy (Decided to move the furniture so we could dance, Baby like we stood a chance) is in full force, with the indietronica instrumental support to push it to new heights. Instead of drowning out the lyrics in a confused mess, producer Jack Antonoff punches home every word with simple synth riffs and cascading bass drums. Besides a pretty weird music video, “Out of the Woods” is the glowing capstone on a project for the ages.

9: Stay Stay Stay (Red)

If 1989 was the pinnacle of Swift’s career, Red was camp halfway up the mountain. “Stay Stay Stay” connects Swift’s teenage albums with Red, a transformative step up that added new depth and nuance to Swift’s discography. Swift’s early songs put a tune in your head; in Red, she planted the imagery to go with them. 

“Stay Stay Stay” recounts a tale as old as time – young love in trouble (I’m pretty sure we almost broke up last night). Swift’s focus on ostensibly trivial details – carrying groceries, wearing football helmets – makes the story memorable. And it’s catchy. Swift gets few accolades for her vocals, but she can work two notes with the right see-saw pace to keep you engaged, nonetheless (You took the time to memorize me / My fears my hopes and dreams / I just like hangin’ out with you, all the time).

Red’s release brought Swift from teen phenom to a force of lyrical narration. “Stay Stay Stay” made that transition seamless.

8: Cruel Summer (Lover)

Easily Lover’s best track, “Cruel Summer” was more importantly Swift’s strongest release since 1989. It was a pivotal track for Swift at a time when she wasn’t churning out hit music video after hit music video. 

But “Cruel Summer” is independently strong, too. It sounds like a Swift pop hit. Just four lines after the track opens (Fever dream high in the quiet of the night / You know that I caught it), Swift wastes no time jumping into the hook and its off to the races. 

The playful, question-marked tone that changes up before each hook (Devils roll the dice, angels roll their eyes / What doesn’t kill me makes me want your more); the screamed (I don’t want to keep secrets just to keep you) that breaks up the bridge; the always roaring chorus (It’s a cruel summer). Swift pulls out the full pop repertoire for a song touted as “ethereal” and “infectious.” Can’t argue with that. 

7: Coney Island (Evermore)

This ranking’s hottest take: “Coney Island” was the best Swift song of 2020. (Full disclosure: those of us from Ohio can have perverse inclinations toward Buckeye music acts. The Swift-National collaboration has been a long time coming).  

The track starts slow, until Swift cuts away and Matt Berninger’s baritone rumbles in like the creeping doubts of a career coach (The question pounds my head / What’s a lifetime of achievement). It’s all climb from there.

Pop duets usually don’t add any more value than an extra name on the song title. “Coney Island” is not any pop duet. Borne from a months-long production partnership between Swift and the National’s Aaron Dessner, Coney Island masterfully builds two very different vocalists into a single melancholy sound. The two complement each other; Swift’s allure drawing something catchier from of the depths of Berninger’s voice, Berninger’s baritone softening the edge for a mellower but still richly emotional sound.  

By the time Berninger takes Swift’s verse (We were like the mall before the Internet / … / The mischief, the gift wrapped suburban dreams) into the hook (Sorry for not winning you an arcade ring / Over and over / …) they are firing on all cylinders. With each call-and-response, the bridge gets heavier and heavier. Swift’s regret fades flawlessly into Berninger’s (Were you standing in the hallway / With a big cake, happy birthday / Did I paint your bluest skies the darkest gray, a universe away?).

It is the best song of her year, and Swift’s strongest duet ever. 

6: New Romantics (1989)

Warmer take: New Romantics is Swift’s most underrated track of all time. 

The five songs that follow were frankly some of the easiest picks to make. The durability of Swift’s early work – most notably Fearless, now in its second chart-topping campaign thirteen years after its release – is what makes her discography special. A pop artist’s top songs deserve to be her most ubiquitous.

But, inexplicably excluded from the 1989 culture blitz, “New Romantics” is a contender. Rob Sheffield of Rolling Stone asks the logical question: “I have no idea why [Swift] left a song this urgent and glittery and perfect off her album. But geniuses are weird. [This] is a work of genius, exceeding even the wildest hopes any fan could have dreamed.” (emphasis mine)

Rob loves it, and so should you. New Romantics is self-empowered, hook-to-the-face Swift at her finest (‘Cause baby I could build a castle / With all the bricks they throw at me). It’s a classic.

5: Love Story (Fearless)

4: Fearless (Fearless)

3: You Belong with Me (Fearless)

Nothing controversial here – these are the best songs on Swift’s best album. Making grade school lyrics sound this good (Baby drive slow, until we run out of road) is Swift’s talent uniquely. Her songwriting has matured enormously over her decade-plus career; her tracks today almost universally show a depth – both lyrically and musically – that run laps around her early work. And yet, people still pine for Old Taylor. 

“Fearless” ekes out “Love Story” purely on title track status, but they are both iconic songs on a similar rubric. Swift takes simple ingredients – relatable anecdotes, accessible vocal ranges, earworm melodies – and produces the very best sappy love possible. There are a million ways to write a love song with a middle school vocabulary and beginner guitar chords. You Belong With Me is the best you can do.

2: Our Song (Taylor Swift)

The Number 2 spot is for Swift’s best (only?) country song: “Our Song.” Wielding her twang and freshly cultivated Tennessee-girl image, Swift smashed the line between pop and country. The rest of her catalog is left indistinguishable. 

“Our Song” sets the perfect summer soundtrack for driving around high school jalopies and sneaking out to friends, lovers, and parties (‘Cause it’s late and your mama don’t know). By the way, can you imagine Swift casually slipping religion into a hook on her next album? We’ve come a long way since (asking God to play it again), but I’ll be damned if “Our Song” isn’t one of Swift’s very best. And before we dissect the word-choice too much, let’s remember that Swift wrote this song for a 9th grade talent show. 

1: All too Well (Red)

Legendary journalist and cultural critic Joan Didion espouses imagery and well-crafted sentences in the essay “Why I Write”:

To shift the structure of a sentence alters the meaning of that sentence, as definitely and inflexibly as the position of a camera alters the meaning of the object photographed. Many people know about camera angles now, but not so many know about sentences. The arrangement of the words matters, and the arrangement you want can be found in the picture in your mind. The picture dictates the arrangement.

Songwriter first and musician second, Swift knows about the sentences. Swift sees the pictures and arranges them like slides in a View-Master, clicking through them line by line. Iconic bridges, variable hooks, extra lyrical segments added here and there – these efforts stretch Swift’s hits from a stint of radio play to playlist favorites.

Swift layers verse after verse in All Too Well, releasing hits of dopamine with every guitar strum and pitch change. She turns her memories into your memories: on that little town street, down the stairs, in the refrigerator light. At its peak, Swift delivers the lyric she claims to be most proud of (You call me up again just to break me like a promise / So casually cruel in the name of being honest) and it’s a good one.

As the temperature simmers, Swift deftly recapitulates each anecdote (You remember it all) and immortalizes the most iconic scarf in pop culture (It reminds you of innocence / And it smells like me). The original take was “probably a 20-minute song.” Let’s hope she pulls it out of the Vault in Red: Taylor’s Version.

Mission News Theme by Compete Themes.